B2B 35 | TripleLift

B2B 35 | TripleLift


Our guest today defines go-to-market as a strategic iterative process of delivering a solution based on an opportunity in the market. To her, everything comes down to positioning. It’s all about understanding the goals of your clients so your product suits their needs. This is how Ali Wendroff approaches go-to-market strategy in her position as Senior Director of Global Engagement at TripleLift. In this conversation, she shares her journey from her first job in an ad tech company to her present leadership position in a global leader in the programmatic industry. Join in and learn about the ins and outs of go-to-market strategy in this fast-paced core industry!

Listen to the podcast here


Delivering Customer-Centric Go-To-Market Solutions In Programmatic Advertising With Ali Wendroff, TripleLift

In this episode, I have with me Ali Wendroff, who is the Senior Director of Global Engagement at TripleLift. I am excited to have you on the show.

No worries. Thank you so much. I’m excited to be here.

This is what I always start off the show with, and this is a very intriguing and interesting question. It takes the conversation in a lot of directions with the speakers and even the readers enjoy. Ali, how do you define go-to-market?

I put a lot of thought into this, but I would define go-to-market as a strategic iterative process of delivering a solution that’s based on a need or an opportunity that has presented itself in the market. I think what’s most important in terms of the go-to-market process is positioning. It’s all about your audience. It’s fully understanding the goals of your clients to ensure that the product or solution suits their needs and identified gaps.

I think it’s far from a one-size-fits-all approach, and it’s rather entirely about the voice of the customer, which varies even within an organization with whom you might be engaging with. If you can’t answer the why, why it matters, why your clients should care, why it solves a problem, why should they want it, and why it speaks their language not yours, then I don’t think you have done enough legwork or homework to fulfill and validate the journey that you are planning to take them on.

I love the fact that you are emphasizing so much the customer and the whys of the customer. This is something that I keep pushing both at the places where I worked as well as with the clients that I consult with, which is the whys of the customer. Simple things like taking the time to go and interview the customer. This is the easy trick, and unfortunately, a lot of folks in marketing and sales miss out, especially in marketing and maybe even product.

When you interview the customer and ask questions like, “What are the objections like or what are your fears when you were looking to buy a product or service?” Another question can be, “How would you explain and define or talk about our product and services to appear in your industry?” Those are something we can use in the copy as well.

Though you might be the company bringing a product to market, it’s not about you. It’s about whom you are bringing it to and making sure that you understand them and speak their language in order for it to make it out of the go-to-market funnel and hit, in my opinion, with the most intentional impact.

Though you might be the company bringing a product to market, it's not about you. It's about who you're bringing it to. Click To Tweet

I love the way how this show got started. A great description and opening. Why don’t you tell a bit about yourself, your journey, both personal and more professional, and what made you arrive at where you are now?

I’m a born and raised native New Yorker. I went to the University of Maryland, and I was a Psychology major. I love people and I love networking and relationships. I was pursuing the path toward child psychology and relationship based. I graduated and what we like to say is I was birthed into programmatic. I remember my first job and I showed up in a suit. I still won’t live that down to this day. It was a site for sore eyes walking into a very casual ad tech company and I was fully professional. As they always say, you can never be overdressed.

I started actually at an ESP-ish-like place CPXi, where I was fresh out of college. I was ready to learn a new industry. I was surrounded by folks that seemed to be hustling and I worked for three account executives covering basically all of North America learning the weeds and getting my feet wet. Following that, I made my way over to PubMatic where I worked with key leaders who all through the years remained mentors and friends. I think this was where I feel I was seen. I learned to grow wings here.

I was given a runway with the sky seemingly as the limit. I came in as an account executive, more junior, and a good portion of the team was out either on maternity or for other reasons. I ended up inheriting a massive book of business very early on and was empowered by those around me to learn, embrace, and succeed.

There were a lot of diverse skillsets teachers. We were like a family back then and I was on the DSP side managing roughly 25% of the entirety of the DSP business. Here, I also learned the balance between the publisher side and the ad solutions team. I started to spearhead the PMP growth and what I call my PMP love story, but the joy of being at the epicenter.

What is PMP?

It’s the Private Marketplace. It is a form of the transaction by the deal, which back then was only hitting the forefront versus where it’s now, which is booming but where I was at the time, I was still sitting on the DSP ad solution side and being able to develop these PMPs, you had to sit in between supply and demand. This is where I think my love of being at the epicenter of that intersection began. From there, I moved to Kargo, a mobile-first SSP at the time that was largely managed when I got there. I was brought there to build their programmatic stack on the business development team.

Here, I got to know the agency and the direct sales teams. I worked alongside their business as a consultant almost and what have you because the goal was to start to transition some managed brands, agencies, and advertisers to programmatic, which was quite a unique experience. It’s hard to get a managed team to want to move dollars to programmatics. That was a learning experience and a challenge, but ultimately, we were able to scale the programmatic business nearly 100% and integrate the programmatic team into the sales org.

Kargo at the time was really a dominant PMP business as well. I was still staying in the line of the private marketplace deals-based transactions. From here, I was brought to TripleLift, and I was brought on to the supply side as the PMP market maker. This was a huge moment for me. I wanted the role so badly. I knew it would be a challenge. I have also never been on supply directly. I was so curious as to how to translate all of my buy side work and working with advertisers and the demand side into a supply strategy.

I spent over a year or so in this position and I wore a bunch of different hats, but I drove the majority of the success for TripleLift PMPs by hustling between supply and demand to build that market and drive revenue. Also, developing custom go-to-market plans for each publisher based on their business models that would suit their commercial teams. You probably are seeing a little bit of a theme here. After some time the epicenter was calling me back and I love TripleLift.

I realized that the buy side was tugging at me and my current boss now, I’m Sonja Kristiansen, the Chief Business Officer of TripleLift, floated the idea of this DSP engagement team in my head. I had approached her to think about what my next path within the company would be, and bells and whistles went off. Now, there was no roadmap. It was, “Here’s what we are thinking, build it. Build something completely new.” I enjoy living in ambiguity. At the time, I had spent and now I moved over and ultimately developed what is now the DSP Global Engagement team. It was born back then and a few years later, it’s a global team of ten supporting big tech teams and additional service model DSPs as consultants.

I love the way you are from an individual contributor in the sales and then moved from demand to supply to being in the epicenter of the marketplace. I love the fact that your psychology background played a big role in all of these things. Would you call that your magic skill or is that the powerful skill that you bring to the table?

What everyone likes to think is so automated, but I always would say I’m old school. What I have learned along the way is relationship-building and being respectful of those that you work with and that a team of teams approaches and collaborating takes a village. I think from my early days in psychology, I love people. I’m very curious. I enjoy learning, asking a lot of questions, and listening to some of the pain points, the gaps, or successes and understanding what’s behind that.

I think that it empowered me to lean on experts around me, and also understand the core functionality of go-to-market, which is what are the needs of the clients? What do they need and how can I help deliver solutions in a way that best suits them, which therefore transactionally would suit us as well as tier-one service partners?

B2B 35 | TripleLift
TripleLift: What are the needs of the clients? What do they need and how can I help deliver solutions in a way that best suits them?


You also mentioned, and this word kept coming up in your overview, which is programmatic. For those of us who are not in the industry, can you give us a quick primer? What is programmatic?

This is always a tough one of what you are going to get. I like to think of programmatic as all of the tech and behind-the-scenes of powering online advertising. To boil an ocean into a really simple phrase, all of the online ads that you might engage with on your phones, on your tablets, or any form of media at this point or channels out of home. In order to get that and deliver that experience to you, the programmatic industry is what powers that. Also, the tech that is involved in doing that and making sure that the right ads are delivered at the right time in more of an automated kind of behind-the-scenes way that you wouldn’t think as second nature shall we say. It’s all the behind-the-scenes work of what it takes to put an ad in front of you as a consumer.

For me, when I’m a marketer or when I’m trying to build an additional marketing campaign, in my mind, I’m an individual and I go directly to LinkedIn or Google or Facebook versus your clients. What you are streamlining is not for this one individual who’s looking for maybe 5 or 10 ads, but we are looking for thousands or even millions and millions of budgets as well.

There is certainly a one-to-one type of relationship between programmatic and reaching those key consumers, but there are larger audiences, one to many. I think that we see that a lot in how media gets transacted these days as well with so many different buying methodologies and even the evolution of how to reach consumers appropriately, how to do it right, but also how to make sure it’s sending the right message from brands to the right people.

I know we can go deeper into this one topic, programmatic, especially with everything that’s going on in the search world, plus the ChatGPT and AI and everything that’s happening. Search is going to evolve for sure, but that’s a huge topic in itself. If you have an opinion, we can spend 5 to 10 seconds or whatever.

I think this is an interesting time for the tech industry. I would say it’s the first time in all of my years in the industry that I think I could say I’m even overwhelmed. It’s so fair to be self-aware. There are so many new players and new media streams. You have retail media that’s now surpassing CTV and new narratives coming out and search and then the deprecation of the cookie, and what have you.

However, what it comes down to is where I was and where things started. You were expected to learn everything and be the expert on all things. I think where we are now, it’s about not only understanding how each of these different modes of media or channels or programs impact your business but also, how are consumers interacting with each of these. Are they overwhelmed?

What does it mean to have a package that hits on all the points of what a consumer is looking for and how can we as programmatic experts or what have you simplify this? How can we digest this when we could barely digest it ourselves? I think it’s so important to stick to the core competencies and principles of what our audiences and what brands are trying to do to reach those consumers and understand those pathways in order to not boil the ocean of the Lumascape these days. Also, make it easier, more seamless, and more efficient for our clients.

This is a huge overhaul and upheaval that’s happening in the industry. Many touchpoints are affecting so many areas across the business models of different tech companies. Not only that, for me as a marketer, I’m challenged to come up with the content and what channels to use for my content now.

We are seeing that, and that’s something that is super important for my team but I always say being nimble. Be flexible. Everyone always wants the same outcome, which is whatever success means to you but the journey to getting there is much more important because you can’t be afraid of delivering a solution that might fail. You can’t be afraid of having something underperform. Instead, you have to do the legwork to understand the goals and what work.

You have to be able to invent and reinvent your own wheel, your own narratives because they are going to change because the ecosystem is changing. Also, new partners are being introduced and it’s exciting, but it’s a consistent hustle where being able to balance that is so important with clear messaging, clarity of goals, and defining the needs in a way that doesn’t feel like they could go in 800 different directions.

With that as a background and context, what I always ask and this will be useful and enlightening for the readers is if you can share a go-to-market success story and a go-to-market failure story. You can pick your choice.

I would say a go-to-market success story is about a few years ago when I launched this team, it was about a year in and social platforms was are booming between TikTok, Facebook, Instagram, Pinterest, and what have you. There are many others. What we were looking at is native at the time. TripleLift is naturally an omnichannel SSP. Native was our core business and we have since evolved it to CTV, OLV, you name it.

Back then, we were working with our key DSP partners to understand how to make natives seem a lot easier. When you say what is native advertising, even when I joined TripleLift, I was like, “What is native?” What am I doing? For people that aren’t familiar with it, it’s ads that match the look and feel of the publisher’s page. That’s what native means to us. However, when you don’t know what it is, you think that there are so many different creatives and overhauls that have to happen.

Instead, what I started to see is the majority of the brands have a social strategy in the market. They have social assets. They are working to generate greater followings on those platforms and they should keep doing that. What I did build was social to native extension. Repurpose your social assets and extend them to native and the programmatic ecosystem.

What this did was it made native easy. It made it efficient. It made it seamless so that anyone in our DSP platform that had buyers that were transacting on social and were working with various teams within an agency could very easily say, “You don’t need to reinvent assets or go through a new creative process.” Instead, here are spec sheets specific to each DSP as to how to take that social video and run native video. Run instream or how to take that standard unit that runs on Facebook or Instagram like a more standard asset and run a beautiful native image ad seamlessly.

The goals prove to be far more successful in a programmatic space than they were in social. Naturally, there are different goals. It’s not discrediting any platforms, but realizing that brands could not reinvent their wheel but extend and grow their share of voice across the programmatic ecosystems and their consumers. It balanced their social strategy well. This was where we got native on the map of an evergreen strategy. The way in which people look at social is the way in which they should look at native and build that without having to do anything all too different than they were already doing.

B2B 35 | TripleLift
TripleLift: The way in which people look at social is the way in which they should look at native and build that without having to do anything all too different than they were already doing.


This was a big success across our book of business. A lot of our key partners looked at us as thought leaders. What was the most impactful for me was I felt like I was able to educate our consumers and our clients. Our clients are not clients that most view as clients. Our clients are DSP internal account teams. Some might say they are a little bit forgotten along the way or the activators, but being able to educate them about what they could do and how they can extend their partnership reach with existing buyers. We saw a tremendous increase as it relates to native adoption, our partnership with each of our key partners, and that they felt supported in this narrative too.

Going back to the early part of the discussion, which is keeping the voice of the customer and understanding that. Also, educating them and bringing them along in the journey. I can see all of those elements or ingredients being played out in this story. Kudos to you.

At least they could say, “I’m tried and true.” I know you had asked about a failure. Along the way, it’s so important to have failures. It’s so important to realize what doesn’t work. I would say that the go-to-market failure that I would address here is when I was back in my first role at TripleLift as the Private Marketplace Market Maker. I tried to develop what I called a prestige PMP package.

The idea here was how can I scale one-to-one PMP to one to many packages for premium publishers. Back then a lot of asks were, “How can I get more premium publishers in one deal with a fixed rate?” I had built this idea of, “Let’s package them together by vertical.” This wasn’t necessarily about performance. This was much more about branding and reach because measuring a lot of publishers at the same time is harder to do back then.

I built these tent-pole and vertical packages. I was so excited about it. I felt that as a one-woman show driving one-to-one PMPs one by one was not going to scale eventually. This I thought was great. This is going to be an easier way to do this. It went to the market and I will never forget it. I was troubleshooting all night with one of our previous co-founders like, “Why isn’t this working” Some publisher is working and one is not. We have the highest win rates but I realized at that moment that I didn’t do enough homework.

It lacked the depth and the research to understand what wrappers are these publishers on and what are agreements we have in place. How do they operate their marketplaces? How is our tech built to support this on behalf of buyers that have different buying strategies? My idea was a little shortsighted and I realized then that I need to take a step back. I’m not done with them yet. They will come back around, but instead, I transitioned it into a commercial piece of, “Tent-poles and vertical alignment for publishers is appealing to our buyers.”

It was the mechanisms of the way in which we were building these deals that I didn’t do enough exploration on. It taught me to say, “What worked,” which was buyers were interested. It was the execution piece that didn’t play out. I shifted that in terms of working with our product marketing team to make it more of a sales enablement play and change the structure of how these deals are constructed.

I will tell you that I’m still not done with them and I hope to come back around to reinvent that vision but I learned from it. You got to go deeper. You have to ask more questions, “What did I miss?” It’s still on my mind and I hope to solve it one day, but at least we were able to become a much more impactful player in the curated deal space in audiences, tent-poles, and vertical but I have yet to crack that code and I will have to go back to it.

I’m sure you must be getting called out for that persistency of yours.

I am persistent. I will give it that. I’m willing to go the distance. I don’t take no very well, but not because I don’t like a no, but because I think a no is one step closer to a yes. Even if I have to burn it down and rebuild it, I am all about finding it. If there’s a will, there’s a way.

This is where I can see your sales mindset coming, which is no, is fine, but no, doesn’t mean never. It just means not right now.

I will come back around and let you know when it works.

It was a great story there. I love the way where you never ever gave up. Again, bringing your sales mindset and thinking to the fore here. Also, something that caught my attention, and again, it goes back to how we define go-to-market, which is yes, you are in a hurry to get that product out. You could see that, but at the same time, you have admitted it after the fact. It happens to all of us, which is we are in a rush and get it done more but then in hindsight, we realized that we missed a critical research piece, especially on sales enablement or how to package or how to portion it for our customers.

Even back then, I was so used to running like a chicken with my head cut off a little bit, but in a singular mindset that when you do bring something to market, there are so many different skillsets and experts that are involved between the product and the deals team for that specific initiative that didn’t go as planned. It taught me to go deeper. Go the distance because you might not have all the answers, but bare minimum, scoping things out and really making sure you do put the time in. Legwork to me is 90% plus of a successful go-to-market.

Legwork is 90% plus of a successful go-to-market. Click To Tweet

With that, as the context and backdrop, how would you define TripleLift’s go-to-market strategy specifically you and your team’s role and function within that?

I will speak to TripleLift first. TripleLift is an omnichannel essential marketplace for better ads that can drive better results. Ultimately, we are an organization that has always cared deeply about consumer experience, client trust, and efficiency. We develop products based on solutions that clients, whether it be advertisers or publishers are looking for or a market need. We deliver them with education and end-to-end support across native display video and CTV.

What it takes for us to typically bring something to market are four phases. There’s the pre-alpha, which is about discovery, understanding competitors, and what the minimum viable product would be to capture market opportunity. It’s a lot of gathering feedback and research inputs. From there, it moves to alpha, which is when product and engineering build the pipes and want to test and test again and verify. Also, understand what’s going on in the environment as it relates to performance, reporting, and basic functionality.

Once it passes that stage, it gets into beta, which is, “Check. We know how it works, but now we want to understand what will drive our customers to buy.” This phase may include a focused beta group of clients, a value test for a hypothesis, scaling out and understanding the audience fit, and understanding the bugs or performance levers that are important to our consumers. Lastly, it moves to GA, which is the official launch where there are training materials, demos, and more. This is when all audiences that are meant to take this to market are enabled and we are ready to sell it at scale.

Where my team comes into play is typically in the beta stage, I would say. To speak about my team, the DSP engagement teams’ services are DSP internal account teams. The account executives, account managers, and biz dev strategists. There are a lot of different titles depending on the organization at large and different divisions. We function as commercial consultants. It’s a layer that very few SSPs if any have because we provide direct service to the hands-on key folks or those that are working with brands and agencies on media planning and the like.

Many forget about these teams at DSPs or look at them as the activators or the pipes, but expect them to handle all the heavy lifting and execution. Whereas, we choose to educate these partners of ours on what our partnership is like with that DSP and TripleLift. What’s enabled, what can they do, and how can we bring them custom materials or custom opportunities solutions that fit the voice of their persona and support them in the market however they need?

Each DSP structure and persona differ. There are a lot of different playbooks and narratives even per product or channel, but we sit almost at the front end of the sales cycle and are typically one of the first teams to bring new solutions to market in that beta stage. What we do is we partner with product marketing to construct or shift narratives that are going to market that best suit our various DSP personas and establish proper positioning.

We understand how this answers the why. Why would this product validate a need in the market for our DSP partners? It allows us to gain feedback on the product, the brand, and the vertical and agency levels depending on the DSP structure through our channel partners. That’s where we sit and how we work with and collaborate so intensely with our internal teams as well as on behalf of our clients in the market.

It sounds like it’s a pretty complex product, and the annual contract value would be in 6, 7, or even 8 figures. That’s a sense I’m getting. Obviously, it’s a complex sales model with a heavy touch and high relationship involved.

I think what’s most important to us is making sure that it’s not about us. Go-to-market is not about you. It’s about whom you are bringing the products to and what matters to them, how that suits their models or possibly solves any gaps, and how that slides in so that it becomes easy and seamless. We are able to then prescribe and walk through end-to-end how to implement a solution in that way.

B2B 35 | TripleLift
TripleLift: Go-to-market is not about you. It’s about who you’re bringing the products to and what matters to them.


Switching gears a bit over here. You did talk about one of your superpowers, which is psychology and sales. Would you give a lot of credit to those in terms of your career growth? How would others or what do others call or tell about you? What is your magic or superpower?

I asked a couple of key mentors and colleagues this question. I figured it was the fairest way to answer it and also where I could get some humor in some responses. Some of the responses were, “Bringing straightforward energy and clarity.” It means speaking the customer’s language and knowing their business as well or better than them. I think this goes back to what we have talked about as legwork. I try to embody those that I’m speaking with, their needs and understand as much as I possibly can about their individual role when taking something to market.

That ties into genuine relationship-building. As I mentioned, I love people. To put it in a quote, “You are incapable of acting or pretending as if you care. You care and you care deeply.” I appreciate that. What was also shared with me is humble confidence and persistent curiosity. I try to be as active as a listener and ask a lot of questions and I’m not afraid to admit what I don’t know to learn more.

It’s being a little bit shameless in nature but those are all core to building proper strategies. This is another good one. “Ali, the bulldog.” Tenacity with charm. The former only works with the latter, but I feel as though the way I would put this is a relentless drive to succeed and empower those around me. I love the hustle. To reference Radical Candor by Kim Scott, move the couches.

I don’t take no very well and I will be ruthless in terms of fixing something that isn’t working or rearranging the furniture, reconstructing a narrative, understanding the why, or burning it down and rebuilding it. I get joy in empowering those around me and succeeding. I love the hustle and that’s so important when you can go the distance and deliver. I’m fortunate enough to be passionate about what I do and work with people that I adore that are mentors and have a great team with me as well.

When you are answering that, I could sense your leadership, your vision, and how you operate. Kudos to you and I am going that extra step to ask that feedback from your mentors and peers and then articulating that so nicely. Talking about mentors, peers, and role models, whom would you credit or whom would you say played a major role in your career success?

It started with my parents. My mom has been a career woman. She was a glass-ceiling girl back in the day in the music industry. She’s always been a mentor to me and as she puts it, walk your walk and talk your talk. My parents have been very supportive of me, even though they can’t quite describe what I do. My mom will pull up my contact card in her phone and read out what I write for her, but she said it’s not updated but they consistently support me and keep me going as well as my fiancé to fuel my drive.

With previous managers and leadership, I have been fortunate enough to work with fantastic people in the space that have also become friends or remain mentors that saw me early on and saw something that I didn’t know I could see at the time. They fed the beast, is the best way to put it. I’m so appreciative of them as a network now and as I continue to learn.

One thing I’m also fortunate with is working for a difficult manager. Someone in my life was in a very difficult situation. I think it’s important to have that because I learned so much. I learned how I would want to manage very differently from them. I learned to be resilient. I learned to speak up and I think that it’s as important. You have to have fumbles along the way, but those that empower you, but also those that maybe want to do the opposite of that and how you can rise above that is as important to me for getting to where you need to be.

A great point about working with difficult managers. When you work with them and it depends on how you define difficult. It’s more that they are not the right or a good manager versus a difficult manager can also be where they push you and don’t take your first solution as the solution.

I would say that I would look at a difficult manager in the way that you described and don’t take the first answer as a great manager. I think that the worst manager is someone that is worried that you would outshine them or as a blocker. That was at a pivotal time in my career where I was fortunate that I had had confidence, experience, and support that allowed me to leverage the previous managers and leadership of I believe you always have to treat people with respect and build people up.

There’s no better thing than recognizing other people for their hard work. Being able to do that and have that support along the way, whether it be personal or work-wise is so valuable. I love to work. I have a work family. I’m fortunate to have a family, family, but it’s all about building relationships and keeping them intact. We are all in this together. It’s the object of this.

There's no better thing than recognizing other people for their hard work. Always treat people with respect and build them up. Click To Tweet

A lot of the variety of topics that we covered so far, started off with how you defined go-to-market and then your career journey so far. We talked about the success and failure stories. We talked about your challenges as well as your superpowers or your magic powers, which is great. One final question for you and the audience love this question. They take a lot of wisdom from this, which is, if you were to turn back the clock and go back to day one of your go-to-market journeys, what advice would you give your younger self?

I support this question. If I could look back, I would say to myself back then, “Keep asking questions. Keep listening. Stay fearless and be curious. The journey has only just begun, but it’s your story to keep telling.” One thing that drives home for me on this is I was in an interview once and I was asked one of those out-of-the-box questions. “If you were part of a car, what would you be?” My response was, “I would be the sunroof.” They said, “Why?” I said, “I feel the sky is the limit.”

Keep asking questions. Keep listening. Stay fearless and be curious. The journey has only just begun, but it's your story to keep telling. Click To Tweet

I was thinking you’d go for the engine or a wheel, but you went for the sunroof.

It was a quick-thinking moment, but it stuck with me. It came out and I was like, “That hits.” I still think, “Keep going. Be curious. Stay on top of what makes you happy.” As I said, be fearless and if there’s a failure, if there’s a misstep, it’s only a failure if you didn’t learn from it.

Thank you for a wonderful conversation. For all your readers, the big takeaway is to be the sunroof and do share. Thank you so much and have a great day.

Thank you so much.


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B2B 34 | Criteo

B2B 34 | Criteo


What does it take to bring a rich experience to consumers as a leading commerce media platform? How does a global technology company help marketers and media owners reach their goal? Get ready to tune in and join Vijay Damojipurapu on today’s show. In this episode, Nola Solomon, The SVP of Go-to-Market at Criteo, shares the value Criteo brings to consumers in the marketplace and how she empowers the sales team and channels. Vijay and Nola also touch on how the business has evolved. Hear more insights as Nola shares more about Criteo. Tune in to this episode now!

Listen to the podcast here


Criteo: Bringing A Richer Experience Through Impactful Advertising With Nola Solomon

Happy 2023 to all of you. This is the first episode in 2023. Here I am. I‘m super excited to receive, welcome, and host yet another go-to-market leader. Welcome to the show, Nola Solomon.

It’s exciting to be here. Thanks for having me.

Im super excited. I‘m sure our audience is excited to hear what you have to share, as well as your journey and story. Your official title is you are the SVP of GotoMarket at Criteo. We will dive into a lot more of your journey and what you do at Criteo. Before we get there, I always have the signature question I ask all my guests. I open the show with this, which our audience love. How do you define go-to-market?

I define go-to-market as thinking about how you bring what is coming out of products into the marketplace so that it starts to bring value to the customers that it’s meant to be for and for the business that is producing it. There’s a lot that goes into bringing something from products out into the market where it becomes usable and revenue-generating. Fundamentally, that’s what go-to-market is structured to do. With all of that comes continuing to have a client-centric mindset with everything so that you can help make sure that the products are the ones that the clients need to solve their problems. It’s informing the product strategy that way.

I love that definition. I love the fact that you start with the product. More often than not, a lot of the go-to-market leaders and people I speak with omit the product. They have the notion that it’s mostly the go-to-market teams, which is mostly sales depending on who you speak with. I love the fact that you started with the product, and then you also mentioned describing the value and what it means to the clients and the customers in the marketplace. The key to it all is how you bring it all together, then enable and empower the sales team and the channels.

That’s a key thing because ultimately, you want to be producing products that a customer wants and needs rather than what you think they want to need. You’re out there in the market trying to sell something that nobody cares about. There is an element of having to always have that client-centric mindset of understanding who your customers are, and what their challenges are, and making sure that the product roadmap is reflective of solving those needs. That makes the job of go-to-market a ton easier when you know that you’re bringing something out that’s much needed. It’s about making sure that the value proposition, the messaging, and the enablement of it are clear. It’s a virtuous cycle when it’s working well.

Your title is the SVP of Go-to-Market. I‘ve not seen this a whole lot. I would also predict that we will start seeing more and more of the official function of the title as go-to-market. How do you describe and why did you push on this title of go-to-market?

It’s funny because my name Nola is also not very common. It’s after Woody Allen’s Match Point movie where Scarlett Johansson’s character is named Nola. I met a lot of Nolas but they’re all very young like kids. I expect a new generation of go-to-market leaders to come up in the industries. The funny thing is that it’s a term that is not well understood by industries. Different companies have different definitions of what go-to-market is and what it means to them.

Go-to-market is thematically the essence of everything that is sales-facing. It’s an actual function to “Isn’t that product marketing,” and a component of product management. What was exciting about my role at Criteo was to come on and create the go-to-market function as a center of excellence and as a bridge between the client solutions organization and the product organization. I’m sitting at the epicenter there to be that layer of both communication but also activation and execution for everything that’s coming out of products and everything that’s coming in from the field.

Similarly, there are a lot of close partnerships with marketing, corporate development, and all of the back-office teams as well at the company. It’s an exciting place to be. Originally, there were pockets of this function at Criteo. There were different teams that lived in different places that were doing pieces of go-to-market. When I started talking to Todd Parsons who was our Chief Product Officer at the time about this role, he was like, “We need someone to come in and think about how we do go-to-market as a function at this company.”

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Criteo: At Criteo, different teams lived in many places and were doing pieces of go-to-market.


That was exciting to me, especially with the fact that with my background, I’ve held a lot of different types of roles that have allowed me to have a 360 view of not only our industry advertising technology but also the different types of functions and roles within a company. I had a clear view of how I would create this.

That’s interesting. The CPO asking you to explicitly build a go-to-market function is cool. I have a lot of other questions specifically on this but let’s backtrack a bit over here. There’s a reason why I want to bring up this question later on. Why don’t you share with our audience about your career journey? You will see where I’m going with this.

I’ll start at the beginning of the AdTech career journey and work my way up. I fell into this industry completely by accident. Anyone who is in AdTech probably has a similar story. It’s a newer industry as well. It’s not something to be learned in school when I was in school. Now, there are classes, and I’m very jealous of those people. After a former life in book publishing, I went on to get my Master’s in London in Child Developmental Psychology. I started working as an ad trafficker at an ad network at the time before programmatic.

It was interesting because I got opened up to the world of AdTech, but I wasn’t super keen on trafficking ads. I was like, “There got to be more fun things to do.” Throughout my career, I was in London for many years. I ended up moving companies from where I was doing the ad operations types roles into doing more business development and account management for publishers throughout the Southern European region and France. I’m half French, so I have the advantage of being able to speak French fluently and sink my teeth on the more publisher sales-facing side and the whole supply side of the industry. In addition to that, programmatic was just starting to blossom.

I was learning what a supply-side platform was as that was becoming something in the space. It was an interesting advantage because it allowed me to understand quite technically how everything works in this very complex ecosystem that we call AdTech. My career then brought me out to Singapore where I spent a couple of years leading the supply team for my company at the time, Millennial Media. We got acquired by AOL. Anyone in the industry who has been in the industry for a while has probably had a stint at AOL.

That was interesting too because it expanded my view beyond Europe to all of APAC. I was traveling around to all the different markets and understanding the different nuances of not just customs but also how businesses operated. That allowed me to think about things from an international perspective, and not a US-centric perspective of “Everything will apply globally.” I ended up coming back to the US after some time in Singapore. I moved into a demand-side platform or a DSP, The Trade Desk, for a role that I was excited about and dig my teeth into the data world.

Everything was becoming clear to me that it was no longer about the ad format itself and only about the content itself. It was also about the audience. The audience is tied in with the data, who are you looking for, and the right user at the right time. It’s that old adage. I got to learn about the data space and all of the different ways that data interconnects in the back end to find the audiences and optimize your campaign so you’re targeting the right moment. You’re able to then measure the impact of your campaign and the ROI.

Learn about the data space and all the different kinds of ways that data interconnects in the backend to find the audiences to optimize your campaign so you're targeting the right moment. Click To Tweet

After that, I ended up running a programmatic revenue team at a hybrid publisher and AdTech company called Dailymotion. That was an interesting role because I had the revenue P&L. We were driving the entire business for the company and about 80% of the revenue. That was a lot of fun in terms of partnerships and thinking about how we keep growing this business.

That brought me eventually to NBCUniversal to lead their programmatic product and strategy under their advanced advertising umbrella, which is moving into broadcast and the CTV world just as streaming was coming up. They were just starting to develop Peacock. I was working on how we enable programmatic advertising there. It was exciting. That was what I was doing when Criteo came knocking.

That’s super interesting and adventurous on your side. You started your career in London and Southern Europe, moved to Singapore, and then came to the US. You‘ve got a very global perspective. I do have a novice question. I‘m more in the B2B world. A lot of the sales happen through sales teams or maybe partnerships and channel members. How does the “sales and revenue gen” happen in the AdTech world?

It’s very similar because it is B2B. A company like Criteo is an advertising technology platform. It’s a SaaS play. It’s selling our technology stack to advertisers and agencies to leverage it to run their media campaigns and do their media buying. We’re dealing with businesses and selling our products to businesses. They’re using our products to then reach consumers to buy their products.

If you go back to your time at NBCUniversal, you were on the other side. Is it the demand side? Is that what you would call it for the ads?

I would call that the supply side. I am now focused on the advertisers and the agencies or those who have the medium or dollars to spend. At NBC and in other parts of my career before, I was on the supply side. I was working with the publishers who have the media inventory to sell. When you go on a website and see an ad, that’s an ad space they’re selling.

I was a novice in the space. Supply and demand are the whole thing now.

It’s the most ubiquitous yet complex thing at the same time.

My exposure is to the OTT world and cord-cutting world. I was at Microsoft as a marketing manager back then for IPTV platforms. One of our big customers back then was AT&T U-verse and others across the world like Deutsche Telekom, Singtel, and Bell Canada. I got to see more on the tech but also to some extent, the content side and how things were changing from cable and satellite to more of IPTV and eventually the cord-cutting.

