B2B 55 | Rocket Lane

B2B 55 | Rocket Lane


Success in the world of SaaS requires relentless customer focus, strategic community building, and the courage to pivot when you face go-to-market challenges. In this episode, we sit down with Srikrishnan Ganesan, the founder and CEO of Rocket Lane, to discuss the work behind building a successful go-to-market strategy. Srikrishnan shares his journey from launch to scale, revealing how Rocket Lane became a rising star in the SaaS industry. He shares the power of staying close to your customers, using their feedback to shape product development, and building a brand that resonates across LinkedIn and beyond. Srikrishnan also explains the importance of recognizing and rectifying go-to-market failures. He shares how learning when and how to pivot and adapt has shaped Rocket Lane’s growth. Moreover, Srikrishnan reveals his unique approach to identifying your target audience and creating tailored content, emphasizing the impact of rapid iteration and experimentation in the early stages of growth.  Hear the founder’s journey and learn the art of scaling success.

Listen to the podcast here


Customer-Centric SaaS: The Rocket Lane Approach In The Go-To-Market With Srikrishnan Ganesan

I have the great pleasure of hosting another successful founder in a B2B tech startup world. His name is Srikrishnan Ganesan. He is the Founder and CEO of Rocketlane. I’m excited to have you on the show.

Thanks for having me on.

This has been a trend in our show off late, which is you are one of the references from a previous guest who came on the show. I’m grateful and happy about the fact that guests are referring other guests. It also goes to show how well-connected you are within the startup community.

We have a nice community that’s been growing, helping each other out, and learning from each other. I am glad to be part of it and excited to see all the progress many companies are making like a cohort of companies that start around the same time. Everyone is growing, learning, and evolving.

Let’s get right into the meat of the topic, which is how do you view and define go-to-market?

The way I view and define go-to-market is there is a series of motions that need to be in place. Part of it would fall under the marketing side and sales side of things typically, but it’s about how you are creating a presence for yourself in the market and getting your product into the hands of customers. Part of it is audience building, getting people to come in and check out your offering, and outreach you’re doing, like the outbound motions that you may have. How are you even messaging this? How are you crafting the right story for what you’re selling? This can be taken by many marketing channels, and one is to one channel to the right audience to pull them in and convince them to buy. That whole journey is what I view as go-to-market.

You touched upon quite a few things that I want to echo and highlight. You talked about the connection between product marketing and sales. That’s one piece. Second, you talked about audience building and community building. We’ll dive into that pre-flight community that you have been building. That’s a second aspect.

Third is the storytelling aspect. All of these pieces have to come together to connect the dots between what is a pain point? Who is a pain point? Who are you addressing it for? How is your product solving it? Let’s step back, take a bigger picture of your career, and walk us through your career journey and what led you to what you’re doing NOW.

Deep in my heart, I’m a coder. That’s what I enjoyed doing through my undergrad years. I surprised myself and others around me. I went to B-School immediately after my undergrad, but I was still in love with technology and creation. I was like, “I want to be a product manager.” I found a career in product management at Verizon and an Indian company called Rediff.com. Think of it as the Yahoo/AOL from India, an early web property. It’s stuck in between being a media company, a product company, and a tech company in a way.

I joined a startup as the Head of Product in a company called Jigsee, which was acquired by another startup a few years later. That journey gave me a lot of confidence in building not a product but a company because I was one of the first three employees. Three of us joined on the same day. I built the team and company and looked for office space. You need to have a certain false sense of how easy it is. You need to be a little delusional to start. That delusion had happened at that time. I was like, “I did it at Jigsee. I can do it on my own. Let me go and do a startup.”

B2B 55 | Rocket Lane
Rocket Lane: You need to be a little delusional to start up.


I pulled in a couple of friends. Three of us were excited to start on a journey. We started with something B2C and pivoted into B2B in the messaging space. We were trying to take on WhatsApp and pivoted to do B2B messaging SDK. That startup was acquired by a company called Freshworks in 2015. The three of us continued to build that business within Freshworks for the next several years. That was going to a SaaS school in a way for us. We learned a lot in that journey. We decided it was time to graduate and try something on our own again. In 2020, we started Rocketlane. That’s been my career.

You got into product management with Verizon and the FiOS TV. As a side note and related notes, I was at Microsoft Media Room, the IPTV platform, doing product marketing. Our worlds crossed back then. We didn’t know each other back then, but I can relate to that world of yours. You switched to Rediff. You also mentioned being an early employee at Jigsee and Konotor. That’s the startup that you co-founded, which was acquired by Freshworks. Now you’re onto your second official startup, which is Rocketlane.

It’s been a fun ride.

Given this varied path, how do your family members describe what you do?

They know I do a ton of things. I’m on customer calls quite often. They know I always, from Jigsee days to Konotor days to now, do a bunch of customer support myself. I’m jumping on not just escalations, but if I have free time and see someone chatting with us, I would try to jump on that. For them, it was like,  “He runs the company. He’s a CEO at a high level.” They know I do that. I am more on the sales side in our startup. That’s how much they know.

You seem to do and come across as everyone or every role for your family. If you are a founder, you need to wear multiple hats, and the fact that you have a supporting family gives you the space, time, and energy, which says a lot about the family support you are having. Coming back to what you were doing at Rocketlane in the early days, walk us through it. What is Rocketlane? What prompted you to go down this path? Who do you serve in this space?

This stems from personal experience. We look back towards the end of our journey in Freshworks. What was a broken experience for us or our customers in the whole seven and a half years we spent building this business? We were thinking, “Are there teams that were underserved? Are there experiences that were playing wrong?”