Now, cord-cutting is mainstream. Five to ten years ago, that was not. It was still early days. It sounds like because of the shift in the business model, all these content producers had to rely on a different revenue stream, which is now the ad space, the programmatic, and the datadriven. If you can talk about that and how the business model has evolved for NBCUniversal and Peacock would be a great example there.

NBCUniversal has always been pretty innovative. They are thinking first and foremost, “How do we continue to be first in all the spaces?” It is an exciting place to be. What was fun about the role there is that they were leaning into programmatic in a way that some of their peer sets weren’t. For instance, there was a great understanding that this was a growing part of the space. At the same time, it was also balancing the reality of this giant broadcasting business.

This is what all of these broadcasters deal with and also publishers in general. They have had a big direct sales business and are used to transacting directly with the advertisers themselves. They were handling IOs and running campaigns on their own in their stacks, and outsourcing this to AI and technology to do it for them with some inputs here and there. Because of the efficiencies that programmatic brought to the space especially for the advertisers, it allowed for a lot of abilities to do things quickly and activate quickly, to measure and create real tactical ROI that could be seen.

That has continued to improve. It’s still a little behind on the CTV side but it’s making huge strides even from a couple of years ago. CTV continues to be a growing space. It became obvious that you have to follow where the money is, but you can’t blindly go there. For somebody as large as NBC and their peer sets, they have to be balancing all of the different ways that they interact with their buyers.

That’s pretty cool given that you’ve had such a diverse set of roles and responsibilities even across geographies. I don’t know if you have kids or not, but on the personal side, how would your parents describe what you do and what your role is?

My dad in particular is funny about it. My parents pretty much get it in the sense that they’re like, “We get that you are helping facilitate the serving of ads to me.” Sometimes I’m like, “That’s an interesting ad. It’s relevant for me.” Other times, I’m like, “I don’t care about that ad. Get it out of my face.” My dad is an author and a writer and was a former journalist. Ultimately, what they both appreciate is that advertising helped keep the internet free. It helps fund editorial publishing.

That’s something he inherently understands from having been a writer in the space but also because he had a digital publishing company in Italy a long time ago. He gets that. I’ll still get emails from them where they’re seeing the news about Meta’s fine in the EU or anything related to Google. They will be like, “Did you see this? This must be important for you.” I’m like, “I saw this last week when it first came out but you’re on the right track.”

I’m sure you must be excited to have a parent like that, and a dad who understands your space and who you can speak with and connect with on several bases. That’s exciting for sure.

It’s nice to be able to have some deeper conversations about what’s happening sometimes.

Coming back to your role at Criteo, can you expand on what your function and responsibilities are, how you are measured, and how you and your team are measured against?

The scope of the function of go-to-market sits as the centralized organization bridging between the client solutions group, which is the sales and revenue-generating group with some support functions, and the product organization. I have four teams within go-to-market that are operating as a unified go-to-market group but each has specialized functions and roles. Let’s call it the product-facing side of my go-to-market group.

I have my product solutions organization. They’re working hand-in-hand with the product managers to make sure that all of the feedback from the field has made its way into the product manager’s ear, and is being considered as part of the development of the product manager’s product strategy. They’re also deeply understanding what’s coming out of the product, what’s being built, how it’s going to get activated, and the value that it’s going to bring in terms of solving the customer’s challenges, and the value it’s going to bring for Criteo as a business.

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Criteo: All of the feedback from the field has made its way into the product manager’s ear as part of the development of the manager’s product strategy.


They’re in charge of building the go-to-market plan, being the experts on that product set, solution set, feature update, or whatever the case may be. Also, being able to articulate, “This is how we’re going to bring this to market. If it’s something brand new, here’s how we’re going to run the POC, the alpha, the beta, and all the way through GA and beyond.” If it’s a feature update and something is in GA but it requires a change of behavior on the sales side or at a customer who’s using a self-service, there’s a go-to-market plan associated there.

How is that different from traditional product marketing? In my mind, that’s typically product marketing and product managers, to some extent, depending on the organization. How is your product solution team different from traditional product marketing?

At a company that’s the scale of Criteo of about 3,000 people, we have a very complex product suite within our commerce media platform. We have four main solutions and then we have these core assets that power them. It’s specialized to get into the nitty-gritty of something. Even as simple as our machine learning algorithms for campaign optimization.

The AI behind that and the number of different tweaks and things that need to be done that bring in the different data, audiences, and all of these things are all product work. Understanding what those are and being able to articulate it into a plan for how it then needs to be activated is where the product solutions team goes.

They’re not focused on, “How do I tell the story? How do I write all of the collateral materials and sales pitch materials?” That’s product marketing. They work very closely with product marketing, which is also within my organization. They’re focused on the storytelling and the narrative, making sure the documentation is there, and also the right type of materials that a salesperson is going to need to be successful in the fields.

It sounds like your product solutions team is a blend of the sales engineer and solutions architect.

I feel the need sometimes to attach other titles to it because it’s not exactly something that’s well-known as a scope. When you’re at a smaller company, you would have either a product manager and a product marketer doing some of that function, or a product marketer doing a lot of it. When you have the scope of the technology detail you have to get into and the amount of planning, organization, and project management that comes with some of these things, they are not necessarily always standing alone. They are intricately involved in some of the other things that are also ongoing.

It’s being able to think about the go-to-market holistically, “What’s our business strategy with this product? What is our goal for this product in terms of what we expect to get out of it?” It’s working with the sales teams or the sales leaders to make sure that we have that business plan and that business strategy attached. That’s where they shine. That’s where I see them being quite differentiated between product management and product marketing. They very much work as a tight trio.

Your first team is the product solutions. Thank you for going and explaining all the nuances and details there.

I do it on a daily basis. The product marketing team is the second group within my team. It’s focused on who are the personas that we are bringing, how we need to show up for them in terms of the narrative, the storytelling, and the materials, what’s the actual documentation on some of the more client-facing collateral on the product itself, and all of those pieces that you would think anybody would need.

They also own, “How do we name our products? How do we keep a centralized repository where everything is accessible and easily findable by a salesperson, and make sure that’s being used and being updated accordingly based upon whether the narrative is resonating or not with customers?” We’re tweaking that. We keep constantly improving. It’s not one-and-done. They’re closely focused on that.

They work a lot with our marketing organization because the marketing team uses a lot of that persona work and the messaging work for growth marketing activation. It’s used for the website. It’s used for the planning that we do between the product solutions group, product marketing, and marketing on press releases. We might want to bring out certain products. Those are tightly working together and understanding both the technical product side of it but more so, “How do you articulate this to this particular customer? How is that different from this customer over here?”

That’s product marketing. You have product solutions and product marketing.

I have a group called Solutions Consultants. This is the group that’s enabling and bringing it out to the market in terms of the actual rolling out. They train the sales teams. They are out there in the field supporting the sales teams and getting pulled into client meetings to help talk about the story and connect the dots with product experts or solution experts. Because of the complexity of our suite, we’re not selling one thing. We’re selling a suite of solutions.

Oftentimes we want to be there on-hand to help support the sales teams post-enablement even. There’s a lot to do in terms of planning the rollout, and getting that rollout and training done of “This is how we could think about bringing these types of products together for this particular customer because of their unique challenge and need,” or what they have told us in meetings. This is largely focused on newer solutions that a salesperson isn’t already well-versed in. The goal is to get everyone well-versed in everything. By that time, we got some new stuff. It’s constantly going on.

The fourth team is my strategic planning and operations group. That’s the group that makes sure that it’s all flowing, and that it’s not a big game where the pieces of the puzzle are connected to roll something out. That’s strategic planning, operations, and project management. That group also works closely with our business stakeholders and all of the other organizations outside go-to-market. We had inputs and outputs for the annual planning for finance, legal, and all the back office teams that need to be alerted and understand how everything is flowing from go-to-market. It impacts their roles in their day-to-day and some of their systems even. It’s making sure the ship is running tightly and we’re not missing the beat on anything.

Thank you for explaining and walking us through the four teams that you have under go-to-market. I would like to shift gears. As you and I and everyone on the audience side know, there are always successes and failures in go-to-market. It’s not just up and up. There will be downs several times. Going back to your time at NBC or at a time that you want to pick, if you can share both a success story on the GTM side as well as a failure, that would be good.

I’ll take both of them for Criteo examples. One of the big successes that we saw and that I’m proud of is the launch of our Commerce Max platform in 2022. It’s our agency DSP. For those who don’t know the terminology, DSP is Demand-Side Platform. It’s the buying technology platform for an agency or a brand to run their media dollars across the open internet.

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Criteo: Demand Side Platform is the buying technology platform for an agency or a brand to run their media dollars across the open internet.


This was a huge accomplishment for Criteo because one of the big areas that have been growing in the space that Criteo has been playing in quite a bit is retail media. Retail media is the monetization of retailers’ inventory on their retail sites, similar to what they have always done in stores with shelves. We’re turning all of that digital with things like sponsored products on display. That has been going on for a few years.

Criteo has built technology to service retailers to be able to monetize their inventories and for agencies to be able to buy these inventories. What hasn’t existed before and something that is deeply needed by the buying side of the industry is the ability to do this while also leveraging a retailer’s unique audiences to find those audiences when they’re not on the retailer’s site. They’re on any website here and there consuming their content. They’re on their phones consuming content. It’s being able to reach them in the right moment to bring them back to the retailer for point of purchase, and then being able to report on that in closed-loop measurement so you can see that drove that point of sale.

That was a huge accomplishment because it helps manage a lot of the fragmentation in this space already that clients need to otherwise use multiple different tools to spend that money in that way. We have brought it into one place for them. That was everything from a go-to-market standpoint. It’s in the market because there was a lot of education and listening to the customers, especially our early partners, in terms of what they need and what are their main pain points and building toward that.

It was an amazing collaboration of all teams at Criteo in products and go-to-market, sales groups, and the customers in terms of building this to what it is now, and then continuing to work with them as they have been hands-on keyboard to be able to continue to iterate and bring that out. I’m proud of what the team accomplished there. That was a huge win for the industry to be able to close the gap on some of these fragmentation challenges.

It sounds like a big win. Congratulations to you and the team there. I’m curious more about the strategic side, plus the tactical side of how you and your team think about the launch. I‘ve seen highperforming teams that define, “Here are the launch goals in terms of PR, customer rollout, wins, sales, pipeline, and so on.What do you and your team think about that?

You always want to start with, “What are we trying to achieve? What does great look like?” That means putting some metrics against it. What are the right KPIs to measure? That depends too on what stage you are in the product life-cycle. It may not even be a revenue KPI yet. At some point, it becomes one. It’s having that established from the very beginning and knowing what you’re working toward. Especially when you’re building something new, you need a test and you’re doing some POCs. You need to know what you’re testing for. What does success look like?

You have to have that defined. Everyone needs to agree on that, including in this case the customer. If we and the client have different definitions of what success looks like for this POC, that’s not going to get us very far. It’s identifying, “Here are all the things we would want. What is the most important 1 or maybe 2 or max 3 that we can work toward, assuming that they’re all manageable in the same breath?”

We start there, and then it’s about making sure that we have the right processes put in place to make sure that all of the different steps along the phasing for all the different teams that are involved are happening. There’s a giant project management component there and regular roll-ups to steer the folks that need to be updated and keep track of whether we’re pacing on track here, and to roll that out.

Do you have a specific launch program management team? Is it the product marketing who is running that?

I do have an enablement function within the go-to-market group. It’s not run and operated by product marketing but they are giant collaborators in all of this because much of the materials are needed there.

That’s a super cool story. Coming back to my earlier discussion and topic, what is the GTM failure story? What are the key lessons from that for you?

Criteo is in its antiquity. It has been around for many years. First and foremost, it was a retargeting company, which was a company that focused on finding you again and again for you to purchase a product. That was enormously successful. They were the first ones to do it. To do that well, you need to be quick, you need a lot of data, and you need to know exactly who you’re targeting and target them with the right thing so that they are more likely to convert. It’s a performance play. That made Criteo extremely successful. You could consider that one product or a point solution.

You need a lot of data to know who you're targeting and target them with the right thing so that they are more likely to convert. So it's a performance play, and that made Criteo extremely successful. Click To Tweet

As Criteo evolved because the space evolved, there was a need to create more solutions. You needed to have more things to sell than just retargeting. Even though we continued to be the best at retargeting in terms of a performance standpoint, other companies also have retargeting products and then other products too. To capture the bigger TAM, there was a need to do that.

We did that but one of the challenges that we faced as we rolled out other products is that we started to have not only what we would call a whole bucket of point solutions like, “Here’s the pitch for when you’re doing retargeting. Here’s the pitch when you’re selling an app campaign, a CTV campaign, or an online video campaign.” All of those were individualized as their sales strategies.

First of all, I created a ton of fragmentation within what we were doing from a go-to-market and sales standpoint. Secondly, as we started to bring those stories together, it also made it difficult for a salesperson to understand “What is the plan when I activate across all of those things?” If we are bringing the point solutions together, you’re not selling videos, retargeting, and CTV separately. You’re selling acquisition or retention to a performance marketer.

They’re either looking to acquire new customers or retain and grow their existing customer base and lifetime value. They can do that through a myriad of different targeting options, inventory assets, channels, and devices. We can offer them all of that through one buying tool. Being able to articulate the fact that we are doing acquisition and retention versus these point solutions was step one. The sales team’s challenge thereafter which became the go-to-market challenge was how we understand how to map all of the different opportunities into the bigger pitch.

That’s where go-to-market sets down and goes, “Here’s how we do these types of plays. Here’s the documentation for these step-by-step,” and how you would think about all of the different types of creatives, whether this creative is more conducive to an acquisition campaign, a retargeting campaign, or a consideration campaign because of the performance and the data that we have in our partnership with products. We were creating a lot of this mapping for the sales teams that then allowed them to be able to bring these stories together holistically. We have seen incredible success and adoption of these materials as well with over 40% growth in our acquisition products. It’s working.

Its funny how this theme continues to happen. It doesn’t matter which industry or what stage of the company you’re in. This is more common in mid to largersized companies where things become siloed. Sales teams do their own pitching. The product teams are doing their own thing. Its like horses pulling in all different directions, which are all targeted and going in one path. It’s cool. Going back to what you shared in your failures and challenges, and coming back to your launch in 2022, that’s a big shift that has happened at Criteo. Kudos to you and your team for making this happen.

Thank you. It’s a lot of hard work from a lot of different folks. It’s an incredible effort.

Doubleclicking on that, what were the friction points or challenges? There had to be an alignment at the leadership level and executive team that needs to happen. It’s not good enough that the alignment happens only at that level. It has to trickle down at all employee stages. How did you work through those challenges?

A lot of what I jumped right into when I started at Criteo was the education piece about shifting away from the point solution mindset to this acquisition retention loop. It’s the virtuous cycle of how that helps form and grow a marketer’s business. First and foremost was how we effectively educate. It’s not because it’s a difficult concept but that’s not how historically we have been selling, and the story they were used to telling or the fact even that there were multiple products to bring together into a holistic story.

We launched what we called the Trailblazer event, which was this huge go-to-market undertaking with tons of content and materials for follow-ups that helped set the stage for what we were doing. It was all about repetition. It was about getting into the markets and having the team sit down, do office hours, go through the materials, and be available for questions until it became ubiquitously part of the everyday language. I joked with my go-to-market team, “The terms acquisition and retention weren’t even being mentioned at all. Now, everyone is saying it all around us.” They’re telling it to us, which is great. You know you’ve succeeded when someone is telling what you said to them back to you.

B2B 34 | Criteo
Criteo: Criteo launched a trailblazer event, a huge go-to-market undertaking with tons of content and materials for follow-ups that helped set the stage for what we were doing.


Did you have to bring in external thought leaders, influencers, consultants, and experts? Was it just the internal team who was doing all this education? A lot of that weight is typically given to a neutral or third party.

We largely did all of it in-house and leaned on the huge effort of the go-to-market team. There were a lot of collaborations with other organizations as well, and a lot of collaboration with the sales leadership team to make sure that they were also very involved and bought into having their leaders and their leaders’ leaders sit in and make sure that was getting digested and disseminated down to the teams. We even did competitions, pitch contests, and all sorts of things to make sure that it continued to land all through the chain.

We’re shifting more to the final segment and the last few questions for you, Nola. What are the key patterns or trends that are on your radar for go-to-market? What’s on your mind? How are you tackling that? Are you tapping into the communities? Do you have peers? How are you tackling all those issues and challenges?

There are a few things. First and foremost, it’s with the scope of the role. Are we achieving and doing everything we need to do to make our sales team successful? That’s critical. We’re continuing to analyze that and improve on that. My partnership with the sales leadership team is incredibly important as well as my leader’s partnership with their peer sets. That continues to be an area that we can always tweak and improve. That’s a big focus for me.

I like to do a lot of research on how other organizations do it, ask around, and listen in because it’s done differently by different companies all over the space. What might work this year may not work next year as our product evolves and as the market evolves. We have to be agile and flexible. One of my favorite things to say to my team is, “We have to create clarity out of ambiguity. That’s our job as go-to-market.” That means being comfortable with ambiguity and constant change.

As the market evolves, we have to be agile and flexible. Click To Tweet

Specifically and personally, do you rely on communities, books, or podcasts? What do you turn to?

All of the above. I’m a huge nerd. I love reading all sorts of things, books, and articles. I love podcasts. I love this show. I have also a lot of business podcasts and writing podcasts I listen to. I find them all very relevant for go-to-market. At the end of the day, go-to-market is a lot of storytelling. It’s a lot about how you position things and how you think about what’s happening in the marketplace, apply it to your business and think about, “What does this mean now? What does this mean in a year? What does this mean in three years?”

I find all of those relevant even if they’re not directly related to go-to-market activities per se. Go-to-market always has to have a pulse on what’s going on in the industry and the space, macro and specific to the industry. There are client meetings and events where you get to sit down and talk with people, whether that’s more informally like this or over dinner or listening to some more formal content that can be educational.

If you were to look back at your career, who are 1, 2, or 3 people that played a key role in your career growth?

It’s more than three people. There are three groups of people. My parents have always been unconditionally supportive and allowed me to galavant all over the world and never told me once to be careful. Secondly, I have had the incredible fortune of having some fantastic managers who have become mentors and friends even both while and after I’ve been working for them. They have helped guide me in my career both in terms of the opportunities I’ve been afforded and also in terms of the thought leadership guidance and partnership of exchanging ideas and debates, which I find so healthy for growth. That’s huge. My husband is also in the industry. He’s more on the technical side. He has been incredibly helpful in continuing to help me dig deep and learn exactly how things work so that I can more effectively talk to people that I don’t know about how they work.

You did it very well in terms of how you covered the three main stakeholders, parents, folks at work, managers, peers, and then at home, husband. The final question for you is this. If you were to turn back time and go back to day one of your GTM careers, what advice would you give to your younger self?

The number one advice I would give myself is to carve out more time to think. I’m hyperproductive. I tend to feel like if I’m not for some reason being as productive as I feel I should be, then I’m not doing anything. Sometimes sitting, thinking, and reflecting is not something earlier in my career that I valued as an actual activity that was moving something forward for me in terms of what I needed to do for my job or my development. Now, I very much understand the importance of taking time to think, absorb, digest, analyze, and then put it to some analytical use toward the job you’re doing or the problem you’re trying to solve.

That could be as simple as reading an article and then taking ten minutes to think about it, having a conversation, and then thinking that through after you’ve finished having the conversation or maybe jotting some notes down. I try to carve that time out now more regularly, which is hard. In some weeks, it’s easier to find some time to do that or not. That’s important because you’re in a constantly evolving space, so you have to be constantly on top of it. That doesn’t mean just reading it and being like, “I knew that happened.” It’s like, “What do you think about what that means?”

Thank you so much for taking the time. It was a wonderful conversation. Good luck to you and your team at Criteo, Nola.

Thank you so much. It’s a lot of fun.


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B2B 33 | Detail-Oriented

B2B 33 | Detail-Oriented


With the prevalence of Zoom and other video meeting programs, it is much harder to remain detail-oriented, take notes, and pay attention to lengthy digital discussions. If you’re struggling with that, Fireflies.ai is your best answer. This AI meeting assistant joins your meetings to take notes, transcribe verbal data, analyze conversations, and a lot more. If you want to rewind and go back to your meetings because you forgot something, you can simply check in with Fireflies.

Join Vijay Damojipurapu as he talks to the Co-founder and CEO of Fireflies.ai, Krish Ramineni. Learn how he implemented NLP technology to create this AI-powered tool. Discover more information about its features and how Krish and his team spread Fireflies through word of mouth and product adoption. Check this episode out so you’ll never miss a single detail on your next meeting ever again!

Listen to the podcast here


Krish Ramineni On Becoming Detail-Oriented On Your Meetings With Fireflies.ai

I have the good fortune of hosting and speaking with Krish Ramineni, who is the Founder of Fireflies. I’m so looking forward to it. Krish is one of those Forbes 30 Under 30. He made it to that list. I’m sure you will be in for a treat as far as good market insights are concerned. With that, Krish, welcome to the show. How are you doing? It’s bright and sunny here in San Francisco Bay Area.

I’m doing great, Vijay. The weather is awesome. I haven’t had a chance to step out myself. This has been quite a busy day. There’s a lot of exciting stuff here at Fireflies that we are working on. I’m doing well. Thanks for asking.

I always start my conversations with each and every guest with this question. How do you define and view go-to-market?

Go-to-market, for me, is about helping people understand that a certain technology, product or service is available but sometimes, even before you talk about the product or service, you have to help them understand if there’s a need or a problem that they are trying to solve. Go-to-market for me starts with awareness and education.

It’s about users’ customers helping themselves acquire a piece of technology or product for their business in the most frictionless way possible. I believe that it’s about letting people buy the way that they want to. The best go-to-market strategies are the ones that are able to take away those barriers and help guide users, buyers or admins through that decision-making process in the most seamless way.

I can see your definition in line with the product-led growth phenomenon that’s taking the go-to-market world and the B2B world by storm of late. There are many flavors of go-to-market. Your definition aligns with product-led growth. I heard you mentioned users and buyers seeing value by themselves and then helping them make the decision where they can take their action, “I see the value, and I’m going to purchase this product.”

There was a time when I was on the extreme end and said, “No salespeople and marketers. It’s only going to be product-led.” The only way you were going to be able to purchase a solution like Fireflies was you are going to see it, try it, buy it, and swipe your credit card. That was going to be the only way. My definition has expanded over time because not every person or buyer follows the same model. Some need more handholding than others. Some have custom requirements.

It’s about understanding the user and what triggers them to make that purchasing decision or that a-ha moment for them. Similarly, when you build a product and are a startup, you are looking for people to get that a-ha moment from the product, saying, “This is great. This is magical. I want to use it.” Even in the buyer’s journey, a lot of times with GTM, people are bombarding you with emails and account-based marketing.

B2B 33 | Detail-Oriented
Detail-Oriented: Go-to-market is about understanding the user and what triggers them to make their purchasing decisions.


Sometimes the SDR function is also part of the go-to-market team. Our first default response now is to say no. We are not even open to the idea, saying, “Why? Yes. I’m curious.” it’s like, “Don’t bother me.” How do you pique someone’s interest and get them to that a-ha moment, whether it’s marketing or from a product lens? At certain times, you can’t do it all with the product. You will need to have people and conversations.

Tell the audience about why you came up with the name Fireflies. What does your company do? Who do you serve?

Fireflies is an AI meeting assistant. It joins your meetings across Zoom and other video-conferencing platforms. It takes notes, transcribes the meeting, analyzes those conversations, and creates a knowledge base for you to search back through. If I want to remember a conversation I had with you where we were talking about GTM, I can search for the word GTM in my conversation with Vijay, and I would be able to pull that information up in a minute. I want to be able to remember all my conversations and also not have to do busy work. Meetings are expensive. We want to help people be more productive during meetings.

B2B 33 | Detail-Oriented
Detail-Oriented: Fireflies.ai is an AI meeting assistant that joins your meetings across Zoom and other video conferencing platforms. It takes notes, transcribes meetings, analyzes conversations, and more.


That was our simple value prop for starting Fireflies. The name Fireflies has an interesting background. My Cofounder, Sam, and I met in college. We worked on various projects. Many of them had nothing to do with B2B SaaS. We worked on drones. One of the things we did was build a drone delivery system. At night when drones fly around dropping packages, they look like Fireflies. We used the name Fireflies and continued using that name for all of our different projects.

Lately, we have had customers come up with their interpretation or story of why we are called Fireflies. One of the things that they came up with, which was very creative, was, “Fireflies is this silent fly on the wall in a meeting that sits and takes notes.” That’s a common idiomatic phrase. Another person said, “Fireflies is very interesting because usually, all of these conversations are hidden and buried after you leave a meeting. Fireflies is lighting up all of these conversations that are happening across an organization.” I give credit to our customers for it but we are running with that narrative for why we are using the name Fireflies.

That’s a very interesting story. The backstory there is around the drone using that in the night, and then you gave the name Fireflies. Something that is popping up when you are sharing those customer stories is that they see value in the product. It’s almost like, “I love the product. How do I give my interpretation or the version of that brand name when I’m using the product?”

Every person has a different way to describe Fireflies. When we get on customer testimonial meetings or interviews, a lot of times, people will see Fireflies in a meeting. When someone asks, “What is that thing you are using?” they will talk about it. They are saying what the solution is. It’s cool to come after hundreds of thousands of conversations.

There are 3 or 4 common ways people describe it to them, “It’s my personal assistant. It’s my note-taker. It helps me stay on top of things.” For our marketing too, let’s use these phrases because almost everyone seems to be using the same theme. Sometimes the best marketing is customer word of mouth. We do see those common things showing up.

The best marketing is customer word of mouth. Click To Tweet

On a lighter note, what is your parents’ interpretation of what you do at work? How do they see that?

For them, it’s about me. Once, I was a Product Manager at Microsoft. I was working at a tech company, going and playing the game of a startup, and trying to be my own boss. That’s something that they see in the early days. A lot of people are like, “Why would you leave a nice comfortable job and do these things?” Over time, they have realized. I’ve even had my dad or other folks who work in tech seeing Fireflies in their meetings at their companies. When people you know, close family, and friends see it, it’s like, “I know this. I know who works on it.” That’s a game-changing feeling. They believe that I’m on a mission to make meetings better. That’s exciting.

There’s nothing like when your parents see and use the product that you are building. That’s an amazing moment in life overall. You also mentioned your career journey so far briefly. You mentioned meeting your cofounder at the university. You went to Microsoft and were a Product Manager. What prompted you to start your company and why around the space?

Going back like most Asian American kids, I thought I wanted to be a doctor in college. I quickly switched over to the engineering side or the technology side of things. While I was doing that, I was never passionate about engineering the same way I was about solving problems, working on projects, and getting groups together. The way I learned to code, how the technology worked, and learned about databases was not in a classroom initially but was working with peers.

In my freshman summer after my first year of college, we worked on an app together, and that idea, “We didn’t have any real internships at that time. Why not make our internship? We need something on our resume.” It turned into this massive tool that we ended up building for college campuses back then. We ended up getting hundreds of other ambassadors to help us market the product. It was a consumer-like product but was great because that was around social media time. It was exciting.

That got me thinking. Most people are using maybe 10% to 20% of the computer science skills that they are working on. There are few companies that are using deep tech or deep machine learning stuff. Technology is truly democratized. Anyone can start working on it. I was never afraid of how difficult a problem was going to be. You just start working on it. I had a lot of fun throughout college. I worked on several other projects. I did hackathons.

The way I met my cofounder he went to MIT. I went to UPenn. We met through mutual friends. My cofounder and I had never met in person for the first two years. We met on a video call. Every evening after our classes or problem sets were done, we would work on different projects and submit them. You win little prize money or awards for submitting to these hackathons. We competed in a lot of hackathons. I remember the first hackathon we won. We got $1,000 or $1,200.

We said, “Let’s take this money and then build some more apps. Maybe we can hire some freelancers to help us market or do other things with it.” That was the entrepreneurial journey. After I graduated college, I ended up graduating a year early. My cofounder was still in school at the time. I went off to Microsoft and learned a lot there. The discipline it takes to build enterprise software is very different. Here we were, kids hacking on a few things.

I got the perspective from both worlds of what it means to be fast, agile, and creative and then what it means to build software that businesses pay a lot of money for. The line is blurred from a technology point of view but from a go-to-market point of view, it’s different. You can take the same cool piece of technology, and someone is going to market it better than someone else. That could be the success point. That was the journey I ended up on. After my time at Microsoft, I reunited with my cofounder. I was there for a summer. I was supposed to go to graduate school but I had a summer off before that.

I went to Boston and stayed there for the summer. We started working on a couple of different ideas like hackathons and then said, “Why don’t we start a business, work on this for a few years, and see where it goes? We are not going to get an opportunity like this later on.” One thing led to another. We moved to San Francisco and incorporated the business. We went through 4 or 5 pivots and then landed on the voice space. That is the current version of Fireflies as it is.

Some of the traits or some of the stories that I’ve seen with successful founders is that they started working on a problem that they connected with. That turned into a startup. Was there a story around that for you and your Cofounder, Sam, where it was around recording transcription? “This is the new and emerging space. Let’s figure out and use AI to do something about it.” What is your thought process like?

It was a combination of both. We were fascinated by NLP technology. Everything we built early on was around how we understand text and conversations and help people be more effective. Honestly, our very first idea was, “I get 5,000 emails every day at Microsoft. Let’s build a tool that tells me which emails I need to prioritize.” It’s almost like Google PageRank for emails. For that, you understand what’s in the emails and rank it.

It’s a nifty productivity problem but maybe not a problem that someone is going to pay a lot of money for. That started as the initial project that we were thinking about, “How do I save more time because I can’t deal with emails?” A lot of people were out there building a brand-new emailing system. Our goal was not to build a new system but, “How do we take something that’s there and make it better or add new technology to it?”

Another idea we had in our journey for pivots and iterations is that I tend to do a lot of messaging over LinkedIn and different chat apps. I can’t remember all the promises I make to people. I use a bunch of different to-do lists but it’s very hard to keep track of who I’m talking to and what I’m saying. We built a Chrome extension that would track all the conversations I’m having with different people across different apps like Facebook Messenger, WhatsApp, Slack, and all these different apps.

Anytime I made a promise to someone saying, “I will send you the report next Friday. Let’s meet up next month,” it would automatically detect that using NLP and create a to-do list for me, “Here are all the tasks or promises you’ve made.” If someone promised to do something for me, it would also make all the tasks, pull out the dates and times, and set up automatic reminders for me.

If I had a chance to go and work on this project, I would because it’s fascinating. We even applied to YC with it. We got an interview day. It was an exciting project. However, for us, it’s a GTM thing like, “How do you now take this productivity prosumer-type tool and sell it to businesses or B2B? How do you make money on this? How do you monetize it?” That was a real challenge.

That’s why we took a pause on it but we took the same technology and learning and said, “There’s this huge blue ocean in terms of meetings.” For emails, I can at least go back and look at an email I sent two years ago. I can look at a chat message I sent two months ago but once I leave that meeting room with Vijay, I probably will not remember for one week what I discussed. I will not be able to recall that memory, “Let’s build a knowledge base of all of my meeting conversations and then run this NLP that shows me action items, dates, next steps, timelines, and deadlines.” That became what Fireflies is.

There are a lot of things to digest over there. You mentioned product-led growth. You gravitated toward product-led growth from the early days. Is it fair to say that you added on a sales-led motion more recently after product-led growth?

We are working on the sales-led motion as we speak. The way we look at our sales team is that we call them customer onboarding managers. We believe that as people come in, they are aware of the technology or interested in the technology. How can we help guide them through that process? What you would see typically in pre-sales is a fusion of customer success and sales because many of them are not starting from zero. They are starting with some knowledge of the platform.

We found that there are certain types of customers that need to turn on specific integrations or they have specific questions that they won’t be able to get answers to in the self-service. The majority of our customers, whether it’s a 1-person team or a 5,000-person team, can theoretically sign up, add teammates, build-out, and pay for it at a large org level without ever talking to sales.

I believe in the Atlassian go-to-market model. Zapier has a fantastic go-to-market model. Calendly had a fantastic go-to-market model. However, when we are building collaboration software, there are going to be different things that we need to go through. People have security questions. They want to know about our compliance stuff. We do a lot of work there as well. We want to be an enterprise-grade product that can be as easy to purchase and use as a consumer product.

Somewhere along the way, you realize that you need people there for those that need help. It’s less about us spamming people with emails and doing outbound. It’s more about how we build that inbound funnel and use the product-led leads. Maybe if there’s someone that is at the right stage to potentially purchase or upgrade, and they are from a high-value account, we should probably give them more attention and more of a white glove service. That’s where we have the salespeople.

Selling is less about spamming people with emails and more about building an inbound funnel. Click To Tweet

There are two tracks that come to my mind. I would love to dig deeper into both tracks. The first is with PLG. It’s all about how can your target users find your product and self-onboard and how quickly can they see the value. It’s all about that. That’s one component. The adjacent component and critical part is the virality because that will reduce the CAC for you. At the same time, it shapes or translates to growth on its own. That’s the first track. Keep that in mind.

The second track is the PQLs or Product-Qualified Leads, which is the sales assist model you are talking about. Let’s deep dive into the first track. In theory, it all sounds wonderful. I was brought in to build a PLG at a Series B startup. We went down that path but it’s super hard. In theory, it boils into three steps. One is how you get users to find the product. The second is self-onboarding. The third is finding value and virality. Those are the 3 or 4 steps in theory. It’s easy but it’s hard to execute in the real world. Help the readers understand the challenges that you ran into early on. How did you work around those?

We were able to build a critical mass of initial users that were able to bring Fireflies to more meetings. That was the triggering point for virality. I will start with the first point, self-service. A lot of people can even experience Fireflies before they even sign up. They can see the bot in the meeting. They will have a conversation. Word of mouth is probably our number one thing. People talk about it. Firefly sends a meeting recap afterward the meeting to the people.

When it does that, they are able to view the transcript and the notes. They are like, “This is great.” We have a thing saying, “Sign up and start using it.” That’s where we get most of our growth. We don’t spend money on other channels like advertising or ads. It’s word of mouth and direct search traffic. It’s a result of word of mouth or seeing it in a meeting and saying, “What is Fireflies.ai?” Luckily, our domain name is the same as our company name. People tend to see that and talk about it.

We had a customer of ours who said, “I saw more Fireflies than I sell my SaaS software because I talk about it so often,” which is fantastic. A lot of times, people are going to be able to see and use it. We now have a free trial as well as a freemium function for the product. You get full access to freemium, where you have limited transcription, credits, and storage. Usually, people will hit certain paywalls and decide to convert on their own or go through the full free trial, get a lot of questions answered, and convert that way.

Through this process, we will also see some people who are like, “I see this. I want to sign up for it but before I sign up, I need to think about how I deploy this to an org. I need more of those IT-level questions answered.” They will request a demo. Usually, when we ask them, “How did you hear about it?” it’s like, “So-and-so told me. I saw it at a meeting. I’ve heard about this. This is exciting. I want to check it out for myself and see it to believe it.” That’s the motion.

We also have PLG. This is probably still the hardest one. A lot of people put very interesting flavors on PLG, “You are going to have a customer. They are going to respond back to you.” To be honest, many PLG people don’t want to talk, “Let me buy on my own. Don’t bother me. I might buy it for myself or a few folks but I’m not going to go and do an org-wide deployment. You are talking to the wrong person. I’m not the person that’s going to buy for my entire org.”

B2B 33 | Detail-Oriented
Detail-Oriented: Many product-led growth people don’t want to talk. They just want to buy something for themselves and will not do an org-wide deployment.


For PLG, you can do all the work but you have to not bother the wrong type of users. Maybe as you have people inside a particular domain start using it, you start doing org mapping. You have to do traditional account-based marketing. We are still figuring that out. That’s hard even for Series B, Series C, and later-stage companies. It’s not as easy as it is for other companies or how other companies make it seem.

I’m sure even for Slack, who are some of the greatest proponents of PLG, it took a long time for them to map out, “There’s a small group of people in this company using Slack. How do I get their IT admin to deploy Slack to everyone?” That’s a sales challenge on its own. PLG can give you leads but that doesn’t necessarily mean those leads are going to be the decision-makers in an enterprise org.

Product-led growth can give you a lead. But that doesn't mean those leads are going to be the decision-makers in an enterprise. Click To Tweet

That’s where I do think there is a fundamental challenge. It’s not as easy as investors or other people make it out to be, “PLG is beautiful. It reduces your CAC. You are going to get all this.” One thing we have done well is self-service and the revenue we get from users’ businesses that way but to do enterprise-wide deployments, selling the department is one challenge. Selling to an enterprise org that’s where maybe you will need a sales GTM function. The PLG is a way for you to show them, “We have an in. There’s some value here,” but you still need to have effective ways to have those conversations.

This is a good segue because I ask each and every guest of ours or whoever comes on the show for them to share a GTM success story and a GTM failure story. It’s your choice. You can pick either a success or a failure. I would love to get your thoughts and personal experiences from those.

There are general ones I’ve talked about where we have seen the virality work, and these things work. With GTM failure, there are a lot of enterprise-based companies. They will put fancy names on the existing technology and say, “This is insights. This is going to tell you all of this stuff.” They will take the core technology features and functionality and put layers of stuff. They will call it revenue intelligence, deal intelligence or some of these fancy words for basic stuff like analytics.

What we have found is that it works when you have salespeople selling and selling that sauce but it doesn’t work when you have a self-service PLG motion where people are like, “Say what it is and how it works. I don’t want you to use crazy acronyms or special words.” That works when you have a great sales team, and you can sell on the narrative but we found that it’s much more effective to be able to say exactly what the technology does and simplify what you can do with that technology and the basic features. That has a way more success rate for us at the type of customers we are targeting at the PLG level.

We try to do traditional B2B marketing where you will go through the entire website and a few pages, and you are like, “I don’t even know what their product is.” They are promising all these benefits and then saying, “Talk to sales,” but I have no idea what this product is. When we tried some of those experiments in the early days, it was not effective. It didn’t pique people’s curiosity as much as, “Let me show you, not tell you.” That was something I noticed.

If you can share the success story and the early days of Fireflies, that would be great.

2019 was when we first started working on the alpha version of Fireflies. Later at the end of 2019, we raised our first seed round and then kept working. We got into the beta. We did a broader rollout in January 2020. A few months later, the pandemic happened. All hell broke loose. It was crazy. These technologies were becoming more front and center. Everyone was spending time on video conferencing. We built Fireflies for a world where it was going to be hybrid for in-person as well as remote. If it’s in person, it would join through a conference line.

We built it for that world but everyone went to video conferencing. We are this fledgling startup. This is starting to pick up and take off. We have to build the platform for scale. You can’t glue things together. We were fortunate after our seed round in the last couple of months of 2019 to rebuild our entire architecture from scratch. Otherwise, we wouldn’t have been able to handle the incoming demand that was coming in 2020. We kept scaling up.

Before you go to scaling up, how did you get the word out that there’s this product named Fireflies? Who was the initial audience?

We launched to a handful of folks in our network, our friends, and maybe 200 people. We had a waitlist of a couple of thousand people. We didn’t have this million-person waitlist like some of these other companies. Those people were originally the drivers. There was zero spending on marketing. In the early days, we gave a lot upfront of transcription credits and stuff. We encouraged people to share Fireflies. There was also that word of mouth and showing up in meetings.

Did you send out emails, drive people to a landing page, and say, “I’m interested. Add me to the waiting list?” Is that how it does?

We had a ranked waitlist where if you share with more friends, you go up the waitlist. We tried that strategy as well. We did product hunts. We did a lot of outreach, launches, and relaunches. Every time we had a new video conferencing platform, we supported it, “We now support Zoom. We are now supporting Google Meet.” We would do an announcement about that. There were a lot of announcements for new things that we did when we had a new CRM integration.

Every integration connection was a new announcement. Every integration we built was an announcement. We knew that this was starting to work when other people started to bring their Fireflies into meetings with us. You start to see it full circle. We could track in the early days when we had our initial customers here in San Francisco, California Bay Area. They would have a meeting with a customer in Atlanta, Georgia. We said, “Why are we blowing up in Atlanta, Georgia? Why are there so many other companies using it?”

Those people brought it back to people in the Pacific, Northwest, and Seattle. That person brought it back to the original user, which was in San Francisco, California. We started to see that flywheel. It’s a firefly hopping around the map. That was something that we thought was very cool. It sounds like there’s some crazy magical thing that we had to do but we built virality into the product. We incentivized sharing and people to talk about Fireflies and share the recaps and all of that.

B2B 33 | Detail-Oriented
Detail-Oriented: Fireflies.ai built virality into their product. They incentivized people to talk and share stories about it. They never charged anyone in 2020 thanks to product adoption.


Was it a freemium or a free trial?

Initially, in a good part of 2020, we didn’t even charge. Until we started seeing traction, we didn’t even charge for the product.

For the entire duration of 2020, it was all about product adoption.

For the greater part of 2020, it was all about product adoption. It was only in the later part of 2020 that we started monetizing.

Can you share some stories about the pricing? What did you think about the pricing? Who were the initial set of folks you would go to pitch and test the pricing? What is that like?

There were a couple of suggestions from folks and advice that other people gave. One was, “Go to enterprises or mid-market, charge $20,000 to $30,000, and sell it like a sweet solution.” We didn’t feel like that would fit with our model. It’s a great way to get quick revenue but you are going to tap out after 10 to 20 deals. You are going to have to hire more salespeople and do all of that.

The best advice they say is, “Close a bunch of deals yourself,” which I’ve done before we hired other comms people but that is if you are doing a sales-led company. Instead, we said, “Success is going to be if we can get to some amount of revenue where we never even have to talk to the person, and they are purchasing on their own. That is success for us. That is the Holy Grail or North Star for our SaaS.”

Success is getting revenue without even having to talk to a customer to buy your product. Click To Tweet

We started looking at different pricing options. One was, “Do we price by utility? How much do you use it?” We realized a lot of people don’t want to worry so much about transcription, “I can’t use it in these many meetings or that many meetings.” We don’t want it to feel like AWS because AWS is great for developer products but it’s not great if you are buying SaaS solutions.

People want à la carte, “I buy ones. I can consume as much as I want. I want a buffet.” We were one of the first people in the industry to do that, and we made it unlimited usage. You can pay one price per seat. We started experimenting with seats. Initially, there were a lot of individuals paying for Fireflies. Over time, we said, “Fireflies is great as an individual product but how can we make it even better as a team product and a multiplayer product?” We realized there’s a lot of value in creating a team product.

Even Calendly, in the early days, was a single-player product. For the most part, it is a single-player product but they have come up with some creative ways or added certain things. A lot of times, for many companies, a multiplayer product has admin controls, admin access, admin safeguards, and stuff like that. For us, there’s inherent value if you have a workspace with your sales meetings, teammate sales meetings, and HR meetings all in one central place. We are building a living, breathing, and self-updating knowledge base or workspace. That is magical.

I’m looking at your pricing page. It was $0. It’s free forever. You have Pro, which is $10 per seat per month. The Business is $19 per seat per month. Was this the price that you launched with? Was this something that you iterated? Clearly, it has to be the second one. How did it evolve to this?

Surprisingly, this is the pricing we started with. We got lucky there. We had a gut instinct. There are a lot of people that say, “Why are you making it so affordable when your competitors are charging $100, $200 or $120 per seat?” I know some of the competitors in the revenue intelligence space. I wouldn’t say competitors because we also focus on a diverse set of personas. We are not just sales. We want every person inside an organization to use it. They are charging $120 per seat. Plus, they have an implementation fee. You must pay $10,000 to $20,000 to get the platform set up.

Why are you not charging that level when you are offering powerful technology that’s 90% of everything that’s there, plus some other stuff? We had in the early days four tiers. That’s one thing I do remember. Early, we had 4 tiers and simplified it down to 3 tiers. The other tier was where it was an audio-only tier where you got more storage but then we realized, “Let’s keep it to three tiers and make it available.” It was easier for people to decide.

How would you define your ICP? How did that evolve from day one?

This is the hard part because we have many different personas and industries. If you were to ask Dropbox or Calendly what their ICP is, it’s very difficult or even Zoom, for that matter. We believe our general umbrella is that any knowledge worker that has meetings in the corporate space is very important to us. There are different types of meetings. There are internal meetings like operational meetings that you have. There are customer-client-facing meetings. You have candidate-based meetings. I look at it as the four Cs. Your Customers, Candidates, and Colleagues all form your Company.

B2B 33 | Detail-Oriented
Detail-Oriented: There are different types of meetings, and Fireflies.ai helps you capture and build a knowledge base around them.


That’s how I think about it. In any conversation that’s happening, the voice of your organization is what Fireflies is helping you capture and build a knowledge base around. Instead of comparing to other AI tools out there, let’s look at what great knowledge management tools of the past were and now are. You look at SharePoint. Every enterprise has SharePoint. It was a fantastic tool back then. You have other wiki software. Atlassian has its wiki software.

There are so many of these different wiki software but the problem is whether I’m using Google Docs, Google Drive or Dropbox, all those documents will end up getting stale if I don’t update them. If someone is not updating those articles or help desk stuff. Whereas with Fireflies, every conversation is automatically updating your knowledge base. I don’t have to manually update it.

Years ago, we had a very different conversation about pricing and how we should charge customers. After all our learnings, we have another thought process around pricing and how we should charge. If a new person is hired, and we never updated that knowledge base from years ago, they are going to onboard with the wrong mindset. That is very expensive to untrain and retrain, whereas if they are using Fireflies, they now are able to get up to speed.

We also use Fireflies almost as an LMS where when we have new people that are onboarded, we say, “Listen to these Fireflies recaps on our best sales calls. Listen to these on what to ask the candidate when you are interviewing them. If you are a first-time manager, this is what you should be asking for. This is why we made an important architectural decision. You asked about why we are using this technology. You are getting onboarded into the code base, so go ahead and take a look at all of this stuff.” I don’t have to ever repeat myself. I say it once. It’s equivalent to me saying it a thousand times in a way, which is funny. That’s the one thing that helps all of our teammates.

That’s a very interesting use case. Typically, when we talk about recording meetings, it’s mostly in the context of customer sales and sales coaching but what I’m hearing based on what you are sharing here is that it’s almost like an internal LMS or Learning Management System. These meetings happened. As an example, I want to understand why the scaling and architecture changed. I type that in, and it’s all there versus having to talk to people or even worse, not knowing who to talk to in the first place.

The best part is that we want you to be able to consume that data without having to sit and listen to the entire 30-minute or 40-minute meeting. You can look for the word integration or architecture, jump to that point in the call, and listen to that snippet or soundbite. If I had great feedback or customer input that came in through this meeting, I will highlight that 30-second clip created into a soundbite and share it with the team. How can we help you consume and get knowledge in 5 minutes instead of 50 minutes of listening to that call or reading a 50-page transcript?

It looks like you got that early traction. You are looking to scale. What are the different channels? For PLG, some of the popular channels are virality, word of mouth, referral, organic, inbound, SEO, and even paid. These are the popular channels or even affiliates. I’ve seen affiliates also coming up on the charts now. What are the channels that you are excited about and something you are exploring as you scale?

We are exploring other channels like affiliate and referral marketing because a lot of these people are saying, “I’m already referring Fireflies to so many people. Can you have some incentive where I get more transcription credits or get paid for that?” We are exploring that. This is coming from user-generated interests. We never had an idea of doing this but there are a lot of people that are willing to advocate and push Fireflies. We want to be able to push that.

There are people creating content about Fireflies. When I go on Twitter, they are like, “Here are the five best tools that I use for AI that help me be super productive.” They list Fireflies. How can we streamline and supercharge the customer conversations, the customer voice, and what customers are saying? One of the things we are exploring and still learning about is how we set up a great referral program for existing users that refer other users and then how we set up a great affiliate program for people that want to drive traffic to our website or convert and then get paid to do that.

I always believe that could be a great strategy. We also see interest from consulting firms and other types of folks that want to implement a solution like Fireflies at larger organizations. That has been less of our focus because we want to go direct to our customers but it is also something that we could potentially explore in the future.

We are coming up against time here. In the last part of this interview, I would like to get your thoughts on what resources you lean on. Do you have a network of founders, a network of advisors, podcasts or books? What resources do you lean on? For example, we talked about new channels for scaling. How do you figure that out? What’s your process?

I like to look at what the best companies have done, what lessons they have learned along the way, and what works for them. I have to assess, “Is that right for me, our business, and our ACV?” I don’t like to look at what’s trending as a word. This is very common in the early days when advisors or even when we go out to fundraise. A VC will say, “Have you heard about this? You should try it out,” without having any context of what it is or how it works. We are fortunate to have great VCs that are part of our board and are able to think thoughtfully about what it is that we need to build that is relevant to our business and filter out all the white noise that’s around.

I like to look at what the best people in those companies have done and the takeaways we can learn from them. I also read a lot. There’s a huge community around PLG of companies that are talking, “Here’s what we have done. Here’s what works. Here’s my Substack, my podcast, and my YouTube video.” For all other things GTM and beyond, SaaStr is a fantastic community. They help us think a lot about benchmarks, metrics, what VCs look for, and what metrics we should track ourselves against. There are a lot of great folks out there that are providing insightful content.

Look at some of the best companies and what they've done. Take away what you can learn from them. Click To Tweet

David Sacks used to have a lot of great SaaS stuff on how you build a SaaS operating system. How do you build that machine? If you can get people that have done it from a reputable source where it’s a similar business or maybe it’s a PLG, a similar price point, or value-add type of product, it’s much more relatable. I’m not going to look at a company that does $200,000 ACV average deal sizes and how they do webinars. That would be cool for us to figure out but I would want to look at how a company that does one-to-many customer success or webinars that is of our size, price point, and type of industry.

If you have to look back at your career, who are those 1, 2 or 3 people that played a pivoted role, either mentor, sponsors, or role models?

Jason Lemkin had a profound impact on everything we do, especially when we were new to SaaS. He’s the godfather of SaaS in terms of helping founders learn about the community. He’s fantastic. I’ve said it many times before. There are some exceptional disciplined founders that I look up to that have gone the atypical path where they don’t raise crazy amounts of money. They are very disciplined. They had humble beginnings like the CEO of Calendly and the CEO of Zapier.

We have Expensify. A lot of these companies have built these monster giants without having to raise capital or spend unnecessarily. They are intentional. Atlassian is something I brought up. They had a very aggressive model back in the day where there were no salespeople at all but they have a similar notion of sales where it’s more of an advanced form of customer success that helps upsell and get in. They used a lot of resellers to help deploy Atlassian products.

I look at those folks and say, “Especially in a market where we are heading into a downturn or a potential recession and where capital is drying up, how do you be the most disciplined company out there? How can you learn from that?” Growth is fantastic. Growth is important. Growth at all costs only works when capital is infinite. When you don’t, we are going to start seeing more people adopt PLG and these other methodologies in 2023.

Growth at all costs only works when capital is infinite. Click To Tweet

Personally, I’m not a big fan of growth at all costs because that will drive bad habits across the board and the GTM teams. I’m just sharing my thoughts. It’s pretty amazing and inspiring that you are focused on how you grow in a very disciplined manner without raising a lot of funds externally. The final question for you is this. If you were to turn back time and go back to day one of your journeys, what advice would you give your younger self?

Persist with an idea until a certain point of failure. What I mean by that is people say, “Throw 1,000 different ideas at a wall and see what sticks,” but to make an impact, if you have a wall and you are trying to hammer and break that wall down, you are not going to hammer it at 1,000 different places. You are going to pick one point and keep drilling until it cracks open. This is another way of saying, “Focus matters.” You want to pick that area and keep chipping. Instead of 1,000 hits, you only need to do 100 to break through.

Ideas are great. Throwing a lot of things on the board is great but if you do too many at once or have too many ideas, conversations, and different things, you will get distracted very easily. You won’t be able to find a breakthrough or where the gold was initially. I talked about that Chrome extension I built or the email tool. If we went deeper, we would have probably gotten to a point where we said, “We can build a business around this.”

That mindset is important for founders because it’s not going to happen in 12 months or 24 months. It’s going to take time. If you see anyone out there who went from 0 to a unicorn in 12 months, you must also ask yourself, “How defensible is that? If it’s that easy for them to build a $1 billion business in twelve months, is there a defensible moat?” To be honest, for most startups, it’s going to be very difficult and painstaking. You have to be willing to go through that grind.

I mentioned that was the last question but I have a follow-up question based on what you answered here. Focus is important but something that I’ve seen especially in the GTM teams and when you are scaling, is this. How do you figure out where to focus? You mentioned the different channels. How do you know which channel to focus on? Early on, I’ve heard people saying this, and something that I’ve seen is, “Place and do multiple experiments at the same time and then pick which one to focus on.” Would you agree with that? Do you have a different view there?

If you have the resources, do it, but most small companies won’t have those many resources. I would rather pick one, fail fast, and then move on to the next one. I found more success instead of parallel processing to go single-threaded and go very deep. Have a metric you want to hit, an amount of traffic you want to drive, or a number of signups you want to try. Set yourself an idea, “I’m going to run ten experiments here. I’m going to do this in this period.”

We struggle with this as well all the time. Sometimes you want to chase shiny objects. If I run 2 experiments on 10 different ideas, it may be less valuable than running 10 experiments on 1 idea, failing within 1 month, 2 months or 3 months, and then going on to the next thing. I would rather go all in and invest in that. If it doesn’t work, I will go to another one. If you have a lot of resources and have four-person teams that you can run on different things, you can do that as well. Neither is a wrong answer. One is going to be more expensive than the other. That’s all.

Thank you so much for your time. It was a wonderful conversation. I’m wishing you and the Fireflies team the very best.

Thank you so much, Vijay. I had a great time as well.


Important Links


About Krish Ramineni

B2B 33 | Detail-OrientedI love building and scaling products/platforms/APIs that simplify the way people work. Deeply invested in Voice AI, RPA, and enterprise workflow software.

At Fireflies.ai, we’re automating work from meetings. Actively hiring across product, engineering, sales, and marketing.

Gartner’s Top 25 Enterprise Software Startups. Featured on the cover of Entrepreneur Magazine: 12 Founders Changing Business 2020.


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B2B 32 | Sales Forecasting

B2B 32 | Sales Forecasting


The biggest skill you need to learn when entering the market is sales forecasting. Knowing and hitting your numbers is an important ability to possess, especially as a sales leader. You need to have the right methodologies and processes in place to achieve the highest levels of market success. This is where the company Clari excels at. They help go-to-market orgs overhaul and run their ultimate revenue processes.


Join Vijay Damojipurapu as he talks to the SVP – Global Head of Sales at Clari, Holly Procter. Learn more about her career journey before she got into this company and what she is doing now to support go-to-market orgs across the country.

Listen to the podcast here


Sales Forecasting As A Go-To-Market Org With Holly Procter

In this episode, I have with me Holly Procter, who is the SVP and Global Sales Leader at Clari. For those who have been avid readers of the show, this is the 2nd or even 3rd speaker from Clari. Again, no affiliation or anything. It happens somehow by luck, faith or whatever you call it. We do have a series of speakers coming in from Clari but all in all, you will be in for a treat. Welcome to the show, Holly.

Thank you so much for having me. We appreciate your bias for Clarians. I will try to do my best even though you’ve had some good nuggets from other Clarians too.

As with every guest, I start my show with the key question that’s top of mind for all the readers, which is, how do you define go-to-market?

When everyone thinks about go-to-market, they start with the basics of how you sell your product. You sell your product through generally a handful of channels. That would be inclusive of both partners and also your direct sales team. Over the years, we’ve certainly expanded our view of go-to-market to include pretty much anyone that might touch revenue.

B2B 32 | Sales Forecasting
Sales Forecasting: Go-to-market is not just how to sell a product. It’s anyone that might touch revenue. It includes everyone from your revenue development teams to your content teams.


At Clari, I think about our go-to-market teams in our tip of the spear, what we call revenue development, which is our SDR function. Even before you get to RevDev, we think about the funnel. You are thinking about all marketers. You are thinking about content teams and people that might engage with your audience, even if that audience is not an active prospect or customer success. We have a deep sales engineering team and even post-sales, so people are responsible for implementation services. Anyone that touches revenue, which is any pre-customer and post-customer experience, we define as part of our core go-to-market team.

That’s more expansive than what I’ve heard from others. Not from my show guest specifically but from others in the industry. Again, you can clearly make out the provision that they like by asking this question. What I’ve seen is that folks who are in sales think go-to-market is sales and nothing else. Folks who are in marketing, and especially those who are in product marketing, think they own go-to-market but lo and behold, sorry, you are in for a rude shock. You clearly don’t own product marketing. Customer success, I’ve seen off late the connotation shifting to include customer success, which is good. One gap that I saw in your definition or your perspective, Holly, is how come you left out the product.

It’s a great point. I love our product leaders. If they are reading, I hope that they will take my apology. The product is massive. What I would say, and part of the reason why I didn’t include them, is that we probably haven’t yet figured out how to crack the code on incorporating them as a close loop in our process and how they play a role in touching the customer experience outside of building a great product but no question. That informs everything we do. I will give you an active example.

We are now going through planning for 2023, as most companies are. A big part of our planning process is figuring out what product features we are going to announce and launch in 2023. That will deeply inform how much and how many accounts I can assign based on what new open accounts we might unlock in line with the product roadmap functionality. It’s such a core part of the way that we build the business and product go-to-market.

That’s the thought process. That’s what I’m seeing. That’s a shift happening in the industry, which is product also becoming a core part of the go-to-market. Even within the product or outside of the product, there is a design that has a big impact on user experience that translates to the sales and how quickly you can go close and customer acquisition costs, and so on.

Anyway, enough rant on the go-to-market piece. I would love to hear your story. What has been your journey? I’ve looked at your LinkedIn profile. You had a very blessed career and a very interesting career path. You started off as an employee at the university you graduated from, then now you are the Global Sales Leader at Clari. Walk us and our readers through that journey.

I’m from Nebraska, originally. I got both my undergraduate and graduate degrees from Nebraska and then decided to work for the university under the guides that we had an asset that was a facility. We were trying to figure out how to monetize this facility. It was this huge rec facility, and we were trying to figure out if there was a path to monetizing both access to the asset and the building. Also, what else did we have?

We had access to a population of people, and that population of people was a student body that made purchasing decisions on a regular. We created this event called Get REC. It was called Get REC because it was held at the Rec Center and basically allowed every business in the town to come in and put up a booth that wanted to sell to college students.

They ended up paying us several thousand dollars to come in and do that. Figuring out a healthy way to monetize our assets and get additional funding for the university was awesome. A great first job, and then I moved to San Francisco. I was tech robust and eager to move West. My first job in San Francisco was at Gallup, the Gallup World Poll. The thing that I was so excited about with Gallup, I don’t know if you follow any of their research but they are an academic company. It’s stewards of research.

A big part of what Gallup does is sell both employee engagement research and customer engagement research. I fell in love with the company for many reasons. One of the big things that they talk about with their leadership development is that the employees join companies and leave managers. It was this big, huge part of the thing we were consulting around. It was where I grew fond of leadership, education and development, the process of being a student, and becoming a great leader. I got some deep education on how to be a good boss. This was before I became a boss. I then was eager to go into tech, so I joined LinkedIn.

At Gallup, you were leading what BizDev or was its sales?

It was biz, and I was a seller. Our motto was fewer larger relationships. At the time, McKesson was one of my biggest customers. I’m spending a lot of time with them on leadership development and employee engagement. Incredible experience in consulting because you get to go wide. Not necessarily deep. Lots of exposure to different business processes across tons of different business types and unique companies. It was an incredible experience there over years. Living in San Francisco and not in tech, which felt like a misnomer, so I decided to move to LinkedIn. I started with LinkedIn right before we went public, and then I left LinkedIn, and we were owned by Microsoft.

A lot of things happened over that six-year window. My role inside LinkedIn changed almost every year. I led pretty much every customer segment, so from our smallest customer all the way up to our largest key accounts and in a couple of different lines of business. Both our talent solutions business and the sales navigator product when we launched that product, which is now over a billion in revenue.

It was incredible to be able to build something from the ground up based on an amazing asset, which is the LinkedIn network. I learned a million things from LinkedIn but one of the things that fueled the next phase of my career was selling into sales leadership, which is what a selling sales navigator did. As go-to-market professionals, there’s something meta about selling to sales leaders. I wouldn’t trade it for the world.

As go-to-market professionals, there's something sort of meta about selling to sales leaders. Click To Tweet

I get to talk to my peers all the time. It’s probably how you feel getting to talk to other experts. I learned from my customers regularly, which is incredible. I fell in love with sales leadership. Not just being a sales leader but working with sales leaders at LinkedIn. As I mentioned, I led all different customer types and in a couple of different lines of business. I felt like I had deep exposure to lots of different parts of go-to-market orgs.

The other thing I will say about LinkedIn, outside of it being a phenomenal company, is that it demonstrated to me how it should be done, how a business should be run, how to take care of your people, how to build a sustainable business, how to build a moat around your product and how to inspire a huge audience of a global talent pool. Best in class across many vectors that matter when building a sustainable business, so forever grateful for my time at LinkedIn.

I took all those learnings, decided to gamble a little bit of in the startup world, and went to WeWork, where we could spend the entire episode on that. Maybe we should grab a beer to do that. It was quite the run. I spent a few years at WeWork leading up to our at Ben failed IPO attempt and just wild run. I was running our mid-market business across the US and hired over 70 people.

My last job was to eliminate them all. It was a wild experience but if LinkedIn taught me how to lead in peacetime, WeWork taught me how to lead in more time and a major benefit to both. I learned a lot and worked with some incredible people at WeWork. I was there in the Adam Neumann era but I would say one of the things that I learned the most about WeWork was how to pressure test growth and ask yourself the question if something could be done faster, bigger or at a lower expense.

B2B 32 | Sales Forecasting
Sales Forecasting: Learn how to pressure test growth. Always ask yourself whether or not something can be done faster or bigger. If you can accomplish a task in six weeks, challenge yourself to do it in two days.


Challenging the status quo of, “If we can do that in six weeks, what would it take to do in two days?” It’s asking the question of pushing the boundaries of what you think is possible. Whenever I got a question from WeWork that was like, “I need you to do X, Y, and Z.” I always thought it was insane. Most of the time, we delivered.

There was something to that, which is that if you can apply enough pressure and enough resourcing, what you are able to accomplish is pretty incredible. I learned a lot there too. The next up on the rung for me was that I was eager to get back into the software. I was eager to get back into the ecosystem. I mentioned selling into sales leadership and so moved to Clari. Clari was, at the time, mostly an enterprise product. They were overhauling forecasting. It was their bread and butter.

Over the last few years, it has been incredible to be a part of a team that I deeply admire and respect. Our leadership team is phenomenal, led by Kevin Knieriem and Andy Byrne, which is so strong. Working in a space that has blown up when you think about revenue and sales tech is exploded, which is awesome to be a part of for lots of reasons.

First and foremost, as a seller, our function is last to evolve. Almost every other function had innovated and supplied its employee base with new technology to become more efficient and smarter in their work, except for sellers. We are finally getting our moment. Our moment is here, and we’ve invested, and you are seeing a huge amount of not just venture capital but excitement from investors.

A seller's first and foremost function is to last and evolve. Click To Tweet

Analysts are all over the space. It’s blowing up. If you look at sales tech similarly to the way that you looked at MarTech of the 2000s, it is hopefully going to follow a similar thread, which is lots of investment, tons of companies, and ultimately consolidation. It will be interesting to follow the space over the next ten years or so to see what happens.

Clair has expanded from being a forecasting platform that could help people overhaul a process to going into tons of different workflows. How do a company and a go-to-market org run their ultimate revenue process? How do you inform a rep to a manager one-on-one? How do you inspect opportunities? How do you spot risk? How do you ensure that your pipeline has enough coverage? Ultimately, how does a CRO define to the board and the leadership team if they are going to meet, miss or beat their number? It’s a very exciting time for us to be a part of.

Two things stood out for me. One thing you talk about is being meta, going back to LinkedIn, and selling to sellers. It reminds me of my time at SugarCRM, where we are selling to sellers and marketers. We need to be great at doing marketing and selling. That was a big eye-opening experience for me. You are preaching but are you doing the right things where you can lead by example?

I always say to my sales team, “We are demonstrating a sales process to the sensei, to the people.” Their inspection of our sales process, you can imagine, is going to be diligent. The way we show up in these moments is so critical. I would say that one of the things that are so incredible for me as a sales leader is the number of outreaches that I get from a head of sales or CRO complementing my sales team and asking if they can hire them. It is the best compliment because I know they are a tough critic.

There’s something that I want to pick your brains about clearly, you are an expert. You have been in sales, from a sales rep to leading a sales team, to now you are technically a business leader representing sales at the board level. How did you master or how are you continuing to master forecasting and prediction? That’s the biggest skill to learn.

From my personal experience, I have been at startups and worked with sales leaders. More recently, when talking about forecasting and missing the forecasting, here is a big miss where we forecasted $800,000 in a quarter, and eventually, sales closed at $30,000. I don’t want to go in there but clearly forecasting and being able to hit the number is a huge skill. What advice would you give to our readers on that?

It’s massive, especially as you move into sales leadership. As a sales rep, you are generally responsible for calling a number but very few orgs hold a rep accountable for their accuracy around that number. Part of that is because they don’t have a lot of diversification. If they miss one deal, it could throw their number off by several hundred percent, and that’s tough. Not a lot of accountability at the rep level. A little bit more so once you move into frontline leadership.

Naturally, when you get into executive leadership and sales leadership at the highest levels, the forecast is the thing that you are expected to get right. It’s table stakes to be effective in the role. If you don’t have a good methodology for how you get there and you have to put a good process in place, you are screwed. When you go into a board meeting, you are going to get eaten alive, and you need to be able to defend your call.

All that to say that there’s so much that is unpredictable in our environment that there’s no amount of machine learning, AI or fancy software that’s going to call COVID or the current downturn. Even the rise of PLG businesses is much harder to forecast in that environment because you are responding to market factors that you may or may not be able to predict. Velocity is all over the place. To get to the root of your question, there’s a handful of things that are core to getting this right. I’m going to walk through some very specific examples here, so forgive the granularity.

That will be the most useful for our readers, for sure.

One of the first things that you have to get right to get a good and predictable forecast process is sales stages and forecast categories. The terminology that you use inside of your sales org to call the way a deal is represented is critical to getting the overall process right. What that means is that you need defined stage criteria. This is what must be present inside of your deal for this to be considered a stage 2 or 3 deal however you have laid out your stages. Most companies have 4 or 5.

B2B 32 | Sales Forecasting
Sales Forecasting: The terminology you use inside of sales org to call how a deal is represented is critical to getting the overall process right. You need defined stage criteria inside your deals.


Within those stages, from qualifying to pricing and negotiations, however, that is enabled for you that it is crystal clear to a rep and impossible to argue when something has moved into or out of a stage. For example, in my world, we might say, “To move to stage three, we have to have been named vendor of choice.” This means we have to have gotten from the customer, the prospect, an indication that we are the partner that they want to partner with.

We might still need to get through security. We might still have an outstanding MSA but they have said, “We would like to move forward with Clari,” and now we know we have to move towards our paper process in getting a deal done but we have been named vendor of choice. That is a requirement to move into stage three. The requirements associated with stages and forecast categories are critical, and ensure that you’ve defined them. All of your leaders are managing to it is so important.

Now when you look across every single deal, you know that you are looking at the same set of requirements. You don’t have one deal that’s being represented differently than another deal with a different set of requirements. It’s foundational to getting a forecasting process in place. Second, there is no silver bullet inside the forecast. Therefore, you need to have a set of data that you can triangulate against.

For me, what that is, first, I have a rep roll-up. The rep roll-up is inclusive of all of the outstanding inventory. A lot of companies will do a bottoms-up view, which is deal by deal. They will say, “This deal is either in or out, or this deal has X amount of probability.” You have this bottoms-up view to informing one point of your triangulation process.

The next is you have a manager override or a manager commit. You have your leaders pressure test the rep-level forecast to see where they would agree or disagree based on how they might be called a deal. For me, the third layer is using AI. Specifically, inside a Clari, there’s a module called Pulse. Pulse is looking at historical data, and it’s making a prediction on how that quarter or a next quarter might shake out, looking at conversion rates and the amount of pipeline that we have to see how we might land. That means every single time I’m calling a number, every week, I’m triangulating between what the actual inventory says at the rep level, how my leadership team thinks we are going to shake out and what the machine says. Between those three, I’m landing somewhere in the range.

The first point you made is supercritical, which is my takeaway from that is defining very clear entry and exit criteria for each stage, where there’s no argument. There’s no ambiguity. Seller A can argue, “This is how I see it,” versus seller B will see it completely differently.

It’s black and white.

You use Clari, obviously in-house, and shout out to Clari. For those of you who are reading, if you are curious, check out Clari. Going back, if you have to go back in time and pick either a GTM success or a failure story, can you share one from your most recent time? That will be a great eye-opener for us.

I’ve got lots of both. Do you want me to share one of each?

Yes, absolutely.

There’s obviously recency bias here but I will share a failure. I will use one at Clari, which is we initially set up our go-to-market org to be geo-specific. We were going to have these little hubs. The hubs would be like if you owned Minneapolis, you were the CEO of Minneapolis Clari. Your job was to map out all the businesses that resided in Minneapolis, to get in with the Chamber of Commerce, to set up local events, and to create a community across companies that might sit in Minneapolis. You owned that geo. That’s how we structured it. This is pre-COVID.

You moved to a world where geo is almost completely irrelevant. I remember the moment when I knew this was a failure. I had an incredible rep who I very well love and still with us, who sold our first logo in Toronto. He said, “I planted a flag in Toronto, and it happened to be a relatively small deal.” You love getting a deal. A deal is a deal. I will never not celebrate a win but the win was that we landed in Toronto.

I was like, “This is one of our best reps. He is trying to crack into getting a small deal in Toronto. Why do I care if we are in Toronto? Do you know what I care about? Revenue. Why do I have him focused on these geos when there’s much bigger fruit if I were to distribute, let’s say, the market of New York?” We made this decision to move from a geo-based model to an account-based model a few years ago and never look back.

It was such a better distribution of our opportunity. Also, it allows us to hire pretty much anywhere and so we can get better talent without needing to focus on the geo. That was one, and I learned that way. A success, I will say, is that we were a pretty enterprise-focused company when I started. Most of our customers were enterprise customers.

There was a lot of trepidation to go down-market. People were fearful of the impact on ASPs. People were fearful of not having the support resources to support the velocity business. It took a lot for us to go down-market. One of the things that we did was pilot it with a handful of apps and gave them our smallest potential customers to see what they could do. This small team, we call it emerging. They exploded. It was all the fish that were jumping into our boat.

We decided to take that as a signal and say, “If these are a bunch of leads that are coming our way, what if we put capacity against it?” It did something with it instead of letting them come to us. It started with a small team and let them run wild for a quarter before we knew that this was a no-brainer place to invest based on the interest that we got and the success of that team. My regret there is that we should have done it sooner.

One question for each of the scenarios there. For the failure scenario, you mentioned you moved from geo to account level. I’m going to take a hypothetical example over here. Let’s say it’s Home Depot. That’s the account you are trying to break into. Were you assigning a rep to break into, let’s say, Home Depot in Michigan State versus Home Depot at any location? Is that the shift they are talking about?

We organize the account by HQ location. If Home Depot were headquartered in Minneapolis, then it would be owned by the Minneapolis rep but wherever the HQ location is would dictate ownership.

I had a question regarding your success scenario, which as you can clearly relate to this moving upmarket. Our down-market is super hard for any organization. What is the thought process for you and the leadership team at Clari on how you define the success criteria? Was it verticalized or how did you think about framing the team? Can you share some more insights about that?

It is a tough and big strategic decision. We operated more as an enterprise-grade company. We had enterprise customers. Most of our market position was geared toward the enterprise. That start there, which is how do you tailor your messaging and your market position to be attractive to different segment? Something we had to face in something we still deal with a little bit is you will see the SMB customer ask us, “Are we big enough for Clari or is it too soon for us to find value and benefit out of Clari?” If they are a former user, they never ask that question because they know what the value is to them.

For the general population, that’s where you need to start. Reeducate the new population of people that you are going after and why you are right for them. That was the one. One of the big changes that we went through as well is that naturally, at the market, you see enormous complexity. Both in the buying persona and the number of people involved in a purchasing decision and also for us technically. You are integrating with data.

B2B 32 | Sales Forecasting
Sales Forecasting: As you go upmarket, you’ll have more diversified personas buying from you. Be sure to reeducate the people you’re going after so that they know you’re the right one for them.


The way that data is structured can be very complex. Nuance for that unique customer. How do we simplify our process so that we could move through complexity at a different speed when we go down-market? We had this internal hashtag that we talked about. There’s a guy in my team named Adam Wainwright, who I will credit with this.

He labeled it supersonic. Supersonic was the charter for that team, which is, how can they move through a process quickly? If somebody said, “The average sales cycle time was 45 days, how could we get it to 30?” Everything we did was through the lens of supersonic. Taking what was a cumbersome process upmarket for a complex cycle and trying to figure out how we remove friction to get to a supersonic process.

I got some more follow-up questions for you on that. When someone goes to your website, you get the messaging, everything directed at the person who relates to like an enterprise customer, the ICP, versus when you are looking to go midmarket or down-market in your scenario. There’s the messaging, pricing, also other different aspects which we won’t get into. I’m sure you will share. Again, how did you think about that or how did you attract the initial set of your target midmarket customers?

Specifically, do you mean in the messaging that would be attractive to that?

It might be outbound because, obviously, you won’t be driving a lot of inbound or maybe you already have those in your pipeline, in your list somewhere, and then you segment that as the potential midmarket. What strategy did you use for those?

Firstly, we had to make a decision on what we would use to define segmentation. What was the best marker to signal that this type of company was indeed different from this other type of company? We ended up using just employee count. There’s a good debate on whether or not we should use sales employee count. The reason why we didn’t use sales employee count is that it’s harder to get that information and also different by industry.

Employee count is generally representative of the size of a go-to-market org that would be attractive to Clari. That was the first thing we aligned on. Not revenue, and that was by design. Employee size is the place that we started, and then we drew a line in the sand for us around a thousand employees. The other exercise you had to go through was, where does a cycle become differentiated? What is the line in the sand that says, “When you are below a thousand, you operate like this. When you are above a thousand, you operate like this?”

Those two things require a different sales motion, a different set of resources, a different market message, and a different price. Therefore, we are going to treat them differently. That is an intellectual exercise that should be run with product marketing. Hopefully, you have an ops function that can help support the data around that suggests, “You should stand up a motion that looks fundamentally different for this customer than that customer.”

After we went through the academic exercise to come up with an answer, then you go to trial and see if that’s, in fact, right. I will say that as our product and our go-to-market org have evolved, we have made some type of change to our segments most years. We collapse and expand. As we add more skews to the product, the way that we think about supporting them is different.

I will give one other example, which is in the presales side of the business. When we sell to a prospect, we segment by employee size, as I referenced. As soon as we sell that and it passes to the customer side of the house, and it’s going to be run by an account management team. They segment by revenue. Not by the revenue of the company but by the size of the deal that we did with that prospect. For them, the way that it makes sense to organize is how big of a deal it needs to be serviced and, ultimately, ensure that we can make that customer successful in a different way for different needs to segment.

Especially for customer success, it’s more of an expansion opportunity. Clearly, that makes sense. That is super helpful. Did you allocate six months or a year for this “experiment”?

We had prepared for six months and ended up making a decision after three. The reason why we decided after three is because it was so obvious that it was successful. We had done twenty new logos or something in a month. It was clear to us that applying resourcing there made sense. The other thing is that you get feedback anecdotally from your prospect base.

The number of customers that we had spoken to that appreciated got onboard with our supersonic approach and appreciated that they could move fast but it didn’t feel like a clunky, stodgy enterprise process. The feedback I got from many CROs in that space was aligned with the process we had put in place. It was very clear that we were going to make the investment. If you know that you are going to make the investment, why not move fast?

Let’s switch gears. We are coming to the final segment over here. What are 1 or 2 or 3 things within the go-to-market arena that you are curious about? What’s causing you to go deeper into research and shift your thinking from a go-to-market perspective?

There’s a ton. In no particular order, I will say the things that have been top of mind to me here. One is around intent. There are so many amazing new signals that we can incorporate into our sales process to try to find intent which means that we are going to use so much better at attaching the right accounts to the right resources. If we know the accounts that are warm and we put them with our bestsellers, we should be able to do all kinds of things. Not least of which is increase our revenue.

Lots of exciting companies. We happen to partner with 6sense. They are phenomenal on this front. Lots of intent resourcing here that changes the game for us. That’s number one. The other is around business models. The other thing you are seeing a lot more of is consumption use cases and usage-based models, and PLG motions. There are all these new ways outside your standard license-based model to structure the way you capture revenue from a customer. That’s super interesting to me. We will only see more advancements in the way that pricing in packaging is structured, especially in software. Those are two that are hot for me now.

There are so many ways outside of standard license-based models to structure the way you capture revenue from customers. Click To Tweet

The first one is intent, clearly. There’s a lot of talk in the industry about how you define intent. It has always been there in good market teams. You need to identify the intent signals but there has been no clear black-and-white way to identify them within the sales stack and marketing stack. That has been the biggest gap. Of late, I’m seeing more companies like 6sense.

There are others as well who are helping. They are also adjacent solutions that can say, “Plug this. Stick stack into your solution, and you can see the intent signals.” That’s from a tech perspective. I would like to get your thoughts on within the go-to-market team. How will you define whether this is a high-intent versus a low-intent account?

We use the signal that we are getting from 6sense primarily for us. We also use some G2 data, so we layer those on. The other thing for us is diversifying the leads. Not all leads are created equal. How do you ensure that you’ve got the right lead scoring so that it gets the right urgency that’s required? Naturally, a demo request or referral for us is high intent. We want to ensure that the speed to lead is short and that we can get connected to the buyer as soon as possible.

For us, that meant we instituted. I will give you an example. A product called Caddy. We are new to using it. It is the ability to book. If you book a request for a demo on Clari’s website, you would be directly connected to the AE that owns the account instead of bifurcating and moving away, going through all the other channels like being to an SDR or someone to do a qualification step. If it’s a named account, we already know that that’s somebody that’s already qualified by default, and we want to ensure that there’s as little drop-off as possible. That’s some of the mechanics that you have to optimize in the go-to-market.

One other topic, I have been coming across this topic also, and I speak to other go-to-market leaders. There has been a constant debate as to who owns the SDR team. Is it sales or marketing? What is your thought process around that?

I’ve seen it in both different departments. It obviously works in both places. At Clari, Kyle Coleman owns our SDR org. He is like LinkedIn famous.

He’s an SDR champ. I see him on LinkedIn. He is a true champ.

Deep expertise in the function, and so we are lucky to have him for lots of different reasons but that’s one of them. For me, he’s probably one of my biggest partners. There’s nobody I spend as much time with as Kyle in orchestrating a sales motion for us. Where it lives is much less important than the alignment between the two orgs.

B2B 32 | Sales Forecasting
Sales Forecasting: Where the SDR teams lives are much less important than the alignment between sales and marketing.


Even if it lived in sales, naturally, so much of the lead flow you would hope your SDRs are responding to is generated by marketing. If it lives in marketing, it must be responsible and accountable to sales. This is why there’s no obvious answer to this. Either way, there are tradeoffs. It’s not a perfect answer, no matter what. The alignment between the 2 orgs and, arguably, the 2 leaders is the most important thing.

Moving to the last couple of questions here, who would you credit if you were to go back in time? Who have been your code mentors and sponsors? Who have been the role models that helped you get to this point in your career?

I’m so lucky because I have many. You said 2 or 3. I will start maybe in logical order. The first time I ever went on a sales call like as an adult with a full-time job and going out to see a customer. I was with a guy named Aaron Nadolza. He and I both worked together at Gallup. We were going to our first big sales meeting.

It was his meeting, and I was just shadowing. He took me under his wing and taught me how to sell. Everything from how to set up a good meeting, how to follow up on the meeting, and the real basics of customer engagement. That’s like the least exciting thing he’s taught me over the years. I have now worked with him at three different companies. I followed him on LinkedIn. When I went to WeWork, I brought him over to be my boss.

I’ve worked with him for many years. I’ve learned a million things from him. The big thing outside of sponsorship, as you mentioned, is that he certainly sponsored me but he just deeply invested in me to teach me everything he knew. I was afforded his life experiences. I didn’t have to go through them myself, which was so incredible. Aaron has made a massive impact on my life.

When I went to LinkedIn, I worked for a leader that didn’t just change my professional trajectory but changed me as a human. His name is Peter Kim. Pete was the best boss that I have ever had. I remember specifically a one-on-one we had where I was asking him for some career advice. He basically said like, “Holly, I am yours. Use me however you want to use me but I believe in you. I’m here to develop you.”

What changed in the course of our interaction was that I did start to use him. A mistake that people make is that most people want to invest in high-potential talent. Where there’s often a mismatch is that the talent also has to go and engage and make good use of their resource. I took Pete up on his offer. I used him for everything, and honestly, I still do. We got to a place where he could give me advice about my whole life, everything from how to structure my mortgage to which job to consider or not.

Ultimately, it’s still your decision. It’s still your life but to have people that care deeply about you and therefore are interested in you making the right decision is so important. The last one is my current boss, Kevin Knieriem. He’s the CEO at Clari. He has invested in me in lots of different ways. One of which is to empower me to make my own decisions, build out an org, and be able to stand up for something that I knew was right.

I feel so empowered in my role now. Having limitless belief changes the way you operate. When you know that the person above you is in your corner and rooting for you in every way changes the way that you show up at work every day. Back to the comment, I made earlier about Gallup and that people join companies and lead managers.

For all the leaders reading, it’s a deep responsibility that we have as people leaders at any level. Whether you are leading leaders, managers or reps, someone’s happiness depends on the way that you approach them. You, as their boss, get to empower them. You get to ensure that they are going to have a good day or a bad day. That’s something that we shouldn’t take lightly. I have been lucky.

As a leader, someone's happiness depends on how you approach them. You have to empower your people and ensure they will always have a good day. Click To Tweet

That’s a great piece of advice there. For all readers, it doesn’t matter if you are a people leader or someone who’s reporting to a boss. You will have both up and down for most of you there. Hopefully, someone will take this as an inspiration to sponsor and grow someone’s career and vice versa. Ask and take, go full advantage of your manager because they sincerely care for your growth. That’s the message. Last question here, Holly, which is, if you were to turn back the clock and go back to your day one within the go-to-market career journey of yours, an amazing career journey for sure. What advice would you give your younger self?

One of the biggest things I have learned, which is so critical, is that much of the career decisions that we make can be convoluted when you start to add in title and comp and roll scope. You can get attracted to those things but one of the things that probably has the biggest impact on your return is the quality of the company. You are picking the right horse to bet on.

If you pick to be the assistant at the right company versus the CRO at the crappy company that goes nowhere, the fact that you have a big title, a big comp or whatever but the company doesn’t succeed. It ruins the whole game. Picking the right horse is 90% of the battle. If you take what is perceived to be a lateral move or even a step back in title and comp is so insignificant in the grand scheme of life and a long career. It’s so much more important to pick the right company and invest in the right company that you believe in over the long haul. It’s a big learning for me.

I have nothing to add to that. That’s a great piece of advice, for sure. Thank you so much, Holly. It has been wonderful speaking with you. Thank you for sharing all the wisdom and insights. Good luck to you, your sales team, and the folks at Clari.

Thank you so much. I appreciate you having me on the show. It’s great to spend some time together.


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B2B 31 | New Market

B2B 31 | New Market


Go-to-marketing strategies can differ based on location. If you’re starting a business overseas, you have to look out for certain things if you want the best brand-customer relationship. With Alariss, that won’t be an issue anymore. They help international founders launch their brands in the US. They help build their team, raise revenue, and lead with their product. Join Vijay Damojipurapu as he talks to the CEO and founder of Alariss, Joyce Zhang Gray. Learn why it’s so difficult to enter a new market. Discover how building relationships and partnerships are key to go-to-marketing. Find out some attributes you want in your go-to-market team. Start launching your business with Alariss today!

Listen to the podcast here


Launching Your Go-To-Market Business In A New Market With Joyce Zhang Gray From Alariss

I’m super excited to have a fellow San Francisco Bay area member on the show with me, Joyce Zhang Gray, who is the Founder of Alariss Global. She is with me. She has obliged to be part of this show. I got introduced to Joyce by one of my earlier show guests. I looked up Joyce’s profile, and it stood out. It’s a unique profile. Talk about Ivy League. She has checked the mark for the Ivy League background and Harvard undergrad and Stanford MBA. After that, she’s got a very varied offbeat track, but it all laid the right stepping stones to what she’s doing now. With that, let me welcome you formally, Joyce. I’m super excited to speak with you.

Thank you so much, Vijay. Thank you for the kind introduction and for inviting me to your show.

It’s my pleasure. We should talk about this at some point in time in our show. You’re a former employee at Y Combinator. You’re the first business person at Human Interest. I know someone at Human Interest. It’s a great company. They allow what they’re doing in the mission. You did that. After that, you took on roles outside of the US, which is in Asia, and tried to build the go-to-market functions. You also played the role of a UN ambassador. Did I get that right?

The timeline and the titles might be a little bit off. I worked for the World Bank. I also worked for the Federal Reserve, which is the central bank of the US. That was earlier in my career. During that time, I was overseas. I worked in Africa, Latin America, and Asia on behalf of American tech companies launching in Asia. At Human Interest, I was the first employee, not just the first business employee. I started talking to them in the midst of Y Combinator. I joined right after they finished YC, and we could be off to the races. I’ve experienced the depth and breadth of big companies, small companies, government agencies, and the US, as well as many other countries. I’m delighted to share some perspectives on this show.

This is all in a very short time span as well. This is super impressive and inspiring.

Thank you. I don’t know if it’s that short. I’m not as young as I used to be, but I appreciate the compliment.

I’ll start off formally here. I always start this with this question with all my guests. How do you define go-to-market?

I define go-to-market as the core function of a revenue-generating business. It is how you get to and appeal to and deliver value in many ways to your customers. Go-to-market will oftentimes be sales and marketing. Sometimes it’s customer success as well because it also involves upselling. Much of the revenue generated by many companies, especially B2B companies, is through expansion revenue, not through new revenue generations. Go-to-market covers all these functional areas and more.

B2B 31 | New Market
New Market: Go-to-market is the core function of a revenue-generating business. It is how you deliver value to your customers in many ways.


I completely agree with you. I would also expand and add products. This is something that I see a lot of functional leaders at small companies or even startups and large companies. They miss the holistic piece, especially in a technology company, a product-based critical role in go-to-market. The big trend that’s going on in the industry nowadays is the whole product-led growth. If you talk about go-to-market and lead product, that’s a big wide. I completely agree. That’s something I’ve seen play out, which is strong and impressive go-to-market leaders cross-functionally across these functions. It’s marketing, sales, revenue, customer success, and so on.

Having a great product that customers want to use, delights them, and want to share is what one assumes. In many companies or tech companies, you can divide it into two categories. It’s either the people building or the people selling. They’re selling what someone else is built, and the builders will continue to build and iterate based on what can be sold. It’s correct. I would also say even with product-led growth, it would be a misconception that the products can sell itself.

I know a lot of amazing tech founders who assume, “If I build it, they will come.” People need to learn about the product somehow. That’s where I focused on the other functional areas when I described go-to-market because I was assuming that there would be a preexisting product that’s very strong as a baseline for what’s needed to go-to-market.

With that, you mentioned the words sales and selling. Tell and share with our readers the story of what you do now and what led you to start at Alariss Global.

I’m the CEO and Founder of Alariss Global. As a CEO and Founder, you’re the company’s first line of defense for sales and the last line of defense for sales. Most tech founders go into selling or building, but for the person on the business side, especially the CEO, some of the major responsibilities I have and that other CEOs usually have would be customer acquisition/go-to-market. This can include managing marketing, sales, and account management.

As a CEO, you're the first line of defense for sales and the last line of defense for sales. Click To Tweet

The other piece is internal recruiting. That’s incredibly important, building your team, which is also another form of sales. Selling people on your vision and a career with you is highly important. Finally, it’s fundraising, which is another form of getting capital into the company so you can continue to grow. Those are some of the major responsibilities. There are other things, business operations, finance, and everything else that go into the CEO’s role, but those are the ones that are most relevant for this conversation.

You also asked why I started Alariss Global. I started Alariss Global from a place of real need. I, myself, was launching companies in other markets, going overseas, and realizing how inefficient it was and how I was not most equipped to be able to launch as effectively as I wanted to. When you’re in a new market, you have to learn and get up to speed quickly. You might also be operating in a market where you don’t speak the language. You don’t understand the culture. You don’t have connections locally. It’s a long and very manual process of building your brand and credibility, building your networks, figuring out how to partner with the right lawyers, accountants, and recruiters, and finally, building your team. After you build your team, you can start generating revenue and attracting your customers.

B2B 31 | New Market
New Market: When you’re in a new market, you have to learn and get up to speed quickly. You might speak the language, understand the culture, or have any connections. So building your brand is going to be a long process.


I thought that a lot of this could be a leapfrog, especially with modern technology. Why have an ex-pat go into a market they don’t understand and spend a lot of time and money effectively when you could immediately spin up a local GTM team, a Go-To-Market team that is highly specialized, highly professional, and knows exactly what they’re doing, and they can start generating revenue for you from day one? That was a lot of the impetus behind Alariss Global. I wish Alariss existed for me when I was doing this. Because it didn’t exist, I thought I would build the solution for everyone else.

That’s a story of all the successful startups where the founders experienced paying themselves. They did some quick early market research and found that, “There are no viable solutions, so why don’t I solve this problem?” Can you expand on that? I also want to emphasize that because one of the core audiences for this show is the founders and aspiring founders. What led you to that decision point where you felt that this was a pain point and a large business problem with a huge turn and opportunity?

It was clear to me that it was a large pain point that I wasn’t the only one who faced when I had friends who reached out to me. The light bulb moment for me was when I had consistent outreaches from many different types of people and friends who are founders across India, China, and other markets who would ask me for connections or referrals in the US because I was perhaps one of the few or most trusted American friends that they had. I could empathize with and understand them because I had lived and worked with them before in those markets. It was a good reminder to me.

Sometimes as a founder, this is your own form of go-to-market. It’s your personal brand and network. Oftentimes, for founders, who’s going to trust a no-name company out of the blue? It’s usually going to be your friends, your family, and the immediate network that gives you that benefit of the doubt and knows you and your reputation so they can take a risk on you. Once you have those early believers, it does accelerate to something more.

That was when I first thought a hint that this was a large and very strong pain point that many people I knew faced. I did a bit more research as I was helping my friends and found other people who faced the same problem. I started to scale it and began Alariss more as a consultancy with always the belief that I would turn it into a tech company. As a consultancy, it gives you a few benefits as a founder. Some people call it bootstrapping, whatever you want to call it. It does give you revenue right away. When we talk about go-to-market, the single source of truth is following the money or where the money is.

In go-to-market, the single source of truth is to follow the money. Click To Tweet

People can tell you all sorts of things. They can tell you, “Your product is amazing, Vijay. This is so revolutionary. I love it.” They tell you all these nice things, but they’re not willing to pay you for your product. This is great. This feedback is very flattering, but it doesn’t pay the bills. It doesn’t lead to a viable company. You need more than just people who will tell you what you want to hear. You will need them to tell you what you need to hear. Sometimes what you need to hear could be things like, “I would buy it, but these are the other competitors that I’m looking at or other vendors that are offering something similar.” Maybe the price point isn’t quite there, and then you start to hone in on it.

When you start getting people paying you for that, that’s when you know you’ve hit upon the true hurdles that you need to gravitate towards. Even when building a startup, I started it as a consultancy because I wanted to see what is painful enough that people will part with their hard-earned money and give it to someone else to solve for them. Finally, within that realm of different things that people find painful enough that they’ll pay for it, what is something scalable and repeatable that I can productize? That’s how I came to build GTM teams.

It reminds me of the time when I started my consulting company, which is Stratyve. I was not thinking about starting or doing anything around consulting and offering GTM services. About a couple of years ago, someone reached out to me and called on LinkedIn, and it turns out that the founder had this company based in India. They were looking to do a go-to-market entry in North America. They needed help building what should be the go-to-market plan, the business case, the positioning, the messaging, the target users, and the use cases. That was inbound. I was thinking, “I don’t offer this for free. I have all these skillsets, but you need to pay for it.”

Going back to your question, people will seek advice, but are they willing to part their hard-earned money? In this case, he said yes, and that was a quick validation. I said, “It falls in line with what I’m known for and what I enjoy doing.” People are willing to part their hard-earned money. We’re completely on the same page. As part of market validation, are people willing to spend on your services or products? That’s fundamental, especially in the early days. That was a core piece and the driver. You got the business validation around incorporating and why you started Alariss Global. Let’s expand. Who are your customers? Who do you serve? What products or services should they be coming to you for?

Our customers are some of the most ambitious and globally-minded tech founders as well as executives based all over the world, outside the US predominantly, who want to go-to-market and expand their team into the US. We say we’re a global expansion company, but our main focus is US expansion. It could be a founder based in Bangalore, Tel Aviv, Beijing, Cape Town, or Sydney. We’ve worked with clients on every single continent.

We’re very lucky to have had that opportunity. The pain point we’re solving is they want to grow their revenue. They want to enter new markets because it’s about customer acquisition and growth. Sometimes, you’ve either saturated your local market quickly. Let’s say you’re a Singaporean or an Israeli company. The market is quite small in your domestic market, so you start thinking overseas fairly quickly.

You could be a company that’s based in a very large market. Let’s say you’re based in India, but perhaps you’re a B2B SaaS company. You know that the B2B SaaS market is a bit more limited in India than in the US. It could be that you are already a unicorn, and you have tapped into or exhausted almost all of the markets in your domestic market already. Onwards and upwards, you want to IPO. If you want to IPO and become listed on NASDAQ, then you probably do want to have some presence in the US. Those are usually the types of customers we’re serving, the pain points they’re feeling, and their ambitions and motivations for why they want to work with us.

What is Alariss Global’s go-to-market strategy or plans if you can share that? You need to spread awareness. You also need to talk about, show and display your credibility, expertise, and case studies. What is your go-to-market? What does that look like?

One thing I want to emphasize here is that our go-to-market has dramatically shifted and changed as we’ve learned things and become more aware of our own capabilities and limitations in these markets. We started off with a lot of experiments. That’s something I want to emphasize to every founder. You don’t know what you don’t know, and just because it worked for someone else doesn’t mean it will work for you. If anything, if it worked for someone else, it might mean that there are no more opportunities for others who are later joiners to copy what was done previously. That’s something I want to emphasize. It’s important to read all these growth handbooks. It’s important to listen to shows such as Vijay’s, but you have to figure out your own path in this journey.

B2B 31 | New Market
New Market: You don’t know what you don’t know. Just because something worked for someone else, doesn’t mean it will work for you. And if it worked for someone else, that might mean that there are no more opportunities there.


I looked at a lot of benchmarks, but the difficulty is we’re defining a new category. We’re not helping American companies launch overseas, which is what most of the benchmarks I saw did. We’re helping overseas companies or international companies launch in the US. Still, I tried a lot of the same tricks of the trade. I looked into SEO, Google ads, LinkedIn ads, used social media, some outsourced SDRs, and all the different tools and tricks. The vast majority did not work. Luckily, two things did start to work. One was referrals and word of mouth.

That, as I mentioned early on, is always valuable. I was lucky to have a deep network already in the tech sectors of a lot of major overseas tech hubs. Getting friends to share news about me and offering very big discounts to the first customers so they could test out our products, give us feedback, and work with us, started to work a little bit.

Another is we would ask for referrals from the customers we worked with to new customers. Finally, we started to hit upon looking through channel partnerships. Channel partnerships are very difficult. It’s now become one of our main growth channels, but at the beginning, it was difficult because selling to a channel partner is even harder than selling to a customer. You’re trying to convince someone to open up your Rolodex to me and put your reputation on the line so I can have a shot at your customers. That is a hard sell. You need to first build up credibility. It’s important to go first through some referrals. We found a bottoms-up approach worth quite well for us.

If we had portfolio companies from a particular venture capitalist that liked us, we would ask them to share and promote us to that VC. Later, the VC would come to us and say, “A couple of my portfolio companies mentioned that they liked working with you. Maybe we should have a partnership or a volume discount for my portfolio company.” The channel partnership then starts to make sense because you’re not just a no-name risk that they’re taking that could impair their credibility. You become an augmentation of their brand and their reputation.

If they already know that companies they’re affiliated with or working with like you and trust you, then it’s very easy for them to come in and partner with you, and even better if they can take credit for negotiating a discount. It’s a win-win on all sides. You get the deal flow and save costs on your GTM because referral revenue comes with a much lower cap than a lot of other revenue. They also win because it makes them look good, and this is something their partners, customers, and portfolio companies want anyway.

If I had to summarize your go-to-market, initial traction, an initial set of customers, and leads that came through your own network, how you got started is you tried SEO, outbound, and so on. You would build your traction through word of mouth, your own network, and then referrals. It’s the same playbook. It’s the same thing for the channel partners. I’m a big believer. All the prominent startup advisors say the same thing. If you’re a startup, do not lean on channel partners as your primary go-to market. That should not be the first source.

You validate that thought process once again. For all the founder readers over there, this is the real mantra. Don’t lean on and pitch to your investors that you’re leaning on a channel partner as one of your good market strategies, not initially, at least. In your case, it came through reference. It came inbound. In this case, it was a VC who invested in one of the portfolio companies. That was your customer.

Another thing I would point out here is that it is very challenging. I know how it feels like a chicken and egg problem. If you are trying to build a relationship or a partnership from scratch, but you don’t have those, how do you build it? If you can’t build it because you don’t have preexisting relationships, it feels like an impossible task. Things do evolve. You work with a combination of the tools you have at your disposal and what works.

I know other people who have amazing networks, but their network is irrelevant because they’re building a B2C product. B2C is all about customer acquisition and user acquisition at a massive scale. Just because you know a couple of friends from business school doesn’t mean you’ll suddenly get a million followers on your new social media app. It does depend, and that’s also why I mentioned a lot of go-to-market is highly personalized and individualized.

A lot of go-to-market is highly personalized and highly individualized. Click To Tweet

What I’m sensing, and for all the readers out there, is that this is not your traditional product or service. It’s almost like you are building a platform play here. It’s a two-sided platform. The one set is your customers. The other set is all the salespeople across the different calibers and roles. Share your story about how you’re thinking about this two-sided marketplace. Going back to your chicken and egg analogy, it’s the same thing. How are you managing and maintaining that two-sided marketplace growth?

This is where it’s interesting because a lot of marketplaces have elements of both B2B and B2C. For a B2B marketplace, they still usually make money from the 2B part, but it is still important to have the 2C part. Many people liken this to building two companies at once, which is why marketplaces are incredibly difficult to build, but they are very difficult to unseat once you’ve built it. It’s a hard business model, but once you’ve cracked the code, it is something that is incredibly valuable and hard to copy. For the chicken and egg, I think about who is paying for this.

It goes back to what I said earlier, follow the money and the source of truth. I analyze the market. The job seekers could potentially pay, but most of the time, they won’t. Very good candidates don’t need to pay to get a job. If you ask someone to pay, you might not be getting the best candidates. Secondly, if someone doesn’t have a job and is looking for a job, they inherently have a limited ability to pay. By charging one side of the market, you are limiting and restricting your pool of supply, and you are getting worse supply. It was clear that that wasn’t going to be the angle we would tackle. We then looked at the 2B part, which we always suspected was going to be the better side to charge. The 2B side has high amounts of skepticism.

It’s this concept of how you get someone to part with their hard-earned money, especially if they’re founders and people who have to be frugal and scrappy. What value can you demonstrate to them? What can you show them as value? That is important to understand what value you bring to your customers. For them, the value was something that was difficult for them to get access to themselves. It was revenue generation quickly in a market that was highly important to them, with people that they otherwise didn’t have access to because it wasn’t within their network. We started by thinking about seeding this side of the marketplace as the most important. If you seed the 2B side of the marketplace, if you have great employers and jobs on your platform, the job seekers will come to you and be more likely to trust you. That’s what we did, and it started to play out.

You hit upon key points there, Joyce, especially in a two-sided marketplace. It’s about who will see the value and who will part with their hard-earned money. That’s where you go. That’s a B2B place or the play. The B2C is building your network of salespeople. Do you specialize in a specific industry? How do you build an asset, that sales talent pool?

That’s a great question. That’s more on the product side. To our earlier point, product-led growth or having the products involved in the GTM is highly important. Assessing the sales talent is part of the reason companies use us. Like I said, it’s core to the product that they believe this is a marketplace of competence and trust that we, with our experiences in the US and our networks, know how to both attract the right types of people and screen and filter out those who aren’t so great. We have a combination of online assessments as well as phone screens and interviews that we do.

We usually look for a couple of key things which are incredibly important when founders are looking at building out their go-to-market team. We look for intrinsic motivation and drive. Sometimes some people can call it hustle. Startups love that phrase, so I’ll call it hustle. For a startup, why I say intrinsic motivation drive is because it can’t be as simple as your boss telling you what to do and looking over your shoulder, or you get paid a lot of money, and therefore you are doing it. It has to be something more because sometimes startups don’t have a lot of money, and founders don’t have a lot of time. Management can sometimes fly out the window, and people need to be self-motivated.

B2B 31 | New Market
New Market: If you’re going to build your go-to-market team, you’ll want people who have intrinsic motivation and drive, the ability to communicate well, and empathy.


The second thing we also often look for is the ability to communicate well. I know it sounds so simple, but for someone in a go-to-market function, it’s critical. It can be verbal communication or written communication. Also, it has to be effective asynchronously because the founders we’re working with are usually based overseas. There are many time zones that separate them from their American GTM team. Even in the US, if you live in Hawaii, New York, or Colorado, those are all different time zones. Even for our team, we’re distributed across multiple time zones because most of our team is either on the East Coast or the West Coast of the US. There’s a three-hour time difference.

You want to be respectful of the time. For example, it’s 2:00 PM in San Francisco on a Friday. I know I’m going to stop messaging my US team on the East Coast once I’m done with this show because it’s going to invade their family time and their weekend time. I don’t want to do that. Communication is important. The last piece I said, which also ties into communication, is empathy. Empathy is so incredibly important. Like the example I gave, I don’t want to impose on people on their personal time and family time if I can help it. I’m empathizing with them because I want to know how I would feel in a situation. I also want to know how I want to treat others.

It’s so important for GTM talent to have strong empathy. Also, it goes beyond just working with clients and customers and getting their trust, but also working with diverse and global teams. It is important to be empathetic and patient because there are times zone and cultural differences. Sometimes you have certain situations that pop up that are less than ideal, but you need to empathize. If you always put that thought at the forefront of your mind of, “Everyone’s working hard. Everyone’s trying their best,” then even small things or mistakes can seem very immaterial.

Those are all great points. The more I listen to your story and approach, I’m being reminded of these unicorn companies like HackerRank and HackerEarth, similar to what they’re doing for developers and helping these employers find great developers. You’re doing a similar playbook for sales.

We are, in some ways, like the inverse of a lot of these developer companies.

Let’s switch gears a bit over here. Can you share a success or a failure story? It’s up to you what you want to share. I don’t expect you to share anything confidential and private, but if you can share a go-to-market success, not for Alariss Global, but for one of your customers, like what the situation was. Have you helped them in their go-to-market in a new market?

I’ll do that. I’ll share success. Those are always more fun. I’ll keep names and privacy intact. I’ll make it a bit more anonymous. We have worked with quite a number of different companies all around the world. In one company we work with that’s in the industrial automation and AI space, the team had tried for many months to hire someone in the US but was unable to. They were starting to fall behind because it was a venture-backed company. They were at the seed stage. The problem is the longer you delay being able to deploy that capital, and nowadays, when founders raise money, 90% of it goes towards the headcount. Very little has to go towards other things like where you pay a little bit of your cloud subscription fees to Heroku, your CRM, and G Suite or whatever. You buy everyone laptops.

Beyond that, especially with distributed teams, what else are you spending money on that is on compensation, bonuses, and benefits? They were having a hard time hiring someone, and it was frustrating them because they were starting to miss their revenue targets because it was taking so long to get someone in the market. The founders themselves were already fully at capacity. They couldn’t keep being the only salespeople because sales and go-to-market can accelerate. It can grow exponentially, but it is still going to be limited based on the number of go-to-market people you have on your team, especially for B2B of a certain ACV above $50,000 a year or so. A lot of decision-makers and a lot of your buyer persona expects to be able to talk to someone and have their questions answered.

It was starting to be frustrating. The hero in the story here was that they found Alariss through a referral. They started working with us, and we were able to get them the right person and get that person onboarded within a month’s time. To some companies, it might seem crazy like, “I took six months, and it only took a month.” Keep in mind that the American labor market is incredibly dynamic, and salespeople are good at selling themselves. If they can’t even sell themselves, how can you have confidence they can sell your product? A good salesperson, if they’re on the job market and are actively starting to interview, can get competing offers and other offers within two weeks. It’s important to remember this is dynamic. It moves quickly.

It takes a month from start to finish, starting with sourcing, screening, and attracting the salespeople and all the interviews they have to go through back to back with the different founders to finally offer letter negotiation and then onboarding. That is a lot of work to pack into one month, but it can be done, and it should be done because the longer it drags out, that means perhaps the company wasn’t moving quickly enough and wasn’t making decisions fast enough. They were losing a lot of candidates in their pipeline.

Perhaps they were working with the wrong sourcing partner or strategy for finding candidates. Whatever it is, it could be tough. After the person started working for the company, and it was a great mutual fit, the person had the exact engineering but also sales background that the company needed, and the company offered this person great growth and trajectory for advancement that the person couldn’t otherwise get from staying as a mid-level or mid-market AE or senior AE at a much larger company.

Becoming the head of North America right away for this company was exciting. A few months in that this person was hitting, achieving, and exceeding revenue targets, the company wanted to hire more people, and then they were able to use this momentum, and the revenue that was being generated to close a very sizable series A with an American investor, even though this company was headquartered in another market and the founders because of travel restrictions were unable to come to the US at the time.

That’s a great win-win story there. It’s a win for Alariss, but clearly a win for the salesperson who got hired. He or she’s on a different growth trajectory, and for the founders as well, because that whole approach of working and partnering with Alariss led to them raising series A in the US market from a US investor.

Let’s switch gears again to a different topic. You have a wide network from your undergrad and grad schools, and you work with different organizations and communities. If you were to share some of the best practices and what resources you lean on, be it podcasts, books, communities, or mentors, what resources do you lean on for your personal and professional growth, especially given how stressful, but at the same time, fun the founder journey is?

The founder journey is stressful. You’re right in that. I’m lucky my husband has been such a bedrock of support for me from the beginning. He was my boyfriend at the time when I started Alariss. I quit my job and started Alariss. It was all these highs and lows. It was a bit of a strain on our relationship at first. We had been dating for a little bit, but it was probably a side of me he hadn’t yet seen how high the highs can get and how low the lows can get. I’m so lucky that I have his support. That means the world to me, and it means a lot.

With other people for inspiration, I have a couple of other friends who are founders that I will text or call up. Everyone’s busy, but people make time for each other. I’ve been so touched and floored by how generous people are with their time, even though it’s limited. I remember, in particular, some of my female CEO friends are ones that I found I resonated with even more or others who are minorities and are founders in the US because there is a special shared experience. There are certain elements that are unique. For example, I had my first child while I was running Alariss and while I was fundraising.

That is a different perspective when you ask a friend who’s been through pregnancy, hormones, pitching, and fundraising than if you were to ask a founder friend who had never been pregnant before or was a male and had gone through pregnancy vicariously perhaps through his partner, but hadn’t experienced it himself. It’s incredible to find a community and find either comfort, solace, or advice. Finally, my team has been great. I am so appreciative of how hard they work and how much they care. It makes me want to be a better leader. It makes me want to run a better company because they believe in me.

The founder's journey is a difficult one. Find a community where you can get comfort, solace, and advice. Click To Tweet

I’m so happy and grateful to you and the people supporting you. This is fundamental where you have “the right set of support system.” Things are unique when it comes to women founders and women leaders. They have their own unique set of challenges. As a man, I can “relate” to it, but it’s not the same thing. My wife and I have these conversations as well. She keeps sharing these experiences that she’s seeing at her workplace, and it’s different.

I completely respect that. Kudos to you and all the support systems that you have in place. We’re wrapping up. Coming to the final question here, if you were to go back in time and to the day one of your go-to-market journeys, possibly, maybe it’s that first day at Human Interest if I have to recall your career path and journey, what advice would you give to your younger self?

The beginning of my go-to-market journey was when I was living in China, working for an American tech company. This is right after I graduated from Harvard with degrees in Economics and International Relations. I worked at the Federal Reserve, which is a perfect fit for my degrees because it combines economics and international relations because I was working on a lot of policies that pertain to our international stakeholders and partner central banks around the world. I go from this very ivory tower, high-level policy, intellectual stuff. Most of what I did was memo writing and research, both in school and at work. I show up in China, and I have this glossy notion of what my job would be.

It’s going to be like I’m a diplomat in some ways. I’m coming as an American to China to build offices in China. I had never worked in business before, so I had this conception that it was almost like being a diplomat. You go, spread around the country, meet people, and shake hands. It’s great. I showed up, and they said, “Your title is sales director.” I said, “What?” I had thought at the time, as perhaps a lot of people who go to these types of universities do, I thought sales was a dirty word.

It’s that guy who keeps trying to push the used car sales or random people following you on the streets, trying to hand you flyers, trying to push things on you that you don’t want. That was what I thought sales was. I started off being a little bit apprehensive, and I didn’t even want to say or admit that I was doing sales, but that’s what it was. When you’re growing a business overseas, that is exactly what you’re trying to do. You’re trying to sell the company and the product in a new market.

Later on, over time, I embraced it. Now I have tremendous respect for it. I use the word sales all the time. I own it. The core piece of my responsibility is to sell the company, the vision, and our product. At the time when I was first beginning, I had too many apprehensions. That’s something I would want to share with founders and especially those who find themselves in a GTM role. The only reason people look down on sales is because a lot of people give it a bad name, but like anything in the world, that’s meaningful if you work hard at it and are good at it. This is a crucial function. It’s a crucial skillset to have.

That’s a great piece of advice. For me, I was having the same notion, plus I was also having a fear of selling. I started my consulting company Stratyve, reached out, and spoke to a different set of people because I needed to wear multiple hats as a consultancy service delivery person, but at the same time, marketing and even different functions within sales. You got the outbound, the BDR piece, and then you have the account executive piece who is negotiating and closing. I was also studying top-tier salespeople, and a common theme that surfaces, and I’m sure you would agree with this, is that great salespeople are great listeners. It’s completely contrary to the popular notion that’s being floated out in society, which is salespeople talk and talk. On the contrary, great salespeople listen more than they talk.

I agree. You’re a very good salesperson, Vijay. You’ve been a great listener. Thank you to everyone on this show.

Thank you for your time. I wish you and your team the very best. Thank you so much, Joyce.

Thank you. You too. Take care.


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End-users are the best source of feedback on a product you are launching. Giving value to the voice of the customer can help you realize opportunities and provide the best solution. In this episode, Shruti Kapoor, the GM and Founder of Wingman, talks about how validation and differentiation play into making your solution stand out and ensure that your platform doesn’t only analyze data but ultimately affects change or improvement in an organization. Get tips on how you can build a level of trust and leverage your customers’ feedback in getting your business to scale. Also, get insights on when and how to connect to Y Combinator and set yourself up for success. 

Sales in the times of an economic downturn.

Listen to the podcast here


Voice Of The Customer For Your Startup Success With Shruti Kapoor

It’s been a good several months since the last episode was released, but my commitment from now on is to be consistent. That’s my promise to my readers. It’s not just you but for my selfish reasons, I look forward to and enjoy speaking with the go-to-market leaders. In this episode, I have the pleasure of speaking with Shruti Kapoor, who is the Founder and CEO of Wingman. It’s Wingman by Clari because of the acquisition. We’ll go into a lot of other details, but I’m super excited to be speaking with you, Shruti. Welcome to the show.

Thanks, Vijay. Let’s get this season started with a bang. It sounds like this is the first one of the season.

I’m curious. What led you to go and live or work in Dubai? I believe you grew up in India. Is that right?

That is true. Yes and no. I did spend the majority of my life in India, but I spent a decade in Singapore somewhere in between. I moved to Dubai in 2022. In many ways, I’m enjoying the change. Being in a new place makes you relook at everything with a new lens. The business reason for this was as part of the acquisition, I wanted to be in some sense closer to the broader action. Given the constraints with visas, there are not as many countries as Indians that you can quickly relocate to. This seemed like a good fit from a time zone perspective, access to Europe and generally, very well connected. Here I am.

Especially the time zone and the access. You talked about the visa situations and all that. I’m glad that you relocated. You look to be that person who always looks for change and to be out of your comfort zone. You mentioned growing up in Singapore and India and relocating to Dubai. I’m super excited about that. With that, I want to transition a bit over here and then go into more of the first question, what I typically ask of my guests, which is how do you define the go-to-market?

There are two things that a company needs to do, build something and then make sure somebody is using it. The t-shirt I’m wearing says, “Make something people want.” This is the Y Combinator motto. I think of go-to-market as anything that helps you get your product into the hands of users.

I would love to get into the story of the whole Y Combinator. I was looking at your About. It was nice and creative as to how you came about and told your story of how you found that pain point and your cofounders, and what made you get into Y Combinator and so on. Let’s get into that. That’s a good transition. It looks like you were leading the go-to-market and sales team. You ran into this problem with your product. Even marketing folks ask you, “Can you get customer feedback?” That was the genesis of this. Tell me more about the story. What did you and the team do to go down this path?

Before I started Wingman, I was working at a company called Payoneer, which by no means can be called a startup. They did an IPO in 2021 or so back. At the time when I was working with them, I was the third employee in India. They were trying to enter this new market. My role was to help them figure out their go-to market. The way the team was structured was there was a central team, which was doing marketing and product. They would have regional teams that were doing more customer-facing roles, partnerships, customer success, sales and a variety of other things that show up.

There's a lot of value in having the voice of the customer for teams outside of sales. Click To Tweet

What that did was it made the distance that exists between customer-facing teams, marketing and product teams much more stock than it is in usual organizations. That gap always exists but in this case, it made it much more stock. We were launching this product into the new market for the first time. There was a lot of stuff that we needed to learn from what the customers were telling us and take back to the rest of the organization.

It wasn’t always easy. I’m sure all of us have had that experience where we tell the product team, “The customer said that,” but it goes in one ear and comes out the other. If they happen to be on a call with the customer, it has a very different impact. They’re suddenly like, “That’s why the customer wants it this way. Let’s see if we can prioritize this on the roadmap.” In that process, what we realized was there’s a lot of value in having that voice of the customer for teams outside of sales as well.

As a person who was on the sales side, everybody faces so you have folks in your team who are doing well and folks who are not doing well. Sometimes everybody seems to be putting in a lot of effort but getting very different results. You’re wondering what you can do to help them. That was my other challenge. Those two things came together. We were like, “Both of these problems can be solved if we could go back and analyze every call that happened between the customer and the salesperson. We could also get broader insights from it because nobody has the time to listen to every call recording.” That was how this started.

When you were doing this, you found that problem. You must have done some market research. Were there alternative solutions back then?

There were a couple of solutions that had started. In our space, two competitors have grown well, Chorus and Gong, which both also started at the time when we were doing our initial research. Maybe they had a year of a head start at that point. We saw that almost as validation. When we look at problems and you don’t find anybody else trying to solve them, it’s almost a question mark. “Is there something that I’m thinking is wrong?”

In this case, the feedback that we got very consistently early on was, “I’m not sure if my sales reps would be okay to record their calls. Forget about it. Even if my sales reps were okay, I’m not sure if my customers would be okay to record those calls.” Honestly, if you were in that ideation phase and five people told you that, you would be like, “That makes sense. That’s why nobody else is doing this.” Some competition is good.

You bring up a very good point, especially for startups. You’re paying with so much risk and many variables. You want that market to be validated. There’s a lot of talk about category creation and all of that but you don’t take that approach with the startup on day one versus the category creation coming later on. A good lesson insight for founders, current CEOs and aspiring founders is to make sure that there is some market validation. I have seen where people go down a path and burn their money, time, motivation, energy and the people in 1 to 2 years but nothing happens. Kudos to you and your team of cofounders to take that as a validation and a hypothesis that’s already been tested out. You don’t need to do that.

The other thing that I learned through that process of early market research was when you have a solution for any problem that you have, there is a way that somebody’s already trying to solve that problem. It doesn’t matter whether there’s a direct competitor or not. There is always competition of some sort. It’s important to find whatever that closest thing is. Go and figure out that even with that closest thing, what are the challenges that people still have?

B2B 30 | Voice Of The Customer
Voice Of The Customer: If you are looking for that co-founder, your best bet is to make sure that you spend time and effort in finding that person who’s complimentary to your skillset because that can make a big difference in how much you can accelerate and how lean you can stay.


Early on when you’re trying to make that initial product and do that minimum viable product, you say, “I have to do all of these things, which are going to give me parity with the existing solution. I have to build all these other things that are going to give me differentiation.” If you go and speak to users who are solving that problem with whatever is the closest competitor to your solution, you should go and spend time with those users. Not with the context of, “Will you switch to my solution?” It’s with the context of, “What can I build that will add value to this person without me having to build everything else that exists?” It’s a very easy pitfall that people make. You can easily delude yourself into building products for two years and not having a single dust to it.

It goes back to the whole Steve Blank and others who have promoted this, which is a lean startup philosophy that has done that from the early days, which is good. How did you go about finding the customers of Chorus and Gong and other alternatives?

It’s a little bit of serendipity and the fact that Silicon Valley is a bit of an eco-chamber. If there is a SaaS company and it’s based in the Valley, there’s a pretty good chance that their first hundred customers are also based in the Valley. If you speak to enough Valley companies, you’ll find somebody who’s heard of that company or using that company. That was broadly how it happened.

Switching gears here. With the problem, you found that there is market validation and a need based on this. The next step was you met with your cofounders, who are the CPO and the CTO. There is that problem-finding phase, market validation phase and, “How do you find my cofounders?” That’s key. Tell us and share your experience with the readers as to how you made that happen.

The order was a little bit different. I met my cofounders before we necessarily zeroed in on this idea. The way I met Murali, who’s the CPO, was through a common friend whom he went to college with in engineering and went to college with me in my MBA school. At that point, Murali was moving back to India. He was very clear that he wanted a startup. He had previously worked in a very early-stage startup that had gotten acquired by Google. He had seen that startup life and Google life. He knew where he wanted to spend his time. He moved back to India with the intention of starting up. That’s when we met.

At that point, I still have a full-time job. We started discussing and ideating. We went through multiple ideas before freezing on this one. Srikar and Murali have known each other for a long time, since their first jobs in 2005 in EntreLogy. Broadly speaking, every company probably has different founder-team stories. If somebody’s looking for that cofounder, unless you already have somebody who’s complimentary to your skills, spend time and effort in finding that person who is complementary to your skillset.

That can make a huge difference in how much you can accelerate and how lean you can stay. We were a founding team of three people. We had different specializations in some sense. We could afford to keep a relatively small team. There was so much tech and product work between Murali and Srikar that could cover. It helps to make sure that you stick to what you need to complement yourself and find that person.

Know your strengths, which is self-awareness and know your gaps as well. The key is to find that person who not only will cover your gaps but also from a chemistry and validation point of view, you all click. That’s key. Before we dive or go further into Wingman, your target audience and whom you serve, here’s one final question on the early days of your startup journey. How do you prep for the Y Combinator pitch? What advice would you give to people who are looking to apply for Y Combinator and other incubators?

When we look at problems and we don't find anybody else trying to solve them, it's a question of whether there is something wrong or what we’re thinking is completely wrong. Click To Tweet

You should think about whether or not it’s going to help you, depending on where you are in your stage of the journey. At least with Y Combinator, our experience was that if you were at the point where you were either building that product, doing user research and figuring out what was your value proposition, it was a great, time and phase to be in Y Combinator. There is enough and more advice on what Y Combinator evaluates and how to go through that interview process.

I don’t think there is a real secret sauce. It’s just a lot of clarity in terms of saying, “This is the problem that the startup solves. Why has nobody else tried to solve it before? What does the competition look like? Why do we think we are going to succeed?” As we went through the process of preparing for the Y Combinator interview and the application process, we spend a lot of time answering these questions as three founders sitting in a room and going through them.

A lot of these things became clearer to us to the extent that I was like, “At this point, it doesn’t matter whether or not we get into Y Combinator.” The interview preparation process has helped us so much in thinking clearer and crystal. Some of these external things work as forcing functions. It’s important to make sure that you know the other questions that you need to answer first. It’s easy sometimes to go in the flow of the building, working and hustling, whereas you might not have figured out some of the basics.

I like the fact in how you phrased it, which is irrespective of the outcome of the result when you go through the whole Y Combinator application process. The very fact that the questions are the problem statements that the Y Combinator application is putting forward will force you as a team to realize where you are in the journey, whether this is the right thing and whether you are going in the right direction or not. Switching gears, let’s talk about Wingman. You serve the salespeople but with sales, you got different titles and roles. Whom do you serve? Why did they love Wingman?

One of our early insights as we were doing our market research was when I’m building a product for recording and analyzing sales calls, I can serve anybody. I could be serving product teams and helping them get user insights, for example. What we realized was that the first thing is the team that you choose to serve, your stakeholders, are the people who at least have the ability to influence the adoption of your platform. The natural thing for us was you can’t get this adopted unless the sales leader decides to get this adopted. Therefore, you better make sure that the sales leader is an important stakeholder in your product.

The second thing was we noticed that a lot of times people were looking at this and this happens with a lot of sales tools. It’s a legacy because of the way salesforce operates. No sales rep ever believes that salesforce helps them. They all believe that it helps their manager. They’re only spending time in salesforce because their manager needs them to. What was important to us was to say, “This should be a platform that doesn’t just serve the manager but the sales reps as well.”

Ultimately, it doesn’t matter how much insight the manager has like, “This is what happens in the calls at Wingman. These are the things that my reps are doing wrong.” At the end of the day, the reps have to be the people who are taking the action to correct those things. Unless they are the ones directly involved, you are creating additional loops. If those loops don’t close, then no action happens. For us, that was a very early insight so we were like, “We have to build a platform that directly helps the sales reps and ideally, helps the sales managers by making sure that the sales reps can help themselves.”

Going back more into the tactical and doubling down on this thing, how many user research calls you were doing a day or a week during this whole process?

B2B 30 | Voice Of The Customer
Voice Of The Customer: As a founder, you must be the face your customers see. You have to be the person they trust.


We did it in maybe 2 or 3 batches. Before we started, we spoke to around 20 to 30 sales leaders who were more directly from our network to validate the problem and understand like, “What would you do? How would you use it?” This was before we wrote a single line of code. Once we started building the product, our priority was to make sure that we could have people who could use it and then give us feedback. That was the tinkering part. At that point, we did a bunch of interviews and maybe that was around 30 or so as well.

The third phase was that once we had figured out the product and we knew that we wanted to do real-time insights and this is what the meat of the product needs to look like, we then went and did two months. This coincided with our time at Y Combinator where we said we will go and speak to hot companies. Specifically, in our ICP, we’ll be very strict about whom we qualify. Three phases happened for us.

My peers in other startups and I struggle with this. We know the concepts of ICP. Defining the ICP, trying to reach out, doing the research and then getting feedback is a challenge. As an example, I can come up with an ICP of, “It has to be a company that has at least 5 employees or 1 location.” That’s a broad profile with multiple markets, industries and use cases. How did you narrow it down? You have a very limited amount of time. You’ve lined up all those people from a validation point of view but how did you lock that ICP?

It’s easy to get greedy and there is always that temptation. You’re trying to tell a bigger story to the market, the investors and everybody where you’re like, “This is a $20 billion market. Everybody in the world can use it.” It’s easy to go into that zone but very early on, make sure that you have something that is useful for somebody and you’re not building for two years, which essentially means that you have to find a small segment. Later on, you can expand your product and segment.

For us, there were a few things. One was we realized, “Is this generally a well-accepted technology?” The answer is no. “Does it influence user behavior?” Call recording is somewhat difficult for people to accept the first time. That’s true. Essentially what that means is you need early adopters. People who are early adopters in our case are specifically other tech companies. That’s broadly true for a lot of people.

The next thing was, “Do I sell to anybody who is in the tech space? Could it be a service provider or a product company?” That was the other distinction. The third distinction was, “What is the size of that sales team?” I could sell to a single founder or a 1,000-person sales team. “Where do I want to play?” What we realized was early on, there’s a sweet spot. We don’t want to build a self-serve product on day one. We want to be able to build a product that delivers more value than just recording calls and transcribing them.

There’s going to be some effort for adoption. That led to us saying, “It has to be at least a 10-member sales team that’s going to get the most value out of this.” With the product maturity, the time and energy that you want to spend on creating something very customizable, the settings and all of that, maybe you don’t want to work with a 1,000-member sales team on day 1. We then narrowed it down further and said, “Maybe it’s 10 to 50-member sales teams that we want to work with.” That was our process.

Thank you for sharing that amount of details. Your user is the salesperson. Maybe it is the BDR or the AE. The buyer is necessarily not them. It’s going to be the sales manager to whom the BDR or AE reports so you need to get both on your side.

The team you choose to serve your stakeholders has to be people who can influence the adoption of your platform. Click To Tweet

From a sales process perspective, it’s a fairly top-down approach. We would engage with the head of sales or the sales manager. When it came to us selling our product, they would then do a top-down on telling their team to adopt it. The ICP has expanded and we work with larger companies. We have the ability to also segment out the complexity of the product and the features by saying, “I could have a very lightweight version for a single user team,” versus, “I can have fairly sophisticated features.” Early on, it’s important to keep that narrow.

You completed or covered the journey from founding to getting your initial set of customers, investing, fundraising and all of that. If we switch gears over here, you were at a point where you are making single-digit million dollar ARR when Clari acquired it but it’s still a big jump from your first 5, 10 and 15 customers to getting to that million ARR. What is your growth trajectory? How did you make those investments as a CEO, plus handling the whole go-to-market? What were you scaling? What are your growth channels? How did you go about doing that?

It was interesting because we were building a product for sales teams. I wanted to be as close to that sales process for as long as possible so that, 1) I was also the user of the product and, 2) I was getting a lot more direct feedback on how every customer or prospect was receiving the product. What that meant was that to a large extent, early on, I was the only salesperson, the only SDR. I was doing my outreaches, cold calls, demos and closing the deals.

We only hired a head of sales close to hitting the $1 million mark. What that allowed us to do was to learn very quickly and make sure that we were also users of the product or at least I was a close user of the product and the rest of the team was as well. How did we think about that investment? We made some mistakes along the way as everybody does. The first was we did try to, in some sense, outsource this early on. We worked with somebody who was going to be a fractional head of sales for us, even before we had the first salesperson. The idea was this person can go set up the playbook and the early meetings and then help us accelerate that process. As a founder, you have one million other things to also take care of.

Our biggest lesson there was that early on, the customers are not buying the product because they trust the brand. There isn’t a brand. The product is likely getting built after you’ve promised it to the customer so they also know that very likely there isn’t a product. The thing that they’re going to trust if they were to make a buying decision is you. Therefore as a founder, you have to be the face that they see. Once we learned that lesson, I then amped it up to say, “If I have to be the person that they trust, let me build my credibility around it.” I then invested a fair amount of time and energy in interacting with that ecosystem and getting to know other folks within sales.

We had zero networks to start with because I had never worked in the US. Ninety percent of our revenue comes from that market. It was essentially being very conscious about saying, “I am the face of the company. People need to be able to trust me. Part of building the brand for the company is also building the brand for me.” I was going through that process. That helped us because a large part of our revenue comes from inbound interest. The flywheel had to kickstart with us putting a lot of these things in place.

Can you double-click on that? You’re getting to the point where a bunch of questions were running in my head. Early days, it’s going to be outbound but at some point in time, that outbound cannot scale, especially with you doing the outbound for the most part. Somewhere along the line, you had to do content, G2, analyst sites and others. You need to broaden your brand presence and awareness. What were the investments you made in the different phrases? Paid would be one I would assume and then content but you need to drive traffic to the content both on paid and organic. What do the growth channel phases and investment look like for you back then?

Firstly, paid was not something we invested in or got a lot out of, at least for the first few years. I think of it as layers of cake. You have to think of it as what can help people build trust. You’re only building trust with me while I’m still trying to build the brand for the company. The second layer of it is once I have those first five customers, can I use them to help build trust with others? You’re not going to show up on the top of G2 when you have five customers but you can still get good testimonials from them and leverage them whether on your website, outreach messaging or working with them. Be very conscious about it to say, “I worked with you. If you like it, then can we use this for building trust?”

B2B 30 | Voice Of The Customer
Voice Of The Customer: When you get good testimonials from five customers, you can leverage those on your website or in your outreach messaging.


The third step was you multiply that. If you have 5 customers and hopefully, either through testimonials or references you’re able to get another 5 each, then that makes it 25. That’s a great number. You layer it to say, “Now that I have 25 customers, maybe it is the time to go and hit review sites and other channels.” It eventually also depends on the persona. Salespeople are much more likely to speak to other salespeople to get advice on, “How are you doing something?” A product or an engineering person is very likely to go and do their research on Google and use that to base decisions.

The peer recommendation factor within our industry is much higher. We knew that we had to invest much more in that. It wasn’t just review sites. We spend time and energy being part of communities and their forums, understanding what questions people ask and making sure that our customers could represent us on those forums and discussions. That was a big growth lever for us. All of this is free. It doesn’t cost you money to do this. It just requires you to be thoughtful.

Something interesting happened. One of my customers referred me to a podcast host and said, “I want you to speak to this person.” That triggered a whole set of positive activities of its own. I thought, “Maybe this is rather a good channel where I could get the voice of the brand heard by more people while still being scrappy and not spending a ton of money.” As it turned out with the pandemic hitting and everything, that first year I must have done some 30 podcast interviews with different hosts.

That was also a great time when people were figuring out what they could do in the remote world to stay connected. There was a lot of activity and we were lucky to be in the middle of it. You have to be very aware of where your user hang out so that you can go hang out with them and how you can amplify that trust factor.

You were asking all your customers, “Where do you hang out?” Was it that simple?

To some extent, yes. When you’re building a sales tool, it’s interesting because you’re a user of that product and the people that you’re speaking with are also salespeople so they’re your peers. In a non-COVID world, they’re happy to go grab a beer with you and exchange secrets. It’s about being at the same events and then finding out, “How would you learn that? How did you go hire that person?”

I love the fact that you were not investing blindly in paid. It was all organic and more driven out of curiosity. That’s the sense I’m getting. Curiosity and the sense of intent as to, “Let me learn more about my persona and the people I’m serving. They’re using my product but what else can I be doing and how else can I make sure that while I’m serving them, my brand and my product is getting amplified?”

People often underestimate listening. I’m not just saying this in a sales conversation but even in the broader market conversation. One of the things that I recommend every salesperson to do when they join my team is, “Go find ten social media sales influencers and follow them.” It doesn’t matter whether or not you go on a sales call but you need to know how they think, what language they use, what is troubling them and what is aggravating them.

Build a product that delivers more value than just being able to record calls and transcribe. Click To Tweet

With social media, we have access to those things for free and unlimited. Sometimes, it’s too much. When people say, “How should I be using LinkedIn,” most advice is like, “Build your profile and brand. Post every day.” It’s much more important to post five thoughtful comments a day on other people’s posts than to post something of your own every day.

Coming back to staying curious and serving your person, which is a sales team and the sales managers, it looks like your team has come up with the economic downturn analysis. Do you want to share what that is? What drove you to that? How people can learn more about that?

This quest for me started at the time of COVID when the world seemed to be suddenly going toxic. One thing that I kept hearing from casual conversations that I was having with people on social media or online was, “We are not able to sell because everybody has frozen budgets.” I was like, “Does that hold true?” I got curious. I went and searched all of the call transcripts that we had or at Wingman to see how often is that coming up and whether that dramatically changed because of the pandemic.

What we realized was that it had changed but it hadn’t changed as dramatically. The biggest factor was getting deals to be lost. To our surprise, the biggest factor was timelines. What had happened was that suddenly everybody had this feeling of paralysis because they didn’t know what was going to come next. We’re in a shocking state. That was when we got curious about the data.

In 2022, we are going through a big tectonic shift in some sense. We decided to go back and look at the numbers in 2022’s context to see what happens if people are talking about the economic downturn and sales calls. What are some of the things that then impact win rates for deals? There are lots of interesting things there about what has changed about discussions on discounts, budgets, timelines and everything. One of the interesting things that we’ve learned is if people talk about ROI conversations, their win rates for deals increased by more than 30%. There are lots of nuggets like that. Maybe we should share it with the audience.

That’s key. When I work with my sales team over here in my current role, I’m seeing that they’re trying to find it difficult. The obvious question then comes, “What’s the ROI? Why should I buy or switch now versus not do anything?” Framing the conversation around the value but at the same time, showing clear ROI matters. This has been a great conversation, Shruti. Going more towards the closing stages, I got two questions for you. Who are maybe the top 1, 2 or 3 people that have influenced you and shaped you as a person and mentored you in your career growth and journey?

The biggest influencers as we grow up right early on are our parents. In my case, it’s my father’s fearlessness. He sent me to Singapore to study. I went there alone. In those days, it was probably a little bit more of a leap of faith because you couldn’t communicate as easily. There was no video calling. A call will cost you a bomb. That example showed me the value of being fearless and taking your chances. That’s made a huge difference.

Over the years, there have been many influences. One was a previous manager of mine. His name is Kiran. The one thing that he taught me was, “You don’t have to accept all corporate mumbo jumbo for what it is. You can always stop and question things.” That’s another important thing that we sometimes overlook. Overall, there are lots of books and media that I learned things from but the personal connection would be the main ones.

B2B 30 | Voice Of The Customer
Voice Of The Customer: It doesn’t matter whether or not you go on a sales call, but you need to know how your audience thinks, what language they use, and what is troubling or aggravating them.


Switching to the last question here, if you were to go back in time and go back to day one of your go-to-market journeys, what advice would you give to your younger self?

First is always asking the question, “How am I building trust with this person? What is my best lever to build trust?” The second is don’t take what people say at face value. Observe their behavior rather than their words. Not out of maligned intentions but people often behave very differently from what they say or think they do.

Thank you so much for your time, Shruti. It’s been a wonderful conversation. It was enlightening and insightful. I’m sure all our readers will benefit from this. Wishing you at Wingman the very best for the future.

Thanks so much, Vijay. I had fun.


Important Links


About Shruti Kapoor

B2B 30 | Voice Of The CustomerI have worked across lifesciences research, investment banking, technology investing, commercialization, product development, fin-tech and sales enablement using AI(current). I enjoy working in the interface between technology solutions and business needs and have worked in leadership and business development roles. I am also a trained Life Coach through Erickson Coaching and would love to have a conversation with you if you are feeling lost about your career or relationships or life in general. Also, interested in consulting for innovation and technology scouting & adoption.


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B2B 29 | Go To Market

B2B 29 | Go To Market


How can you focus on key aspects in your business for growth and organizational effectiveness? Listen to today’s episode as Jamie Cleghorn shares his experience in go-to-market. Raised by a data-driven marketer dad, he believes that marketing is in his DNA. He is part of Bain & Company which focuses on driving transformational change with clients, primarily in growth strategy, go-to-market effectiveness, and organizational alignment. He researched companies doing well, trying to isolate variables and discover the elements that drive above-market growth and share gain. This study found the pieces that he believes will define the future of the go-to-market.

Listen to the podcast here


Customer Engagement Success Through The Go-to-Market Strategy With Jamie Cleghorn

I am super excited to welcome Jamie Cleghorn. Thank you for being on the show.

I’m happy to be here. Thanks for having me.

With that, I always start with this question, which my audience love which is, how do you define go-to-market?

It’s everything that’s between a value proposition and a happy customer. The precondition for go-to-market is strategy. It’s having a clear sense of what are we building, who are we building it for and why would they give you perfectly good US currency in exchange for it? Once you have that, it immediately devolves into go-to-market like product management, marketing, sales, post-sales success and all of those things.

In some camps, it might be a bit controversial to put a product into the go-to-market. In my experience, when you don’t have a product in the go-to-market consideration set, in that value stream, it usually breaks down. Getting a product in there and building a straight line from that value prop to the customer is what you’re trying to do.

This is super crisp and helpful. I’m so glad that you highlighted the role of the product in the whole go-to-market sequence. When I speak with quite a few folks in the go-to-market world or even a couple of guests on the show, there are times where I need to remind them that it’s not just about marketing, sales or post-sales. Product plays a very important role, especially if your go-to-market is around product-led growth. You better have product front and center in those things.

We could all sit here and say that a good product manager is going to be customer-centric and they’re going to be needs-based. I cannot tell you the number of organizations we walk into where we say, “Show us the one piece of paper where you’ve written down crisply what the value proposition of this product is?” It’s not there in many cases. Sometimes they ran out of time. They were too busy getting the development sprint done or whatever it was.

Without that Dick Tracy decoder ring of why would a customer want this, marketing and sales mix it up. Customer success gets shipped to a new deal and the first question they say is, “What were you promised?” Pulling that thread back to square one around, “What is the promise we’re making here? What is the value we’re exchanging? What is it that we’re doing in a need-based way?” That is the bedrock and it’s hard to do well. It’s hard to raise a simple short letter.

It does remind me of a practice that is promoted or emphasized at Amazon. I’m sure it’s emphasized pretty much anywhere where go-to-market is a central focus area, which is when you’re embarking on a new initiative, a new product or a new product release, start with a press release as to why someone should care about it. Why there should be so much buzz and excitement in the market and then let’s work backwards.

B2B 29 | Go To Market
Go To Market: The strategy is the 1% and the go-to-market defined as product on down is the 99%.


We will do something similar, which is like, “I’m your first customer. Sell me your product.” Why should I care? The answer is usually in there. It’s not like they haven’t thought about it. They just haven’t translated it from feature to benefit or they haven’t put their selves in the shoes of a buyer or different members of the buying committee and thinking through the different pieces of it.

Switching gears a little bit over here, going big picture and on the personal side of things. You are a successful partner at Bain, a leading strategic consulting company. It’s a known global brand. Tell us about your journey. What led you to the path of management consulting and what do you do at Bain now?

I’m a born, raised and trained data-driven marketer. My dad was a data-driven marketer. I was aware of it from the youngest ages. In some ways, it’s in my DNA. His dad was an advertising and newspaper publisher. On the other side, I’ve got technologists and psychologists. This whole intersection of go-to-market using words to stimulate action and communicate has always been there. It’s always captivated me. I grew up wanting to do that and did that professionally until my late twenties and then I got bored with it. I no longer wanted to have the go-to-market seat at the table largely because I found it too constraint, honestly. It was too much on the order-taking end of things.

I went to Bain to be a strategist and to open the aperture, think bigger and do that work. It was great. I loved all of that. In fact, strategy, however, got boring again because you can only do so many market studies. You can only do so many plan briefs before it has to immediately devolve into the hard work of bringing it to market and building that innovation for real and all of those things. I ended up back in go-to-market land. It’s that Einstein quote of, “Success is 1% inspiration and 99% perspiration.” The strategy is 1% and the go-to-market defined as a product on down is 99%.

Most strategies aren’t bad. Most companies and executives won’t sit around and greenlight a bad strategy. They greenlight good strategies. It then dies a death of a thousand paper cuts on its way from product to marketing to sales and to success. I spend a lot of my time working with organizations to clear out the pipes between strategy and success, realigning, accelerating and redesigning go-to-markets. I lead that product and IP for Bain globally, which is a lot of fun. I work in lots of industries, primarily technology. You name it, I’ve probably worked on it. I bring a lot of the lens of why do people change.

Every consulting engagement ends with things people need to do differently. Whether or not they do them is the difference between a book report and a result in the business. That’s not very much fun to work on book reports. I spend a lot of time making sure that everything we do is dialed in to what’s going to work with our clients, what they’re excited about, what they believe in and harnessing the energy that’s existed inside their company to make the right next change and the next step on their journey as opposed to a corrective if you will.

I love the quote that you mentioned. To be honest, I can relate to a lot of the things and the conflicts that you lived through and have been through for several reasons. One is when I was doing my MBA at Cornell University. As you very well know, MBA grads are flooded with consulting job offers. Being me and being like many other people at Ivy League schools, I was contemplating whether I should pursue a consulting career.

A part of me went, “Consulting is nice. It looks cool and sexy but for me, what gets going and why I’m excited is more of being in the weeds, that execution piece, which you mentioned.” Fast-forward post my MBA days, I have been in the industry in an execution capacity. Over the last few years, I flipped where I started my own boutique go-to-market consulting company. I did that for a few years. Again, that bug bit me, which is, “Consulting is fine, but again, it’s all about execution.” Now, I’m back full-time at a Series B startup leading strategic growth function, which encompasses product-led growth and mid-market enterprise growth.

Go-to-market is everything that connects or has everything that's between a value proposition and a happy customer. Click To Tweet

Going back to what you mentioned and you can come up with all the research and the strategy, but the fun part is putting that into effect and seeing, as you mentioned, towards the end of your little story and journey is a lot of it has to do with change management. Change is hard and that’s where good, strong and a good amount of leaders come into play where they recognize that and they are empathetic. They are vulnerable and they come across like that. They coach the different functions and stakeholders in pursuing that change.

One of the most powerful tools in that is co-creation from square one. We can often tell if a consulting engagement is going to end in results are not measured by how engaged the team is on the client-side. If they want to be executives and get the book report every month and say, “Thank you,” that’s not a great sign. If they’ve got people at all levels of the organization and we’re doing workshops every other day, we are trying things on and we’re discarding them. We’re trying a new thing. I did one of those in 2021 and we ended up in November 2021. They rolled out a new price packaging architecture in December 2021 and January 2022 as a pilot. It drove immediate success. I was talking to the leader. Their win rates were accelerated and are higher.

Everything about it mixes up. It’s a great story and that was before the full rollout. That was a picture-perfect example of co-creation with a client. We’re bringing the best of our science, our tools, our experts, their domain expertise and their knowledge of how their company works. What organs are going to get rejected and which organs are going to get accepted and crafting something that’s slotted right in. The one trump card in all change management is success. If you can figure out how to show success early, you’ll get people to change their minds quickly.

This is something that I am focusing on and telling my team here in my new role is focused on the quick wins. Do little experimentations around customer acquisition, experimentations around onboarding, first user touchpoints and experiences and even pricing. Do those little experiences, get the data and then that data, yes, they might be “failures” but it’s more of a feedback loop. Once you see that early quick wins, that will give the juice, the boost and the morale to the team to change.

What I’d add to that is for any company, go-to-market is a system. It’s hundreds of people. It’s lots of different sales and marketing technology. It’s like a house with 100 additions. As the manager of that, and you’re like, “What should we add on next? What room should we renovate?” The art of being a good go-to-market leader is exactly what you said, which is I’m always running a bunch of experiments. When I see something that works, I go and remodel that kitchen or I remodel that bedroom or whatever it is. You never want to tear down the whole house or you won’t have anywhere to live. You got to make a quarter. If you’re always constantly optimizing continuous improvement, it’s a fun way to run a business.

I know you alluded to this a little bit. It looks like you and your team have been doing some research around how to improve the overall B2B sales and B2B go-to-market. Now is a good time for us to deep dive into that. Do you want to walk the readers and us to the research that you’ve been focusing on so far?

I would love to. It started with an insight that we had a number of years ago, which was that there’s this thing called a sales play that a lot of companies were running. Those work because what they did was they were the transversal. They broke down the functional silos and instead of saying, “Product throw it over the wall to marketing, marketing throw it over the wall to sales and sales throw it over the wall to success.” Sales plays the transversal that cuts across and is that direct line from the value props to the customer. We also had run into clients and companies that were running sales plays, but to no great effect. We had this thesis that the play was valuable, but it was really the system around it.

It’s somewhat similar to the work we had done with NPS. Bain created the NPS score in the ’90s. We said, “It’s not the score, it’s the system.” You can have the score. It’s like getting the credit score, “I have a score,” but like, “What are you going to do about it?” How are you going to build the feedback loops around that? The research we did was to look at companies that were doing it well, try to isolate those variables and say, “What are the elements that drive above-market growth and share gain?” We boiled it down to five things and that’s what the research said.

What we found empirically through our research is that the companies that did all five of these things were almost three times as likely to outgrow the market as the companies that didn’t. It was very intuitive to us in how we got there and it was great to see that the data bear it out. We think that these are the five things that are going to define the future of go-to-market, in part, because the companies that are winning and taking shares are the ones that are doing it. They’re the ones that are going to be left at the end.

B2B 29 | Go To Market
Go To Market: If you can figure out how to show success early, you’ll get people to change their minds pretty quickly.


It all starts with a very data-driven view of where the dollars are in the market space. Most companies can tell you, “We’ve got a 20% market share.” What they can’t tell you is, at client X or at prospect Y, what’s my share in this product category? When we build that for customers, it’s like turning on the lights in a dark room. You’re like, “Here’s where the money is in the market. I now have a map of where all the dollars are both in my retention, new logo accounts and my expansion accounts.”

Building that and building a robust view of that at a customer prospect and by-product level. We had a theory that you could build that process at scale and at speed. We’ve done that. We do that for clients now and we call it the money map. It’s a map of where all the money is in the market. Companies have different potential models, but having some data-driven view of that is critical because, without that, you’re only guessing.

I’m all for believing in the instincts of the front line, but their instincts on what the dollars are not always spot on. The second part is a factory that builds the play and the insight there is it’s cross-functional. Sometimes I call it the iron triangle of product sales and marketing. You need to get all three of those constituents together and if the three of them together architect to the play and say, “Here’s the messaging. Here’s the cadence of marketing actions. Here are the clothes,” and make that a group effort on building that as opposed to what we often see in companies of sales saying, “I haven’t gotten the marketing yet.” Marketing is saying, “I’m waiting for the product brief.” Putting them together, embracing that agile mentality and building that play in the factory brings it to the next level.

The next piece is an advanced command center that uses that data on customers and uses that library of sales plays and does the matching. You can call it the next best offer or it could be a place where you have a lot of opt-in. We’ve done this with a big technology company. They had a portfolio of sort 10 legacy products and 5 new strategic products. This is a way to say to the reps, “Pick three and pick two. You can sell three of the old thing and you can sell two of the new thing, but that becomes your account plan or those five plays you’re going to run there.”

That’s empowering for the reps and it’s a way to shift the mix in a very constructive way for the company faster than they would just by waiting for the salesforce to adapt to the new thing. That is that win room, which also then is your test and learning center. That’s where you talked about those experiments. It’s monitoring, tracking and it’s making micro-adjustments. At the frontline of the execution, because the plays are articulated, you’ve got marketing and sales working in tandem a lot better. The swing factor there and what we found is coaching. Two-thirds of reps wouldn’t pay $1 for an hour of their manager’s time but some reps would pay $500 for an hour over their manager’s time. That’s because their managers are giving them really good coaching and they’re helping them hit their number, exceed their quota and all of those things.

Really zeroing in on the coaching element there, for us, is the swing factor. The fifth is technology. It’s getting that RevOps Tech Stack engineered. We found that the winning companies that were three times more likely, they had eleven pieces of sales and marketing technology. They’ve architected a system, but the ones that were losing share and undergrowing the market, they had nine pieces. It wasn’t about buying the tech, it was about integrating the tech, marrying it to your business process and then getting it in the workflows. All those five things together, that’s what it takes to outgrow the market.

If I reflect on what I captured and this is where you can correct me if I got all the right elements. The first is all around data. Making sure that you’re capturing the right data and even looking at the existing data that you have around which of your products and customer segments are performing better and why. How much more room is there to grow within those customer segments or customers?

On a customer level but add a named customer or a named prospect level.

Life's too short to work on things where the intention isn't there. Click To Tweet

It’s to add an account level. The second is having that magic triangle is what I would call, which is the product, marketing and sales. If I can chime in, I would even add customer success if you are a B2B SaaS. It’s a triangle/rectangle, depending on whichever business model you have. I get the essence. It’s not operating in silos, as you said, but all of these functions working hand in hand. That’s critical.

The third is around looking at your entire product portfolio set, both the new offers that you have, the existing or the legacy. Whatever you have right now, you can package it well again. I’m going to give you an example. It’s not to promote Samsung, but this is the example that I came to where I was purchasing or pre-ordering the Samsung S22 Ultra phone.

The way Samsung packaged is, “Yes, we will give you a free upgrade on the memory, but at the same time, we are giving you $250 of instant credit in the Samsung store,” which means now I’m buying not just the S22 Ultra by also got the Samsung watch, which I was not planning to. It’s an existing product and a new product packaged together and sold. That’s an example right there.

The fourth one is around coaching. This is where a lot of go-to-market leaders have to invest in themselves, even if it means getting a coach for themselves. Because the way I look at it is, a role of a leader or a manager is to ensure that their team is successful. For that to happen, you need to coach. For you to coach, you need to know how to identify the growth areas and how to teach. Yes, you may be the expert in a specific subject matter, be it pricing, packaging, selling or qualification but if you can’t, you’re doing half the job and not the full thing.

Specifically, in sales, most sales managers were last year’s really good rep and this year’s mediocre sales manager. That’s a pretty high turnover industry. Teaching people constantly how to coach, particularly in sales, but also throughout the go-to-market value chain is so important.

The fifth one is having the systems and the right technology to tie all these pieces.

CRM, marketing automation, AI overlays, Cadence softwares and all the bells and whistles you see. All the things that all your readers get called on every day for a demo of this or a demo of that. There are 10,000 sales tech and MarTech companies out there. There’s no lack of things to buy there. There’s no integrated suite out there.

It takes a sophisticated RevOps or commercial ops person to say, “Here’s our value flow. Here’s our CRM. Here’s our marketing. Here’s where we’re going to tie it together. Here’s what we’re going to add in a Clari or Kong or Chorus or an Outreach.” It’s all the things like that. Getting that dialed in is tough. That’s why RevOps leaders are in such demand right now.

Tying back to what I’ve seen at the times when I was doing my own consulting plus what I’m doing in my current role is, there is a tendency where a lot of people buy technology because they have the budget and they need to spend or because their peers are doing that. They’re not flipping and asking the question, “What are the insights that I need? What are the gaps that I’m not aware of that I need to know of so that I can make the right decisions for the team, the executive leadership and for the business overall to serve the customers?” Ask those questions first and see if you have the right toolset, be it your MarTech, sales tech or whatever. Even your BI like a Tableau or something and then go for that tool.

B2B 29 | Go To Market
Go To Market: If you’re always constantly optimizing continuous improvement, it’s a fun way to run a business.


I love BI. BI is not intelligent. BI is visualization. You have to ask it intelligent questions and it can give you intelligent answers, but there’s no native intelligence in BI. Go-to-market used to be pretty simple. “Here’s your product catalog, your patch and your quota. Good luck.” What we’ve seen with COVID and everyone being at home, we’ve started this massive specialization of labor. You’ve got top of funnel demand gen, SDRs, BDRs, handoffs to the AEs and then expansion reps. We’ve microparsed it.

It’s like Adam Smith’s pin factory. Everyone’s down to their very technical thing, but if they’re not operating in a system, it’s like a random walk. What we believe is that the modern revenue leader needs to be a systems engineer or designer. It’s usually not about spending more money. You talk to a CEO and they’ll say, “I’m spending 10%, 20% of revenue on go-to-market. Isn’t that enough?” The answer is, yes. In fact, you probably already have all the technology you need, you probably have the right headcount. You might not have the right skill profile, but they’re not knit together in a way that they all work.

That’s what we need to get companies to do is to figure out how do you bring all those elements together and make them work in an orchestrated harmonized way. It is the system that we talk about, the five elements of the system. Those are the five elements to get to that orchestrated and harmonized high-performance machine.

I’m glad that your team did the research and reinforced the five key foundational elements. If you step out, a lot of these insights are common sense. Not to downplay the research or the clients out there, but somehow along the way, people lose sight of this. That’s why I’m glad that you did the research and you’re reinforcing this message of all these five pillars being in place.

It’s hard to see the forest when you’ve got to chop down trees every day. That’s one of the luxuries we have as consultants is we get to come in with fresh eyes and a good sense of what good looks like and say, “Here’s how you might want to lay it out.” That can be powerful for companies.

I’m super excited. Congratulations to you and your team, Jamie.

Thank you. It’s a fun piece of work and it’s fun to talk to clients about it.

Let’s switch gears. You’re at a very strong and good vantage point where you can step out and see all the different client scenarios and different industries where things are working or not working when it comes to go-to-market. From your broad breadth of experiences, it’ll be ideal if you can share two stories. One go-to-market success story and another go-to-market failure story because behind every success, there have been a ton of failure stories, which people don’t realize. If you can share a success story and then a failure story or vice versa. It’s up to you.

I’m going to have to change the names to protect the innocent here. We maintain our client confidentiality. The successes come in two flavors. One, I like to call them steroid shots. They are for businesses that are doing well and just need a little bit of an injection. Oftentimes, they’re a victim of their own growth. They’ve posted 30%, 40% year-over-year growth. They’ve added product complexity and segments. Complexity is multiplicative. It’s pretty easy. The product, sales and customer but as soon as you start to match, there are lots of failures to fall down.

Culture eats strategy. All of this will succeed if you can do it in a way that resonates with people. Click To Tweet

We do a lot of work around packaging and pricing, which almost gets back to market-led product strategy, coverage models, handoffs or capacity planning and all of those things. It’s building the next generation of the growth machine. Those are fun projects and those are with good companies with good products that just need a roadmap for the next leg of the growth. Those are great and fun to come back to a year later and find out that they were successful and how they did those.

The other flavor of success is these epic journeys. In my own personal business, we do a lot of work with private equity. Private equity has a saying, “No bad assets, just bad prices.” There are plenty of companies that have good bones in place but have lost their way in the market. Oftentimes, there’s a technology transition that happens. We worked with one that missed the pivot to the cloud.

They were public. They started shrinking. Their top-lines started going backwards, negative 5% year over year and their private equity bottomed. We worked with them and we got them back to growth, but it was a multi-year journey to retool that whole go-to-market. How do you call on cloud infrastructure providers and not enterprise data center providers? That was a big example, and that was product, sales motion, marketing, success and services. It’s everything around those.

Those are high risk, by the way. A lot of things need to go right over a long sustained period of time, but the particular one I’m thinking of right now is a very successful publicly traded company that’s posting sequential growth and is out there acquiring. We are using that business we worked on as the cornerstone of something that is working. I’ve alluded to failure early on. It’s when those conditions for change aren’t there. My least favorite consulting engagement was a few years ago. We went in and built a growth strategy.

We were going to do all these cool things and everyone was getting excited. We got done and they are like, “This is great.” We checked back and they’re like, “We haven’t made any progress.” We found out that they did that exact same project years prior with a different consulting company and they did that exact same project years prior to that with a different consulting company. We should not have taken the engagement and we didn’t know that. Had we known, we wouldn’t have.

Life’s too short to work on things where the intention isn’t there. Maybe that’s not a failure in a failure story for you. There are other failures where the mind’s willing and the body’s weak. The change is there, the change gets started and it stalls out. We’ve got a lot of tools to get ahead of that, but you can’t always do it. Sometimes the urgency of the quarter or the other thing or cost reductions or whatever it is means that you can’t see your way through to bright. Those are tough ones.

Thank you for sharing those stories. Going back to the failure story that you mentioned, it’s almost like you have the intent and in your case, a client had the intent to figure out and do research and understand what went wrong or what is going wrong and how to fix it, which is the first part. That’s where they engaged your team. There’s the bigger piece, which is, “Here are the set of recommendations. Do we have the appetite and hunger to execute?” That’s a big piece. It’s almost like they took the first step, but then they forgot to take the next five steps.

That’s why I like working in private equity because no is not an option. It doesn’t take too much for somebody to say, “This is risky. We might risk next quarter.” The reality is, if you don’t change, you’re on a slow slide to irrelevance. Tech companies, you’re either growing or dying and it takes courage. Courageous leadership is important here.

Let’s move on to another topic, but still, stay in the realm of 2022 and what you’re seeing across in the various industries and clients. It’s up to you how you want to frame it or share, Jamie. What is top of mind for you and your team for 2022 or what do you see as the top of mind for your set of clients and what are your recommendations when it comes to go-to-market?

B2B 29 | Go To Market
Go To Market: Teaching people constantly how to coach, particularly in sales, but also throughout the go-to-market value chain, is so important.


What’s top of mind for us is this research we did because we can get on point for what everyone needs. A couple of things are top of mind. One is this idea of technology. “We’ve invested in the technology. We bought all the toys. We bought all the things and it’s not working. We’re not getting the lift we want.” That resonates with everyone we talked to. Alignment resonates with everyone we talked to. Part of it is this work-from-home dynamic. We talked about handing it off from product to marketing to sales. That is not working anymore.

It’s not working when people aren’t in the same office and don’t go to meetings together and can’t get on the whiteboard and solve it or brute force their way through it. I was on with a COO yesterday of a big $20 billion technology company talking about marketing. The whole conversation was with marketing and sales alignment. Is the MQL dead? Sales would say, “I don’t care about MQLs. That’s marketing grading their own homework.”

SQLs are what I care about.

I think everyone’s tired. I think the world’s tired. With the Great Resignation, everyone’s short-staffed, working hard, dealing with personal sickness or extended family, which has been utterly tragic. Figuring out how to get up tomorrow and go to work, much less go to work and make it better and how to do it in a new environment.

This is where the coaching element comes into play, going back to your study and research.

Failing’s okay, but failing over and over for the same reason and not getting coached that’s a frustrating place to be. Those are the things that are top of mind. We all saw the world didn’t stop for COVID. There’s so much capital pouring in right now, whether it’s LBOs, growth equity or what have you. Sitting still, jogging and running are not an option. Everyone must be sprinting to keep up with the pace of change and expectations of the investment community. There’s still a lot. It’s a dynamic situation out there.

There are two points that come to my mind. The one I’ll share is almost like an approach or a solution or a mindset thing. It’s going back to your point of there’s a lot of capital that’s flowing in. This means the intent is there, but it’s almost like, “I’ve got all this money. Let’s put it to use,” versus what I emphasize in my team and broadly is, “Let’s operate with the mindset of we have a very limited budget. Let’s do the experiments.”

We’ll take two or three months to figure out what scales, which channel and what efficiency is being very diligent when it comes to the targeting, the messaging, the call to action or the offer. Focus on the basics. Once we have that, we can then pour money and scale that. It’s almost like a founder’s mindset. If you go back to the early days, the founder has this mindset. Unfortunately, when the founder has to hire and expand the team to tens, hundreds and thousands of people, that mindset is lost. It’s gone.

I was reading something. I can’t remember, but it was a founder or somebody who worked in startups and they said, “Doing go-to-market and a startup is drilling for oil. You’re going to drill a lot of dry holes and you’re going to try a lot of things that fail.” When you hit, put in a pump and pump, pump, pump. You can scale that thing up. It’s all about having a fast feedback loop, failing quickly, testing quickly, and iterating.

You don't win with good strategy. You win with a good enough strategy and great execution. Click To Tweet

It’s all about operating in two weeks sprint cycles, “For the next two weeks, let’s test the segment.” “For the next two weeks, let’s test this messaging.” It’s not that you need to go sequential. You can run multiple expert experiments in the same two-week window.

When I started consulting many years ago, everything was a three-month project with three check-ins. It’s steering committee number one, two and three at the end of the month, one, two and three. Now, everything’s in sprint mode. Everything’s tests, everything’s minimum viable increment. How do you move it on and adapt? I think it’s better and healthier because there’s a lot of time between a four-week readout and the next four-week readout and readouts the wrong mentality in and of itself.

It’s very similar to what the whole software development world went through, which is it used to be the whole waterfall model if you go back to the software world. It’s 3, 6, 12 months development cycle and then release a product. Your g business is going to die if you are operating in that mindset. That’s why the whole DevOps phenomenon came into play. The same thing has to happen in the go-to-market space.

It reminds me too of a study I read about pricing models. What they found is that the highest corporate valuations are tied with consumption-based pricing. It’s because you’re winning your customer every time they click a button. You can’t be asleep with a switch. There’s no hiding behind a three-year contract.

Going back to the whole product-led growth, you have to invest so much so that the user and the buyer see value in the product. That’s one. The second is switching from a monthly or annual to usage-based where you have skin in the game to ensure that the user is seeing value. Otherwise, they just pull the plug.

The head of our utility practice told me that we’ve already solved consumption-based pricing. It’s called your electric company. You get charged per kilowatt.

It’s been a fun conversation here, Jamie. Let me bring it to the finish line with a couple of questions here. What resources do you lean on to improve your skill? Is it community? Is it podcasts or books? Is it all of the above?

It’s going to sound bad, but I can’t read business books, books that should be pamphlets. I’ll read the abstracts and that’s fine. I come back to this human issue of business is not that hard. I had a CFO explain it to me once. He said it’s pretty simple. “In Zs need to be bigger than out Zs. You have profit leftover and everything’s happy.” I’m being a little bit tongue in cheek and certainly, I’m out there studying. I have the privilege of talking to so many companies and seeing so many models and have so many great peers that are out there seeing it.

For me, it’s about separating signal from noise and there are too many things to learn. The one that is the great unifier is people. “Why do people do what they do? How do you get them out of the bed every morning? How do you get them to change?” Culture eats strategy. All of this will succeed or fail quickly if you can do it in a way that resonates with people. That is where most of my study and my learning come from outside of the normal business channels.

B2B 29 | Go To Market
Go To Market: One of the luxuries we have as consultants is we get to come in with fresh eyes and a really good sense of what good looks like. We could say here’s how you might want to lay it out.


You can come up with all sorts of strategies, but if you can’t empower and motivate the people, it’s only going to take you so much. Again, it goes back to the two or three things that I reinforce and which I’ve seen play well is, first of all, having that intellectual humility and it’s critical. It’s not that you have answers for everything. That’s one. Second is having that curiosity.

You can conclude that your person on this team is thinking this way, but go and ask the question and the response will shock you. The third is going back to the other pillar in your study, which is coaching. If you have intellectual humility, if you have curiosity, which is gloved with empathy, that should drive you to become a better coach.

My mind was blown. I was talking to some friends and saying, “Here’s a situation. Here’s how I experienced it.” I said, “I read it in a totally different way.” I was like, “That is fascinating.” It reminded me that as humans, we’re always making up stories to make sense of the data around us. Those stories might be wrong or might be right and if you’re not curious, you won’t know.

One final question to you, Jamie, is if you were to roll back the clock and time and go back to day one of your go-to-market journeys, what advice would you give to the younger Jamie?

It’s exactly what you alluded to on this sprint mentality. The last living 3 months in the future, 6 months or 9 months in the future is more like, “What can we do tomorrow? What can we learn from that?” I started by telling you I went to Bain to do strategy and I thought about strategy as these big ornate edifices of intellectuals and they are but you don’t win with good strategy, you win with a good enough strategy and great execution. Tempering that short and long-term is so powerful.

Thank you so much for your time, Jamie. It was insightful. I got a lot of insightful actions. I told you that oftentimes, I pause the show episode and someone out there reads to it and comes back to me like a couple of months later saying, “This one piece is gold and this is what I applied.” Thank you so much for sharing all of your wisdom and stories.

Hopefully, there is a nugget in there for somebody. Thank you for having me. It’s been a lot of fun.


Important Links


About Jamie Cleghorn

B2B 29 | Go To MarketJamie Cleghorn is a partner in the Chicago office of Bain & Company. He is a member of Bain’s Technology and Customer practices. Jamie leads Bain’s B2B Commercial Excellence practice in the Americas, leads Bain’s GTM Transformation and Sales Play System℠ solutions globally and is one of the developers of the Elements of Value℠.

Jamie works with CEOs and executive teams during periods of transformational change, with a focus on strategy, growth and organizational effectiveness to achieve results. He has worked extensively with corporations and PE sponsors across technology, telecoms, industrials, healthcare and business services.


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B2B 28 | Customer Collaboration

B2B 28 | Customer Collaboration


Collaboration inside your team is expected in any thriving business. But what if you can extend that collaboration to your customers? When it comes to go-to-market sales, having a transparent collaboration with the buyer and the seller is a lifesaver. That is what Accord is doing. Vijay Damojipurapu talks about this with the CEO and co-founder of Accord, Ross Rich. Learn how Ross built a go-to-market playbook for his team and how he started Accord. Learn the challenges of building something new in the market and how to get market validation. Discover more about go-to-market sales and Accord today!

Listen to the podcast here


Accord And The Power Of Customer Collaboration With Ross Rich

I have with me Ross Rich, who is the Founder and CEO of Accord, Y Combinator Alum and in the go-to-market, MarTech, sales tech, customer support, customer success tech, and tech stack, depending on which lens you want to put on. That’s one of my favorite areas, which is the whole GTM tech stack. I’m super excited about your story, Ross. I’m sure we’ll dive a lot more, first of all, a very warm welcome to the show.

B2B 28 | Customer Collaboration
Customer Collaboration: Combining the challenge of building a repeatable sales process and working with customers transparently birthed a customer-facing collaboration platform for sales and onboarding.


Thank you for having me. I’m excited to dive in.

Again, I always start off with the signature question with all my guests because I want to deliver value to my audience first, which is how do you define go-to-market?

I was thinking about this before and it’s a tough question because it’s so much of a company now, especially if you have the product by growth. I think there are two answers. If you have your sales and marketing team and they sell someone, then they go into the product. I’d define it as the sales and marketing side.

As soon as you bridge both of those in and you think about retention and NRR and all of those great things, it’s the whole company outside of the R&D side of things. It’s a startup. It’s your entire company. If you have part of your product, that’s driving growth, which almost is true with any company now. It has to do with your retention and customer success. That’s how I like to think about it.

Especially for the PLG-focused companies like yours, you think about the product first, but then very quickly and importantly, you need to pivot to the customer and the user. Even for PLG strategy-focused companies, it depends. You need to focus on how do you quickly deliver value to your user first up. It’s user-focused. Buyer focused as well and how do you deliver. Hopefully, you get to a vitality effect and I repeat usability. All of this, again, comes back to that buyer and the user, knowing that person, he or her very well.

That’s part of your go-to-market. It’s the product of building everything.

It’s a huge part of the go-to-market. That is one core component. Again, I’ve listened to quite a few podcasts. I was listening to another podcast where it was the Founder and CEO of I think the company was Intellimize. His focus was all balling down to customer focus. The go-to-market strategy is sales lead but in your case, it’s a product lead go-to-market strategy. Would you agree with that?

The process is a bit of a mix. For Accord, in particular, it’s not self-serve freemium in terms of like, “You can go on. You get to set up and we’ll ring you up if you get past a certain limit like a Loom, Figma or something like that.” You get a free trial. You can play around. You can use the product before you decide to buy, which feels about right.

In 2021, the new company was starting out but you’re guided, assisted by an expert in the space that’s like, hopefully, a consultant and giving you best practices and what we’ve been learning to make you even more successful. It’s a mix of salespeople. It’s super helpful but that’s not how buyers want to buy. They don’t want to be led by a salesperson alone. They want to be assisted. How do you bridge both the need for people to play around with the product and validate themselves but also get that expertise and advice from someone who knows what they’re talking about?

It’s almost like it’s a salesperson but with a very customer success mindset and customer success-oriented. I’m sure we’ll dive a lot more during this interview. Next step, can you tell our audience and share with all of us your personal, professional journey, your story and what led you to what you do now and who do you serve?

I’m originally from Toronto, Ontario, Canada. I was born and raised in Canada. I went to school on the Westcoast on Vancouver Island and I studied business. My dream job after starting school there was to be in the music industry. I was managing artists. My brother and I started our first company together that was putting on events and bringing in artists that were touring across Canada in the US, hosting fundraisers. We’re very involved in the music and entertainment industry. Somehow got my dream job after school at Columbia Records. Working with artists like Calvin Harris, Snoop Dogg, Omi, Pharrell, etc., on album releases and songs and tours and all this stuff. That was the dream.

I quickly learned that wasn’t for me, long-term. I found the culture of the industry, but sadly, I didn’t see myself working in this industry for more years after the first year. It’s a lot of egos and the way of working. It was very bureaucratic. Surprisingly for such a creative industry. I ended up finding a job in San Francisco. I moved there before I had the job.

I did about 40 interviews with recruiters, screenings, looked up as the top early-stage companies and wanted to be at a company where I was going to be one of the first salespeople. I was like looking at sub 25-50 people companies exclusively and somehow, I ended up at Stripe. I don’t know how luck, etc. It was 2015 and they started to hire business and salespeople.

The first years were purely self-serve, selling to tiny startups, founders, SMBs, etc., adding on a sales team and luckily ended up being one of those first hires. That’s what drew me into tech sales and this whole idea of building repeatable go-to-market engines and the love of the deal. I did that for about five years then founded Accord with my brother a few years ago. That’s what brought me here. A secure, very random path from Canadian University and putting on events and concerts there to Columbia Records in LA and New York to Stripe, APIs, payments, and FinTech to a sales technology platform with Accord. That’s been my personal journey so far.

Find a group of smart people and learn and optimize from them. Money will follow. Click To Tweet

First of all, you’ve done a pretty good job summarizing your entire career in 2 or 3 minutes, so kudos to you on that but it’s amazing. You start off with something in the music industry, which is very creative. Of course, you can draw the lines and connect the dots from the music industry to sales. I get that part but then, what led you to sales in tech?

You don’t have many options when you’re a few years at a school and the only experience was music and you want to be in the professional space. I was like, “I’m good at working with people,” all that stuff even before the company that I had in university and at Columbia Records. I was like, “Maybe a junior sales role would be a good foot in the door.” For what I wanted, the opposite, I wanted a fast-moving company in the early stage to be able to be part of the strategy, which seemed to be the tech world. That’s what led me to focus on tech. The real reason I joined Stripe over the 39 other companies I had interviewed with was the team that I met there.

I was like, “This group of people seem insanely overqualified.” They’re incredible senior people and super talented folks from Google, Twitter, and all these other earliest stage companies. I was like, “You guys are joining this small startup that I never heard of before and all that stuff and selling APIs and FinTech?” It wasn’t proven out at that time yet. I was like, “I need to be around this group of people.

I’m going to learn so much and it seems like a great time and opportunity to do this.” Within a few weeks, a couple of months, I was hooked. I’m like, “This is what I’m going to do for the next X number of years.” That’s what led me to join Stripe. It wasn’t as thoughtful as you think, I looked at the market, what’s going to be growing and fitting in tech, whatever APIs and the decentralization of all this stuff, I was like, “This is the most amazing group of people that I’ve spoken with and met with. This is the right shift to be on.”

For all our audience, I think the key takeaway, don’t overthink. There are 1 or 2 points that Ross mentioned. One is the group of people, team, smart people, a top tier, and the cream. Look at the opportunity of working with them, being with them, and learning as a team.

Optimized for learning. That’s what I optimized for and led me in the right direction.

Once you optimize for these tools, money will follow and that’s what led you to study your own. Prior to that, I think you applied for the Y Combinator.

We got into YC then we started the Accord.

Tell me a story around what got you into thinking around the pain point? You’ve been doing sales. You’ve done fantastically well for yourself but what was the transition and shift from being an employee, nothing wrong with that, in sales to, “There is a bigger problem I want to solve. I want to start a company around this?”

Honestly, it’s pretty organic starting Accord from my time at Stripe. There are two main things that I had on the top of my mind that I was very passionate about at Stripe. One was, going from being one of the first sales and business hires to a massive 400 global sit person sales team and doing the deals myself. From the team perspective, the challenge was always we’d break into a new market, new product, etc., how do you get everyone else that we’re going to bring on to understand what that motion looks like? We went through all the repetitions, all the loss deals, the learnings, the million conversations. How do you get that in that process to the rest of the folks? That was a big challenge.

I was one of the leading reps there and we’d work on the new segment or the new product. I found it so challenging. There was never a great solution. Testing out Google Docs, Confluence sheets, bringing in trainers or the classic old-school laminates and bringing in all that stuff. It’s never been an effective way for other folks to understand what the process should look like, what meetings you should have, what resources you should share when, what stakeholders you should loop in at different parts of the team, and what expectations you should be setting. These details make a difference that every new rap has to learn. That was one side of it. These building of go-to-market playbooks and how to effectively work with customers throughout the buyer journey.

B2B 28 | Customer Collaboration
Customer Collaboration: Accord is a collaboration platform for B2B sales. It’s a shared plan of steps and milestones that make it really easy for everyone involved to understand what the deal is, in a very transparent setting.


The second one was the collaboration with customers. I’d hacked together this system that I built. This operating system of like shared slack channels and Google Docs and sheets and presentations and templates and emails. It was an effective way of being very transparent. I collaborated with my customers through all these shared workspaces, but it felt very like a one-off and across a lot of different things. It felt like there should be a solution, software for this, whether there is JIRA internally for a lot of the product teams.

There’s Figma for design and GitHub for engineering. Why is there something for such a collaborative organization which has sales? There’s nothing for that internally as well as externally with the customer. We’re combining both of those. The challenge of building this repeatable sales process as well as working with customers transparently birth the idea of Accord, which is a customer-facing collaboration platform for sales and onboarding.

There should be something that is templatized that everyone can use and customize from there. There should be something that is collaborative with customers. Again, it wasn’t like sitting in and how do I think it started ideas. I was like, “What am I doing? What are the challenges that I’ve run into? What do I think would be helpful for the next person in my position?”

I think the key point for all the audience is as much as you want to create your own company but that will not and should not be the driving force. You can have that in the back of your mind but unwind and let the problem percolate. Let that see thought grow into something bigger. That’s what I see in yours. It’s not that, “I’m at Stripe. I’m doing well.”

It’s not about arrogance that, “I’m the best in the world. I’m going to create a company.” It’s not that attitude at all versus there’s a playbook. There’s a bigger gap in the space, specifically around the sales organization and the buyers. Now, why is that more of a vendor buyer relationship versus a partner relationship?

That’s a good point. I think, similarly, I’d add like, what is your passion? That’s the thing you’re going to be most successful at. Say you do want to start a company and that’s the thing that you want to do next. It’s not going to be looking at the market. As an investor, I don’t think it’s going to be looking at it as a human and what you are most passionate about.

That’s the thing that you’re going to be most curious about and have a unique perspective on to solve problems for people than necessarily like, “This space is hot now. I could make a lot of money off this type of business model.” Everyone is thinking like that. That’s not going to be the unique next insight that you have as a person. It’s going to be from what you’re passionate about.

Look at your market not as an investor, but as a human. Your insight as a person is going to be from what you're passionate about. Click To Tweet

Let’s switch gears and more on the lighter side of things. You guys are unique in the sense. It’s you and your brother who started this company. It’s not that often and not that a common theme. How do your parents deal with that or tell others as to what you guys do?

I think my dad deeply understands this because he was an entrepreneur but a salesperson at heart. He made sales for fifteen years before starting his company. He works with clients every day and understands, although they didn’t have collaborative workspaces but the importance of building those relationships, collaboration, and transparency to create the best partnerships. How would they describe it? To most of their friends, they’d be like, “Our kids are doing some tech thing. A technology company that’s helping salespeople do stuff.”

I’m thinking of different ways we can go here. One is, how did you decide between you and your brother as to who will be the CEO and the CTO? Let’s go down that path. How did you guys figure that out?

It was pretty organic. When we were making music back in the day, I felt the natural roles. My brother is, I would say, much more creative than me. He was always doing the music production, the recording stuff, all those pieces and had more of a product and engineering mind than myself. I was more of the external marketing and all that stuff. When it came to starting Accord and we started working on it together, he naturally started to think about it like, “What is this thing going to look like?”

He’s designing it and thinking more about the product side. I feel like I was more of the like, “We have a hundred conversations with sales reps, CEOs, CROs, VPs of sales, etc., what their feedback is going to be?” It’s an organic partnership. He was starting to build out the wireframes, the mock-ups and prototypes. I was out there trying to understand the market. That developed pretty organically into I was the external Rich brother and he was the internal Rich brother in terms of working with the R&D team. I was out there talking to the first customers and recruiting. That’s how it pretty organically happened.

It is only you as the cofounders or did you have anyone else?

We have another cofounder. We wouldn’t be here without him, Wayne Pan. He’s our CTO. My brother is CPO. He is a multi-time founder, amazing engineer leader, led teams of up 30 to 40 engineer people. Also led product design engineering orgs. It’s like the whole R&D org, a very holistic perspective on that. Similar to what we were talking about, the go-to-market side on sales and marketing. He’s started a couple of other companies before. One that was invested in by Sequoia that sold to LinkedIn.

He’s been in a lot of ways the shepherd for us on our first founding journey, loves to build teams and the operating system of a company and that foundation, which I feel like a lot of times with younger, early first time CEOs like myself and my brother is some of the biggest complaints from employees and other stuff is like, “How do you do this? What is the foundation? What does the start of the week look like and the wrap-ups and the quarterly kickoffs and retros?” He’s super thoughtful about all of those pieces of the company, culture and team building, which has been super awesome to have.

I think that’s a core component, especially when you are building the team and doing fundraising early on. With one founder, it’s super tough. It’s not that it can’t be done. If you go onto the other extreme, which is 4, 5, cofounders, that’s a big no. Kudos to you and your brother for identifying someone who’s stronger on the product and the engineering side. Now, did you guys and Wayne work together earlier or how did you guys come to know each other?

It was crazy. It was an intro from one of our first pre-seed investors. He’s one of the first people that say, “Commit money to their crazy idea that was Accord.” Bob Ross was leading Stripe’s partnerships team when I met him. Both of their companies, at some point, were acquired by LinkedIn and happened to overlap there. When I asked Bob, “Whom do you know?” It was like, “I happened to catch up with Wayne. It was super random. We were having caught up in years and it was perfect timing.”

From the first conversation to decide to work together, it must have been single-digit business days for such a huge decision. It felt super right. I think personalities melded well and the vision of the culture and type of company we want to build. One of the first things that Wayne said when I was talking to him. I’m asking how he thought about the company building, etc. It was the quote from Steve Jobs around, “Hire smart people, get out of their way and empowering people.” It was like that. I feel like a few people live that and that’s the type of team we try to build.

Have you heard of this book or read this book, Think and Grow Rich by Napoleon Hill?

Of course.

I would be surprised if you said, “I don’t know that.” It’s almost like that but then something is strong. The universe conspires to make it happen. It’s exactly that. Enough of the loosey-goosey and gooey stuff.

We were talking about manifesting the company. It’s funny that you bring that up. We manifested it.

Let’s talk about Accord. Tell me about your product. Whom do you serve, how you build the business, where you guys are at now?

B2B 28 | Customer Collaboration
Customer Collaboration: When starting a startup, you can be an expert in this space for years. But if you’re launching a new type of product, you’re not going to know if you’re successful until it comes back from the market.


It’s super high-level to summarize. First, it was a customer-facing collaboration platform for B2B sales, onboarding and success. The core of it is if you’ve heard of mutual action plans before in sales, a shared plan of next steps, timelines, and milestones. We add in resources, team members, a summary of the deal to make it easy for everyone involved in both the buying and the selling side to understand what the deal is, very transparently setting the right expectations across the board. That’s the idea. We mainly work with high-growth startups.

We’re working with some seed and series a company all the way to the likes of Figma. We work with their enterprise sales team closely. Across the gamut, I would say that where we help companies most are in the high touch, multi-stakeholder, project management side of the deal when you have a lot of people coming in. Maybe it’s a product, engineering, design, and finance decision-makers. You need to keep everyone in the loop around pre-sales with maybe it’s risk or compliance or legal and all that stuff.

Post-sales is like, “What does it look like to roll this out across the company successfully? How do you build a repeatable motion around both of that pre-sales and onboarding?” Make sure there are smooth handoffs and setting the right expectation for your customer. That’s the area that we play in to start focusing on technology companies who are the early adopters of new tech like Accord.

I’m super excited about what you guys are doing. Think of it this way. You got collaborative platforms internally. Now, we are doing that for an external audience that’s specifically for sales and buyers.

Everyone knows how helpful Asana is and Monday.com and Click. All of these things have been wildly successful notions for years but there’s nothing that’s built to work externally with partners, customers, buyers, and all that stuff.

Talk to us about the go-to-market. You did mention high-growth scale-up startups. Are you looking at geographies? Are you looking at what tickles and what is the go-to-market motion like?

It’s been evolving. The thing that I was familiar with was more of a top-down, mid-market, and upper mid-market enterprise deal from my time at Stripe. I know at the end of it, I was working on 1 or 2 deals across months. I knew that motion and made sense for something like Stripe because you’re ripping out your entire revenue engine and you’re putting in Stripes.

For deals like that, it’s not like you’re going to do 5% of your payments. All the work gets done and you shift over, which is very different from something like Accord, where you could have a sales rep or a manager bring this in a small part of the organization and test out on one deal or one segment and all that stuff.

I’ve had to learn a lot about product-led growth and understanding how our buyers want to buy. It’s been super organic in terms of how we’ve thought about and matured our go-to-market motion. To start, it was me talking to anyone in my network about this idea and the curious conversations turn into your first users. That’s how it started with the first 5 to 10 users. It’s talking to people and asking for friends of friends who would be interested in this.

It is similar to fundraising. It’s the same thing with the customers, friends, and family first, then go wider.

It started there and when we started getting into the public and beyond that network was February 2020. It’s when we did our seed raise announcement, which went on TechCrunch and got a great reach there. It was interesting because we first moved from us going to certain people and our assumptions to what is going to come back from the market. You send it out into the world.

Who are the people that this is going to resonate with? It was interesting because it wasn’t only the people, sales leaders, VPs of sales, and CEOs. It was a lot of sales reps, managers, and even smaller seed series A-company mainly selling to a series of B2C above. It was like, “There is this interest from not necessarily would be a top-down sell,” but some people that want to click around more on the product.

What we did is we shifted in the next few months to a free trial motion and messaging more for these earlier stages like series A, high growth. When you’re going from your first 3 to 5 reps to 10, 20 to 50, how do you make sure you have the right motion to scale? That seemed to be a great point. Before you had all these systems in place, harder to rip out something than to start with something like Accord, that’s where we shifted to, had way more interest in terms of the click-through rate of the website from request to demo to starting with the free trial and giving someone the custom workspace.

The curious conversations turn into your first users. Click To Tweet

We’re even looking to double down on that thing about what’s an individual plan that people can start with. It’s been from the full top-down to the free trial sale to even looking at other ways of getting the product in people’s hands with less friction and thinking about how does this specific type of person in this market at the stage company in this role want to evaluate and thinking through that lens.

That is exciting. I think it goes back to when you got your earlier hypotheses or experiences you went to top-down and thanks to the seed round, the press coverage, and everything else. You’ve got good publicity, good coverage, and that led to outreach from the market to you guys.

When people ask my biggest learning, that’s been my biggest learning of starting a company. Startups are you can have your hypothesis. You can be an expert in this space for years. If it’s a new type of product and a new category, you’re not going to know until it comes back from the market to go to your assumptions. Having opportunities like that and for our GA launch and through product time, we got another set of that and refined it. You’re only going to be successful. If you think about it in terms of the market first, not product first or the sales process first, that’s the biggest learning from this experience so far.

It’s amazing. It’s all first principles and foundation, but unless you go through it, you won’t know how to apply it and you’ll make the early mistakes.

That is one thing. That’s why they say, “Launch quick.” It’s not like, “Get the product out there and start selling quickly.” It’s getting into the market and start to get those data points back to you as early as possible. You’re going to go down, building the wrong thing or a muscle around certain processes that aren’t going to be the things that get you to success.

You might get that initial traction but how do you know that this is your time? It is for the next 1 to 2 years.

You don’t know. I think that’s the answer to all this stuff and why it’s so challenging. It’s so much instinct. You need to be able to be wrong and be nimble. That’s also one of the biggest learnings. You went out and it was this growth. You were focused on these later-stage growth companies. You were getting this feedback back with a ton of interest.

They’re doing evaluations. These are the blockers and we do this a lot and go, “This seems a lot easier. Maybe it’s not right. Let’s test it out. We did both of them for a quarter.” It was like, “This is where we’re winning. This is we’re getting the most usage. We have to double down at some point. Let’s make another big bet on this.”

If in 3 to 6 months, that’s wrong, let’s make sure we’re thinking holistically but that’s the stop and start. You need to be doing things a lot and heads down but then you need to come in. That balance is the right way because we could have been wrong about the adjustment. It could have been like, “Only because it’s TechCrunch.” That was the readership you saw along from there. It could have been wrong and you should have continued going after this other market, but you don’t know.

Let’s double down. I’ll put you in a somewhat uncomfortable spot over here, which is, based on this initial data, you need to make hiring decisions. For example, let’s say you’re building out a marketing team. You say, “This is the segment I’m going to go after. This is a go-to-market and this is the 1 to 3-person marketing team. Now, are you going down that path? How are you thinking about building your marketing, which is a core component of go-to-market?

We took a different approach there. We spent so much time the first year plus building out the product. We’re working super closely with customers instead of going out there and building up the team and spending. We had my brother, who was our CPO shift to for the first X number of months to marketing because he was the expert and the salesperson. Of doing that, it was like, “Someone with more intuition on this to figure that out.” That was super key to us getting those data points back and being able to do it super quickly. It didn’t have to go out and put together a JD, interview all the candidates, and get them to ramp up on everything that we’ve done.

That would have been the time that it took us to run those experiments. It confirmed that market. You need to be sure about that before you start scaling. We took a very similar approach to the sales team. I wish we had one person but when we did the launch in February 2020 with the seed announcement, we were inundated with these conversations.

It was myself and my colleague, Danny, who was doing everything at the time, CS operations, sales, etc. Everyone needed to jump on calls. We had our engineers, Wayne and Ryan. Everyone is jumping on these calls. I’m glad that we could get those early learnings in first before we understood who’s the right marketing team and sales team to start building, then we doubled down.

We hired our first two folks that were more experienced generalists who could also help figure it out. We didn’t look at like, “Let’s bring on five people to do this.” It’s like, “Let’s bring on two other people to help us continue to figure this out, and then two other people can sell them, then you bring on the next 5 to 10 people.” That’s how we’ve approached the team-building side of go-to-market.

That makes total sense, especially in that high growth early stage where you guys are at. It’s all hands on deck. You need to shift across roles. You might be engineered formally but you need to jump in marketing, sales or even customer success. It doesn’t matter once you’ve seen that play out in 3 to 6 months. Now, “This is a time when we need to hire someone full-time for that role.”

B2B 28 | Customer Collaboration
Customer Collaboration: When it comes to budgeting, make sure you’re nailing your positioning and messaging. Experiment around that before accelerating the spend. Focus on the right things that matter first.


I think that’s the right way because people discount how much work it is to go out and hire properly. First, understand the role. That’s something that I’ve learned too. We probably spend the first month, 2 to 3 weeks at least to understanding the role. Having 10 to 20 conversations with people that are experts there like, “What level they should be? What background should they be? What’s the interview loop look like?”

You’re not going to get the best person in there unless you can speak their language or you understand what you’re looking for and what they would do then. It’s the hiring, the great loop, making sure you’re not cutting corners and it’s onboarding them. As you said, having someone do that for a few months and making sure you understand what you need to do next prevents you from making a lot of mistakes down the road.

How do you think about the budget? I don’t want you to reveal exact numbers but ballpark percentages, especially bare yard in terms of growth. We all know benchmarks. They typically say like 10% to 20%, especially for marketing. In sales, it’s more mostly headcount. How are you thinking around those for the marketing budget?

Our thoughts on early marketing have been very similar to all the same framework that we’ve used for every other piece of the business. It has been making sure we nail the positioning, messaging and experiment around that before accelerating the spend. That’s playing to a lot of the organic stuff. You can tell from what you post on LinkedIn, go to your newsletter or later test on persona. Even outbound is a great way to get the feedback back quickly. Make sure you’re focusing on the right stuff, so when you spend $10,000, $20,000, $30,000 a month, you’re sure that’s the approach that we’ve taken. We’re starting to ramp our first ad spend.

We spent a lot more time on thinking about what is exactly the problem we’re solving, how do they think about it now, what are the keywords, the percent, all of that stuff. Again, taking that approach to things, then hopefully we feel very comfortable putting in a ton of money and it’s efficient coming back. When are you ever going to catch up on that? You can see it as a business. As soon as you start hiring multiple people and have them spend and start getting those leads in, you’re never going to go back and foundationally fix things. You start growing too fast and there are more people and more processes. Taking that extra 20% to 30% time pays off in terms of building a very efficient go-to-market.

Again, it goes back to reinforcement, which is, first of all, you do things that won’t scale. It’s called counter-intuitive. You need to do things that won’t scale. First, you get your formula right, then you can pump in the money.

You’re never going to start doing things that scale to figure it out to experiment.

Another controversial topic in the industry, which is around SDRs. Whom do they report to and why? Is it marketing or sales?

Market first, not product first. Click To Tweet

Foundationally, I don’t know. I haven’t spent much time thinking about it because I didn’t have to. One of the first salespeople we brought in had been building out for many years, full-cycle sales, SDR teams from outbound to close. We brought in a demand generation marketing lead who has never run SDR teams. Maybe longer term at Accord that changes but for this small team that we have now, it’s very clear you gave that function to the person that’s done it successfully for many years and you figure it out later. If I had to say, honestly, philosophically, it feels closer to marketing than sales because it’s tough and stay. It depends on how you think about the SDR role.

If an SDR role is slowly generating demand, I think this has to do with a lot of the average contract value of the company. If it’s very big business, you’re trying to break into accounts. You’re maybe pairing them up with an account executive. That feels like more of marketing. You’re starting the conversation, whereas if it’s maybe a lower HCV and they can help close the deal or get it further because that’s the type of product and sales motion, it feels like more sales. It depends on the type of product and sale it is.

Again, I would say if they can contribute more to the deal and can have that conversation and it’s like less of an enterprise, like a twelve-month thing. I hate handoffs. I hate as a buyer. As a seller, I hate handed off, the missing context, all that stuff. I’d rather have them go full cycle but you can’t do that if you’re trying to get into a $500,000 to $1 million deal. You can’t afford to have SDRs make that motion. I’m curious to hear your thoughts on that, though.

I think being pragmatic is one thing. It also depends on the personnel that you have on your team. In your case, you have the sales leader who’s run the SDR team. You give it to that person compared with imagining who has minimal experience. I get that practical, pragmatic piece. There is the other piece, which is more of a mindset starting with the leadership, which is how are you seeing SDRs or BDRs? Again, it all goes back to how are you serving your buyer the best way? Are SDRs or the BDRs? First of all, is it outbound or inbound? We start with that. That’s the first thing. Do they handle outbound?

I’m assuming this is all outbound SDR.

That’s one thing. The second is, are they more into an appointment setting mindset, which means, “I need to give so many meetings, many leads, SQLs even MQLs. It doesn’t matter.” That’s a whole different discussion but how many meetings do I need to give it to my account executive team? That’s very short-term thinking. Again, it’s more of. It’s me versus what’s right for the buyer.

I would say, of course, there are a lot of variables around contract and sales cycle. Honestly and sincerely for me, especially that I’ve run marketing teams, I believe that it should be within marketing where that handoff is happening and only then, it’s almost vetted out to a discovery phase, then you pass it to a context. Get us to take it forward through, is there a good fit for getting into a contract discussion then the close? That’s only me.

My only issue with that is I’m picturing myself as a customer. If it’s outbound, I have that conversation. I do discover then I’m talking to someone. It’s like, “What about that context?” It’s less efficient to have maybe a join and to jump in there or even to tag-team it. If I’m the customer, I want to make sure that the context is carried forward. Maybe you can solve that with a very smooth handoff somehow. I haven’t experienced that as a buyer ever, but that’s my personal perspective.

My philosophy and how I approach marketing are in absolute alignment with sales. Again, it goes back to the buyer experience. If we do have SDR supporting into marketing, SDR is responsible for the buyer experience. He or she has to work with the account executive. It’s not like, “I’m done now. It’s your job. Throw it across the wall.” That should not be the mindset at all.

I agree. I guess we haven’t worked together. Maybe if we had worked together, I’d feel differently.

Folks have worked great, let’s say the sales leaders. They all attest to the fact that I am someone who gets and who believes in the alignment piece versus typically marketing sales is at loggerheads.

That was one of the biggest things when we were hiring our first marketer. That was one of the biggest things we’re testing for and the first conversation with after my screen with our sales leader because it was so important to find someone. Especially so early on, it’s not like you’re building your thing. It’s like there’s nothing that exists. You can build it together. I’m proud of how I’m seeing. The closest partnership is between them now. I’m seeing on the go-to-market market team, which is great.

B2B 28 | Customer Collaboration
Customer Collaboration: One thing that’s really important from the sales go-to-market motion, is the efficiency of enabling individual reps and managers to start using your product before you sell to a team.


One final question within this whole 2021-2022, then we’ll go into the last section, which is, you want to create a category. Pretty much talk to any founder. They want to create a category but it’s not in our hands. Again, it goes back to what is the market saying? If you were to talk to your marketing and sales, what would you say? Tell them that, “This is working.”

What will be the 1, 2, 3 objectives for 2022? How will you approach your whole category creation playbook? By the way, I’ve seen the resources that you have put together. For me, I’ve done research around the winning CMOs. I think I mentioned this to you, which is around content. It’s around the community and experiences/events. It’s these three things. The winning good market leaders do this extremely well in sequence. Not that they’re spreading themselves thin. How will you apply or how are you thinking broadly? I gave you some pointers and some time to think about that answer.

One thing that’s important from the sales go-to-market motion, I think, is the efficiency around having both this way of enabling individual reps and managers and earlier stage founders to start using Accord. Before, we necessarily like to have a sale to a team combining that with efficiency and selling into those companies and making that bet super early on in 2022. As a company to pay off, not even maybe in 2022 but the following year and the year after, you’ve seen a number of companies do this super well. That’s a key part of the strategy. Moving forward is that big bet in terms of mixing that bottoms up and figuring out what the top-down is for larger companies.

Both how do we go even lower and have that motion, which is going to be more marketing product-led as well as build our muscle around that more larger growth deal and selling into those multi-stakeholders? It’s sales enablement, ops, managers, executive sponsors, the reps that are saying, “Okay.” Those are two big pieces.

The other piece is what you’re referring to, which is how we are seen as the thought leader when it comes to building repeatable sales and onboarding processes for early-stage companies? How is Accord the answer for when you think about other companies like Stripes, FinTech and API but they’re thought of as the best practices in terms of the engine is the most developer-friendly tool?

Again, Accord is a collaborative workspace between buyers and sellers, but how are we seen as the people that best understand how to solve this? That’s why the CEOs, VPs of Sales or other people come to us is like, “They’re going to help me solve this problem.” This is the solution but they’re thinking from the problem first. That core problem is ubiquitous across every B2B company. Those are some of the key things that I think about overall for 2022. How do we do that? Probably a variety of different ways.

Again, it goes back to there are things that you can measure and you cannot measure. This is one of those things. You want the market to perceive you in such a way. You can do surveys, brand recall experiments, statement, recall experiments or problem statement recall experiments and who do they associate, bet around those things. It’s a great area. That’s something that I’m trying to wrap my head around as well, which is category creation. Every founder wants that but how do you know that you’re creating a category?

It’s an interesting question. I love the book Play Bigger. That’s about category creation, if you’ve read that.

I’m reading that. That’s my nighttime reading book. We can go again multiple ways but I did tell you and mentioned that we’re going to close. You have been pretty patient over here and I’m also respectful of your time, Ross. The last couple of questions to you is, whom do you lean on or what resources do you lean on? Is it community? Is it maybe investors or PR founders? You’ve got the Y Combinator community, for sure. Is it podcasts? Is it books? What do you lean on to get ideas?

I would probably say that first and foremost is my intense routine. I’m a very routine-driven person and make sure I can sometimes get out of whack with that, but I think I’m functioning best when I’m getting up and going to bed at the same time. When I’m going to bed, I’m putting away my phone a couple of hours before, reading, journaling, getting up and doing a run with my dog and a workout and yoga and all that stuff. That’s the number one support system and routine that I built-in. Again sometimes, life and things get busy. It’s like, “This week is going to be a tough one and I have to put it down for a second,” but I always regret that.

You need to be able to be wrong and be nimble. Click To Tweet

Outside of that, I’ve tried to build a community of folks that have been in my shoes before. I don’t want to sound arrogant or anything but it’s a unique pressure more than I thought it would be to feel responsible for the success of a company, employees, investors and chatting. I have a handful of folks that have started companies and now advise or invest and all that stuff. I meet a lot of them on a bi-weekly basis to feel heard, feel supported and understood. It helps with that perspective of, “This is where you’ve been, this is where you’re going, and these are the things that are going well.” To bring that perspective when all you’re thinking about is this one thing and the most important thing that day or the week. That’s been hugely helpful, and my dog.

I love the fact that you call out routines and having that very strongly, again, to share my personal and what I do on a personal basis. That’s almost like me. I’m a very routine-driven person to the fact or to the extent that my family and my wife will say, “You’re very rigid, not being flexible.” There is a reason why I’m being rigid so that everything else can work. The same thing with running, again, as you said. It’s getting those things done first. Take care of yourself, so you can start taking care of the bigger things and take care of others. Do you listen to any podcasts during your run or is you and your dog?

I try not to bring the phone with me or anything. It’s the morning silence.

One final question to you is, if you were to turn back the clock, in your case, it would be day one at Stripe when you were in the GTM role, which is as a sales rep. What advice would you give the younger Ross?

I feel like I’m a very serious person and very focused. I think, enjoy it more with others and sometimes take that break. I had some good friends that helped me do that sometimes but doing that a bit more is probably the advice I’d give to myself.

On that note, thank you so much, Ross. It’s been a pleasure. I’m going to root it and I’m sure our community is going to root for your team. I call it a success and wish you the very best.

I appreciate that.

Thank you.


 Important Links


About Ross Rich

B2B 28 | Customer CollaborationCurrently building inAccord.com to move B2B sales from Vendorship -> Partnership 🤗

SF based, Canada raised 🇨🇦

Outside of work, I love to:
– Ski Tahoe, hike Marin, & play/coach soccer
– Explore meditation, yoga & mindfulness
– Adventure through new countries & cultures

Inspiring Reads:
– The Alchemist
– The Book of Joy
– A Short History of Nearly Everything
– Abundance
– The Making of the Atomic Bomb
– Siddhartha
– Creativity Inc.
– Losing My Virginity
– Man’s Search for Meaning
– Napoleon (Andrew Roberts)


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Maintaining customer focus should always be one of your top priorities in B2B. You must know the people you are serving to no matter what business you are in. In this episode, Vijay Damojipurapu is joined by Ravi Pendekanti, the SVP of Product Management and Marketing at Western Digital. Ravi shares how they achieved B2B success with customer-centric tactics focused on listening to the needs of the market. He also breaks down how businesses should craft customer-focused strategies and the amazing benefits of doing so. Plus, Ravi shares the exciting projects they’re working on at Western Digital and the role of big data in the upcoming years. Tune in for an insightful and informative discussion about managing and improving your go-to-market strategies!

Listen to the podcast here


Ravi Pendekanti On Why Customer Focus Is Vital In B2B Go-To-Markets

Welcome to yet another episode of the show. I’m excited to have Ravi Pendekanti, who is the SVP of Product Management and Marketing at Western Digital. Welcome to the show, Ravi. I’m excited to have you.

Thanks, Vijay. It’s great to be here.

I’m super excited. I’ve known you over the years, both on the professional side for a couple of years. Our careers overlapped at Juniper. More than that, I’ve known you as a person on a personal basis for many years. What stands out for me is as an educator on the professional side, you had a very awesome skyrocketing career, which I always look up to for inspiration, but at the same time, on the personal side, I enjoy your company, sense of humor, being yourself, and bringing everyone into the fold. I see based on what I’ve studied and researched on you, it’s the same qualities that you bring at work as well.

We do. You have to. Otherwise, you can’t enjoy your day-to-day life. The more we are who we are, the easier it becomes to go get our things done.

Let me start off with the signature question, which I always ask all my guests. How do you define go-to-market?

For me, go-to-market truly is four major pillars. You can’t do any go-to-market strategy, planning, or execution without addressing these four fundamental elements. 1) You have to understand the market. Understanding the market landscape is crucial, which means you need to know what’s going on in the market and who the competition is. 2) One has to do segmentation of the market. 3) You have to go out and get the right messaging. As a marketer myself, it’s never lost on me that without proper messaging, you probably are not going to reach your target audience.

Finally, you have to work on the right distribution strategy. How are you going to get your product to where it should be? Are you going to use the direct sales force or partner community to get there? Even if you look at the partner community, you are going to have resellers or go with their distribution staff. There’s a whole rhythm of other things that one has to work through, which becomes important. It’s those four elements that, for me, constitute a good go-to-market strategy/execution policy.

You covered the key aspects, which start from the first and foremost, which are the external deal and the market understanding. You talked about the segmentation and the classic STP, Targeting and Positioning, but you also added on the more important and critical piece. You’ve done the research, segmentation, positioning, and messaging. Now, how do you get that message out to the relevant audience and right segments at the right place? It’s end-to-end.

I completely agree. I’m obviously aligned on that, but let me put you and drill you into some more aspects. That’s an external view and then there’s an internal view within the company, which is top and foremost the alignment across product, marketing, and sales. Depending on the type of business, if you are SaaS, you’ll have support but customer success as well. How do you work on those elements? Once you’ve done the external study, how do you align internally?

The more we are who we are, the easier it becomes to go get our things done. Click To Tweet

You do them in parallel. You cannot afford to look at the external elements without working on things that you need to align with the various functional organizations within your own company. You’ve got to run a parallel effort. The other way I also look at this is to do all this as much as we might think we are in the technology space. First and foremost, we are in the P2P business, which is a people-to-people business. None of this gets done if you don’t get people excited internally as well to believe in what you’re trying to do.

What that might mean is you have to go ahead and build your bridges with the engineering team so that the product can build in time, making sure that you’ve got the right feature functionality. You probably have to work with making sure that you’ve got all the sales elements in motion and the training elements to be looked at. There’s a whole rhythm of other things that one has to do.

As you do this, the benefit is not just making sure that everything is well-oiled machinery or becomes one, but more importantly, as you do this, people are going to be more open to leaning in and giving you ideas and suggestions so that this can is in the game now, which will help you get to market better and faster maybe too. I would encourage everyone to do that both the external things we talked about, whether it’s gathering the market data and competitive data, but not forgetting to do all the things you got to do as you’ve been called out internally in a parallel fashion.

That perspective is lost on a lot of marketers. Not just marketers, even for a lot of folks within the go-to-market functions across the board. Especially in the B2B world, it’s business-to-business, but a lot of folks, not intentionally, but it’s just that this one that they have a narrower perspective out of various reasons.

The part that you mentioned is lost. At the end of the day, even if it’s business-to-business, it’s still person-to-person. It doesn’t matter. Something that I’m seeing, especially the leading B2B organizations and B2B marketing teams are doing very well, the names that come to my mind are Drift and Gong. There are quite a few others that are doing extremely well and they have had unicorn valuations a lot more.

What they’re doing is they’re bringing in the B2C, business-to-consumer go-to-market motions, which is a deep understanding of the consumer and then delivering those messages. It’s almost shifting their mindset into, “Look at us or understand us because of who we are and more importantly, less of us, but it’s more of what you are and who you are.” It’s bringing that element. B2C elements into the B2B world, I’m seeing a lot of that being done.

It’s important for us to go and make sure that we do that too because some of the attributes of B2B play out at B2C. As we’ve already accentuated the point, at the end of the day, we are a people-to-people business. That means that you’ve got to go take care of that as well. We should only help you go meet some of the other elements of your goals as an organization.

I would love to drill into more aspects as we go along in this conversation. Shifting onto the lighter side of things, how do your kids view, tell, or describe what you do at work?

B2B 27 | Customer Focus
Customer Focus: Some of the attributes of B2B play out at B2C. At the end of the day, we are a people-to-people business.


This is interesting because my dad, frankly, for a number of years, always thought I was a sales guy. In some ways, he still thinks I’m selling, though I keep telling him, “Dad, my job is not sales. My job is to try and understand where the market is headed and then try to come up with the right product ideas and then help create the right messaging and help our sales guys to do what they’re supposed to do, but not necessarily as a salesperson.” That’s always been a constant education to my own dad. He seems to understand, but then he falls back and says, “No, it’s more like a sales job,” but I’ll keep trying.

I’ll credit your dad, though. The main thing is he is right because we are in the business of selling. It doesn’t matter, but you are selling your ideas, your vision, and the direction that you want others to go to. You may not have the formal title of a salesman, but he is right.

It’s interesting you say that. In fact, his pet peeve is that each one of us is a salesperson and I would ask him, “Why do you say that?” He said, “Think about it.” I went, “Let’s say when my kids were young, they didn’t want to take their glass of milk in the morning or eat their veggies. I was selling to them and enticing them with something, whether it was an extra hour of TV time or getting them some candy.”

His no-hold emotion is, “You are a sales guy.” In fact, he would say, “All of us are selling. Whether it is trying to get your family to go out with you and they probably have other ideas, you’re selling.” He is a wise man. No wonder he was one of my mentors for sure and continues to be doing so, but in a way, we’re all selling every single day.

I can see your wife jumping up and down when you called out and told, “I incentive your kids with extra TV time and candies.” I’ve been impressed and inspired by your amazing career growth. Can you share with our readers and talk to us about your transition all the way from early days, but more importantly, the inflection points, how do you transition, who do you serve now, and what got you here now?

There are a couple of things. I still recall I started off my career as a hardcore engineer. As the saying goes, I had a choice given by my parents, “You could choose to be an engineer or a doctor. It’s fantastic set of choices.” Most people from the Indian subcontinent could relate to it and the choices would be those two typically. Of course, I would sign up and I said, “I’ll go be an engineer.”

I was a hardcore engineer for the first few years of my career, but then I realized that there was one situation that occurred wherein one of the companies I was working for happened to be Compuware. They had a customer who had an issue. At that point in time, the GM then decided to send me to go see if I could figure out what the issue was and fix it. That was my first interaction with a customer directly because I was in the back end all the time before that.

It turned out that I enjoyed the interaction with a customer because I was sitting down and trying to figure out what exactly transpired and what kind of data had been collected to try and understand what the issue was and then subsequently try and see how it can be fixed. During that process, I realized that I enjoyed what that interaction was. Due to the interaction, I also got to understand that there are some features that we didn’t have, which I took back to the engineering team and said, “Here are the things that need to be done and this is what I learned.”

If somebody else has learned and they can help propel your learning that much faster and further, why not leverage it? There's no reason to reinvent the wheel. Click To Tweet

At that point in time, I recall the engineering guys telling me, “This is great feedback, but it’s not us you should give the feedback to. You should send it to product management.” I still recall I said, “Product management, what the heck was that?” I never knew the existence of a team called product management until that point in time. I spoke to the product management folks. The more I talked to them, the more I felt interested in this whole notion of an organization or this specialized group, which was helping define products and laying out the roadmaps.

It was that particular attraction that gave a sense of excitement in me to go on and venture out and try product management. That’s how I moved from being a hardcore engineer into product management. Since we already talked about my wife, at that point in time, my wife was not too sure if it was a step forward or backward. She is a hardcore engineer. We still have the debate and she normally always wins. As the saying goes, “Happy wife, happy life.”

The whole notion of product management for me has been an exciting journey from that point on. It then set me on a path where I felt just understanding the hardware side was not important and that I also needed to understand the software side. I started making shifts in my career all through to move into the software side and then started off on the silver side.

I moved to the software side of the house with systems management. I moved into networking. That’s where you and I met, if you recall, in Juniper Networks and then moved into storage. My whole journey has been about trying to learn and move to the adjacencies to help me understand and also give me that excitement of getting up every day and doing something which I completely have not had my fingers in before but gives me a chance to learn and grow.

When I look at your LinkedIn profile and background, you’re talking about big brands like Sun Microsystems, Silicon Graphics, Overland Storage, Juniper Networks, Oracle, Dell, and Western Digital. They’re all big brands and big names for sure. There’s always a playbook that has to be in play, which is, when folks are making their career transition, there is the technology side of things. You moved from hardware to expand your scope and moved on to the system side and the software side.

That’s more on the technology or technical side of things, but there are also the other aspects that are critical to one’s career growth, which are self-awareness, knowing the strengths and weaknesses, and bent to rely on others. There’s also the other element of looking up to mentors and the right folks who will “pull you at the right time.” These are all critical elements as well. Share with our readers the playbook along those lines as well.

For me, the inquisitiveness that one has to have has to be in the head. You got to go out and be inquisitive to learn and grow. That is something that each of us has to own, but then beyond that, it’s interesting you talk about mentors. It’s absolutely true. I have had some fantastic mentors in my life that I’ve always depended on to help me bounce ideas and give me thoughts and suggestions on what else I could do.

In fact, I’m scheduled to meet one of my mentors for many years, somebody by the name of John Shoemaker, who is the Chairman of Extreme Networks and who was a fantastic leader back in my days at Sun. He is somebody I still count on as a fantastic mentor who helps me bounce ideas and gives me the wisdom of all of his learnings too. As the saying goes, if somebody else has learned and they can help propel your learning that much faster and further, why not leverage it? There’s no reason to reinvent the wheel.

The best part of talking to the mentors is also that when they share some of the lessons they’ve learned and the mistakes they’ve made, I don’t have to make the same set of mistakes. I’m bound to make new ones and I’m okay with that. We have to be aware that we’ll always make mistakes. You will inherently have to go back and probably will fall, but you’ll have to learn to get up and move on. That’s the power of the mentors.

There’s something else that is not typically well-articulated and talked about, but I also think it’s important to have sponsors in your life. Sponsors are people who will be ready to also pitch for you when you’re not allowed. Something else that I’ve learned that’s crucial is to also have some sponsors in life who will be big believers in you, not just to give you advice but also to talk on your behalf and position you for maybe the right opportunity or the right role. That’s something else I would encourage everyone to think about.

B2B 27 | Customer Focus
Customer Focus: You have to be data-driven. You can’t be emotionally attached to ideas and concepts.


I’m switching gears a bit. Talking about your role, you lead product management and product marketing with a fairly large-sized business. You mentioned it’s $9 billion-plus and then you also talked about the team size, which is 100-plus people in that organization of yours. Talk to us about who you serve. When I say who you serve, I’m talking about your customers, partners, teams, peers, and executives. More importantly, how do you prioritize and ensure that all the stakeholders are aligned?

There are multiple facets to your question. Let me try and unpack it one at a time. For the fundamental question of who do I serve, the answer always has to be for each of us is customers. There’s no other way of looking at it because, ultimately, whether you are a business that’s a few million dollars in the making to multi-billion dollars in the making, you are out there to go ahead and serve your customers and help solve some of their business problems, which is where you come in with a solution.

That’s never lost on me that it is our customers that we have to serve. All through across my journey for decades, that has been a fundamental building block for everything that I’ve aspired to do is to sit down and show that we address the customer issues and problems, wherein you have with your big ears, listening to what could be the challenges that the customers are going through. With that said, once you have that covered, then you have to go rework whatever needs to be done internally to address that.

I partner with our city organization, engineering organization, sales organization, and the support organization to ensure that we have what it takes to go out and provide the necessary product resolution for our customers. They become my partners in crime per se to enable us to get to where we should be. Those are the mechanics that I go through along with the team of my colleagues, who are all propelled by the same set of ideas and cause to make sure that we meet those objectives that we are setting out to.

That’s one piece of it, but then there are the adjacencies that I don’t want to forget. This is where you have to work with other partner organizations. This is where I look at organizations that probably provide our PCBs and SoCs. There are a whole plethora of things. We depend on the ecosystem of partners and that cannot be lost out as well. If you extend on the whole distribution stuff I talked about, you have your resellers and channel partners and others.

There are partners that you bring into the fold to help you build the right product/solution and then there’s the other piece. We talked about the fourth leg of the go-to-market, which is the whole channel to go help in the distribution of the end product. That’s something else too that needs to be done and who are part and parcel of the whole planning and execution process for the whole product introduction.

I completely and holistically agree with you because I’ve been fortunate enough to speak with founders, investors, and go-to-market leaders across the spectrum. Small, large, or mid-sized businesses, it doesn’t matter, but the common thread that connects all of them is the customer outcome focus, first and foremost.

If you talk about the early days of a company, if you speak with the founder, it’s the primary research, the customer discovery and the lean startup model, which is all about going and studying the problems and then coming back and testing out the different hypotheses around the solution, how you position and package the pricing, and then your go-to-market aspects as well.

The same applies even to a more mature and larger organization. It doesn’t matter if you’re a $50,000, $100,000, $100 million, $1 billion, or even $10 billion or $50 billion. It’s the same principle and mantra, which is customer outcome focus. That’s great to know. It’s good reinforcement. For all the readers, if you’re not spending your time on customer outcome focus, please do that. That’s the primary focus.

I get that part. You’re leading an organization. You’re clearly out there studying the market, but how do you reinforce to your team across product management and product marketing that whole customer outcome focus? Do you encourage or do you have any programs around, “Go out there. Do your primary research and secondary research?” How do you build those muscles in your organization?

Whoever said life is only about ups, they have plenty of downs to deal with. Click To Tweet

Across my times in various organizations, one of the things that’s something that I’ve learned quite a bit is I use the word big ears to keep listening. You listen to what is being said and then you bring that back into what it means. There’s a distinction between what is being said and what it means because they’re not probably all the same at the same time, not because of anything else but each of the customers, if you think about it, are looking through a different lens.

For example, if you talk to a financial organization, they’re looking at how do they make the financial transactions safe and secure. They’re not thinking about the various elements in the backend technology as to how that happens. That’s our job. They might be focused on one element and be speaking to something, but then it’s our job to build a bridge between how they’re trying to look at the issue and the challenge and bring it back home as to how we can build the resolution of the right product to help enable that.

With that, it’s important that we get those inputs from various forums. The reason I say that is you probably are well-off by sending a survey. It has a set of questions with choices to make or you get a very high-level of rudimentary view, but that is not sufficient, but it gets you started. We also do what we call blind studies wherein they don’t know who is asking for this study because, at times, who is asking for that study can also skew the responses.

We have done the practice of doing blind studies, so they don’t know which organization is asking for this and then they’re more apt at giving you some candid feedback. As much as we all ask for feedback, usually, human beings don’t like to give you negative feedback, but if it is masked with some level of not knowing who that is, they’re more open to giving feedback. That’s the nature of the beast and how we work through it. Those blind studies are something else we have used to go get some more double-click, getting people in the room and having them talk through it. You get a little more depth in that.

The other thing we have done very successfully is we spend hours and days with some of the customers to ensure that we can unpack a lot of things that can’t be done by a round table conversation or survey. My point being is that you have to use multiple tools in your tool bag to go ahead, try, and make sure that you truly understand what it is that you have to solve for. This becomes more important when the time-to-market is becoming crucial and needs are shrinking.

When I started, there would be a time when you need to get a new product or a feature, it could take you two years, but now, some of the product’s spins that we got to do is probably coming down into multiple quarters. When there’s time-to-market pressure, our TCO pressure is coming in because the customers do care about the total cost of ownership.

Let’s say, if I take a server, it’s just not about, “What kind of processing capability it has?” There are other things too that goes behind it, “What is the power consumption? Does it need more cooling? Are we able to do a better analysis from a remote location without having somebody go in there in case there are any issues?”

That’s how companies are beginning to have more finite and granular TCO measurement tools, which have evolved over the period of time. You got to think through all those different elements to make sure that we are not just asking the customers, but we are able to unpack what it is they’re saying and bring it back to our roadmap design.

You mentioned quite a few things over there. It comes down to using the different tools and mechanisms for understanding your customers for customer outcomes. That’s a key message. Let’s shift gears a bit. I do want to come back into how you’re looking into 2021 and 2022 goals, but before that, as you and I know, there’s no need to reinvent the wheel. Others can learn from someone else when they make mistakes, our success story. In that spirit, can you share a go-to-market success story either from your days at Western Digital or from a previous one?

In terms of a good success story, I would take the example of at least my time at Dell. One of the things I still recall at that point in time when I joined the company, the company was shipping servers for over two decades, but we were never number one. We had the task and we took the goal upon to go out and see how we could change that to become the number one server provider in the industry.

As a team, we bonded together. I was very proud of my team for how we came down to relooking at the roadmap, looking at where the market was headed, and listening to what the customers needed, whether it was about systems management or was it important for GPUs as the advent of AI machine learning became important?

B2B 27 | Customer Focus
Customer Focus: Make sure that you have an ear on the ground, always looking to and getting the polls from the market so that we can go ahead and do what is right for not just the customers but ourselves too.


The questions of whether it is 1 or 2 GPUs they need, working with the right partners to ensure that we have the right technology brought in, and working with the CPU vendors that were out there looking at, “Where could this market be trending? Do we expect this to move ahead and continue to grow? Were there going to be adjacent markets that were going to take growth? Was there edge computing coming into play?” Those were the kinds of things that we looked back and said, “Here is what makes sense.”

We try to lay all the data we had completely, and I deliberately use the word data because you have to be data-driven. You can’t be emotionally attached to ideas and concepts. I brought the whole concept of customer-centric innovation. We’re looking at it from the lens of the customer, making sure that we’re able to go back in and plan a portfolio, and looking at the various elements that I mentioned to have the most robust roadmap in the industry and with the highest quality. We’re working with our colleagues in engineering and making sure that we’re able to bring the right products to the partner ecosystem, as I talked about.

When that came through, it did make a difference because we weren’t listening to our customers as they said here into our ecosystem partners. It helped us go back and take the number one slot or should I say if we had the opportunity to go back, relook at this stuff, and build the right portfolio, get to number one. It does help when we as a team sit down and do what we need to do in terms of listening, collecting the data, making the right calls and the roadmap, and working with our partners because this is a team sport.

It comes back to the customer outcome focus, which you and I talked about. You built that muscle at Dell and you had big numbers. If I got the numbers right, during your time there, you were part of the success story where you grew the server and the related business from $11 billion to $19 billion. Those are big numbers. It’s a testament to building that muscle around customer outcome focus. On the flip side, can you share a go-to-market failure story? I’m sure there will be plenty. It’s about picking out the most relevant for now in our conversation.

Whoever said life is only about ups, they have plenty of downs to deal with. This is in a subtle way, but it means there are ups and downs. One of the examples I could talk about is during my days at Sun Microsystems. If you recall, this is a company that gave the world Java. It gave the world some of the best possible workstations based on Unix. It was a company that could never do wrong.

I’m very proud of my association with Sun, though talking about some of the lessons learned and things that we could have done better, there are a few things. Number one, this was when Linux was still in its infancy. We had an operating system called Solaris, which our customers loved, especially the financial industry and the telco space. When you think about it in this particular market, it was all about having the most trustworthy hardware that was based on SPARC, that was our processor, and the operating system in the form of Solaris.

What we did not do was to not lead the trends moving towards open source. We could have easily gone ahead of them and looked at an OpenSolaris model where Linux would have then taken off, or on the flip side, installed SPARC used, let’s say an x86 platform, or we could have done OpenSolaris. My point being is that we continued to believe in a proprietary stack rather than moving towards an OpenStack.

Why this is relevant even now is, if we look at the industry, look at the number of things that depend on an OpenStack portfolio. We were at the forefront. We should have and could have, but we did not. That’s at least one man’s opinion as to how I think we should have learned. Likewise, where we have Java, I don’t necessarily think we monetized this as much as we should.

There’s progress in going to open source, but then the monetization.

It’s a nice way of looking at the entire portfolio but also looking at the trends. Make sure that you have an ear on the ground, always looking to and getting the polls from the market so that we can go ahead and do what is right for not just the customers but for ourselves too. That’s probably some good lessons learned.

Coming back to the question where I put up, which is, how are you looking at your 2021? Now that we are in Q4 of 2021, let’s talk about the 2022 goals. Not to share any confidential information, but broadly, how are you looking at 2022 goals for you and your team in Western Digital? More importantly, how are you thinking about the execution pieces if you can share that?

Customer focus is making sure that we learn from what's going on in the industry. Click To Tweet

There are a couple of things when I look at where we’re headed. Customer focus is making sure that we learn from what’s going on in the industry. It’s not lost on us that the amount of data being stored continues to grow. It is said that each one of us is probably storing 2 to 2.5 times more data this year than last year and you’re going to do it next year. My point is, that’s happening in our personal lives, which is why you probably have smartphones now with more memory than you ever had in the past because it’s pictures, videos, and whatnot.

If you look at the fact that most organizations now want to do more analytics on how the customers are buying or interacting with them, that means they need more data to be collected and analyzed. People talk about AI machine learning. Machine learning or deep learning, what is it based on? It’s based on data. Deep learning means you’re going to go back and analyze a lot more data than what you would do as it gives you money.

My point is, if you look at any of these trends, IoT or edge computing where there’s more data, it’s said that 75% of the data approximately is going to be generated outside of the data center, which means that there’s more data being created. For us, it means we got to provide our customers with more ways and better technologies to store the data. The way I look at this in every way I see it, data is going to be created more in the next few years than the last couple of decades.

What that means is we, as Western Digital, have to provide the right mechanisms to store the data, which is where we have a unique proposition unlike anybody else in the industry where we have the best of both flash and hard drives, which gives us the unique opportunity to be the first choice for any of our customers looking at storing data for their own business purposes.

Having said that, we at Western Digital are focused on making sure that we provide the right set of choices for our customers. Look at the hard drives. We’ve got everything from 1-terabyte hard drives all the way to 20-terabyte drives. We’ll continue to grow it because, when more data is needed, you got to go provide better technologies that our customers can depend on and we’re going to focus.

It’s interesting you asked because we introduced something called OptiNAND. OptiNAND Technology focuses on three things. It’s helping grow the capacity, performance, and reliability of our drives. We do that by vertically integrating both our flash technology with our hard drives. That’s the best part of what we’re trying to do and we’ve got to continue to do that. You’ll see all are coming to traction of some of the cool products we’re going to introduce.

It’s an exciting time, especially if you’re in the world of compute, storage, or networking. For consumers and a lot of folks outside, they may not see it, but everything that’s driving and facilitating these experiences that they use both at the business side as well as on the personal side, we’re taking a photo and storing it, making those conversations, or using your favorite communication tool. It comes down to these three, compute, storage, and networking. You said it right. Storage is critical. You can have the compute and networking, but at the end of the day, it’s still storage. You got to start somewhere. I’m excited by what’s in store with the big picture and the vision. If you narrow down your focus to 2022, what do you see are the barriers for executing against that big picture vision?

Honestly, we are dealing with some of the component shortages. It’s not just in our industry. It’s across various industries. I’ve read an article about $230 billion worth of cars that have been affected the shipping issues that we have. They said they’re going to have the Los Angeles Port open 24/7. It’s those kinds of things that we didn’t foresee in the past that we have got to work through in ensuring that we have the right components and making sure that we’re able to move parts from Point A to Point B. Those are the things that are ways and challenges that we have to overcome.

As I said, it’s not unique to our own industry, but this is something that we across on a global scale see this for all kinds of organizations. That’s the thing that I pay attention to. There are some talented members that are working through these, making sure that we come up with unique and alternative ways of dealing with that. That’s something that I would be amiss if I didn’t say it’s something that we’re going to keep a close eye on because if I look at the opportunity to where the market is headed in terms of storage, it’s a huge opportunity. The regulatory needs in each of the countries that are asking for more data to be stored and stuff essentially drive more need for storage.

I was looking back and I still recall when I was starting off. I remember looking at a 75-megabyte hard drive and you got platters. It seems to be sitting in a washing machine with huge platters and you would plop them out. Now, on a 1-inch drive, you have the ability to store 10 to 20 terabytes. That’s fascinating by itself. The innovation and market need are there, but now, some of these other elements that I don’t think most industries saw earlier are upon us.

You could come up with the best messaging possible, but if you don't know where the market is headed, you may not come up with the right messaging for that particular situation. Click To Tweet

I was talking to somebody who has been in the whole supply chain management for the last few decades. The person was talking about the fact that they had never seen this kind of supply chain challenge in their entire career. That’s something that we would obviously get out of it, but there are going to be a lot of learnings for everyone.

Supply chain issues are hitting different and various industries across the board. Especially in the hardware industry and hardware manufacturing setup where you’re relying on supply chains on the chips, memory modules, and different pieces being produced outside of the US, those have to come in. Those are big challenges that are going to take maybe a year or two for things to settle down or come back to “normal.” Those are things that are technically speaking outside your control, but talking about things that are more in your control. Looking at 2022, if you were to invest a 5, 6, or 7-figure budget or team, where would you put that focus or energy to?

The most important place is always making sure that we know where the market is headed. The focus will always be to understand the market. In anything else you do, you could come up with the best messaging possible, but if you don’t know where the market is headed, you may not come up with the right messaging for that particular situation. That’s what I would do.

My focus is making sure that we focus on where the market is headed. In this case, if I think about it, as we talk about data, more people store data. People are also looking at archiving the data. How do we come up with the right archiving methodologies so that it’s not just cost-efficient for our customers but also faster to retrieve? That is an exciting place and we call it cold storage, for example. Those are some of the things that are going to become very crucial for us.

To reiterate, are you saying that you’re going to put more time, money, or people into those areas, specifically the customer advisory board, which I’m sure you must be doing already? In addition to that, it’s about going back to the primary research and secondary research tools. That’s how you stay close to the different market trends.

It’s about, “How do you store more data? How do you make sure it’s secure and reliable?” You get it at a faster pace because you would have the data, but if you don’t get it back in a timely fashion, it’s no value. We want to be sure that we’ll be able to go build the right tools and technologies and we’ll be able to retrieve the data quickly too. Those are the kinds of things we want to answer and that’s where we’re going to focus on. That’s where the excitement is and that’s where we at WD are excited.

If you were to turn back the clock and go back to day one of your go-to-market journey, going back to your computer days, but then you transitioned from being an engineer into product management, what advice would you give to your younger self?

You don’t know a lot. I honestly don’t think I knew as much as I thought I knew. My point is it becomes fascinating and interesting when you look back and think that you knew exactly what the product is and what feature functionality should be brought out. I was pretty naive thinking that I had the answers. As you grow and mature, you realize there are so many facets to how you build a successful product and how you sustain it because the question is, it can be a flash in the pan.

You’ve got to sustain it for a period of time. There are lessons that I’ve learned and I continue to be a student for life. I’m sure there will be a lot of lessons to be learned. Don’t ever underestimate the needs of the market and think and become comfortable believing that you know everything there is to it because you simply won’t.

That’s what I call and refer to as being intellectually honest. That’s the first step and then you complement that and add on the curiosity element to it.

This is where I would say continue to stay humble.

On that note, thank you so much, Ravi. It has been a fun, great, and insightful conversation. Good luck to you and your team. We’ll cheer you from the sidelines.

Thank you, Vijay. I much appreciate it.


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About Ravi Pendekanti

Ravi is a seasoned executive in product management/marketing, developing a roadmap and driving GTM and sales enablement with a solutions view focused on customer outcomes while managing key partner relationships. Responsible to address a range of workloads including AI/ML, OLTP, HPC, Edge, IoT, Big Data and Analytics.

Areas of expertise include Servers, Storage, HCI, Networking, Systems Management, Virtualization and Cloud.

Focus is to win “Together” by building successful teams that work as a “Team” inside and across other functions in an organization and with applicable partners in the ecosystem.


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