One thing that stuck out was the implementation journey. You’ve sold an amazing deal, and now you’re worried. We sold all of that. We’re going to transfer that context to the implementation team, but who do we put on that team? You have some heroes in mind from the team. You are like, “If I give it to Sodir, he’s going to do a great job, but he’s already doing these three other big projects. Who’s going to manage this? If I give it to someone else, will they do a sloppy job?”

It’s hero-driven as an experience. It’s the first partnership that the customer is experiencing with you. Post-purchase, the first partnership. A lot of people on the customer side are in the dark about what’s happening. A leader on the customer side only knows, “It’s been several months since I purchased this. We are not yet live.”

B2B 55 | Rocket Lane
Rocket Lane: A lot of people on the customer side are in the dark on what’s actually happening.


You may have reasons to say, “No, it was your team. Here is where the problems were. This integration didn’t work.” There are excuses but when you think about it, the ball is always in your court. That’s how you should treat it. That’s where we said, “There is scope for something different.” Instead of using a bunch of ad hoc tools like Slack, Asana, Notion, Google Docs, email, SurveyMonkey, or all of that together in this implementation journey, what if we build one all-in-one experience that is purpose-built for running customer-facing projects?

We didn’t say to just implement it. We said, “Let’s go after customer-facing projects of all kinds where there is an internal team, external team, and potentially a partner team. They’re using a bunch of silo tools. Let’s stitch together those experiences.” If you’re running a services team within a product company or a services business, you also want to learn where people are spending time. You want to tie effort to revenue from that project.

There are the PSA capabilities, time tracking, resource management, rate cards, and project accounting. We brought together all of that as one offering. We play in two key categories. PSA, Professional Services Automation, and client onboarding. That’s what the tool helps with running customer-facing projects and services projects. How do you hold each other accountable? How do you provide a better customer-centric experience? How do you automate a lot? Because it’s purpose-built for these projects, there’s a ton of automation that’s never been dabbled in before that we are able to enable.

That’s what the best founders do, which is to figure out what is the problem that they saw firsthand. They build a hypothesis around it. They go about validating the problem and building a solution for those personas. Coming from Freshwork and even at the early time in your prior startup, you had that hypothesis that onboarding and implementation were potential pain points, but that’s in your mind. How did you go about validating? You need to have that customer validation for the first 5 to 10 early adopters or beta participants. How did you go about doing that?

We didn’t write a single line of code, launch an MVP, or do any of that early on. We said, “Let’s focus on validation. Let’s talk to as many people as we can.” We took two and a half to three months. We spoke to around 60 to 70 companies. We spoke to different roles in these companies. We spoke to the CEO, CCO, implementation leader, and implementation manager. We want to get all the perspectives. Some of them are their investors.

Is this a big problem? Does this problem have visibility? Is there value assigned to or related to solving the problem? Is it one of the top five problems for the company? Is it one of the top five problems for the CCO? We want to know, at each level, where this priority for solving this problem lies. One thing we found was there are enough companies, especially within SaaS, which is what we started with as our beachhead, where people cared a lot about that time to value and launch.

The reason was time to value creates a stickiness. Time to launch is essential for pulling forward revenues. Closed ARR is far ahead of your live ARR because a lot of customers are stuck in implementation. That’s what investors and CEOs cared about. On the other hand, when we talked to the CCO and implementation head, we got a little more perspective on what are their key challenges. They want to hold customers accountable in a better way. They want more automation and streamlined experiences. They want their teams to follow the playbook the right way.

All of those problems came out. We started thinking. How can we solve all of this? What experiences will help? We use an approach called jobs to be done to build a product. Before we build a product, we want to understand the jobs to be done by the people and the software we build. We came up with the right hypothesis of what can help these people. Is it a people problem, a process problem, or a system problem? Where they see it as the problem, there should be elements in the product that can help them with the people problem, process problem, and the system itself.

B2B 55 | Rocket Lane
Rocket Lane: Before we build a product, we want to understand the jobs to be done by the people and the jobs to be done for the software we build so that we come up with the right hypothesis of what can actually help these people.


That’s the journey we took in early validation. We spent enough energy on it. We talked beyond what we felt was our ICP because early on, we said series B plus companies is what we want to focus on. Opportunistically, we’ve met an early-stage founder. We’ll also talk to them and understand how they think about this.

It helped because we uncovered that an early-stage company, a seed series A and early series B type company, somehow made things work on time. That’s the only thing they focus on. They have only a few customers. They make things work but then they want to come across as professional. That was their problem. They wanted to look bigger than they were and make an impression. “We said, “That’s also a problem we should try to solve.”

The last point you mentioned boils down to the messaging. Messaging to a persona or ICP that is pre-series B versus messaging to a post-series B would be different. That’s the early validation phase. You said that you spoke to 60 to 70 people in a 2 to 3-month timeframe. At the end of the three months, is that when you had a good idea of the product hypothesis and business model?

We started working on high-fidelity prototypes of what we felt were key experiences that the product needs to enable and key problems that need to be solved. Beyond that first three-month period, we started to build the basic building blocks of the offering. We also started to show people these early prototypes and marked click-through prototypes to say, “We don’t have a product yet. We are not selling to you. You described the problem before. We want to show you how we are thinking about the solution. Let us know if this resonates with you. Let us know if you think this will solve the problem or if there’s something else that could be magical in this experience.”

We started doing that over the next year. We didn’t launch an MVP. We launched a full-featured product. Along the way, we kept showing the product and the prototypes to more people. I had a notion document with 120 companies, the contact, what feedback we were hearing from them, and what stage they were in from the conversations I had in that period where only the conversations that I felt were worth pursuing. I added it to this list. Having a CRM. We had a notion table with all of this data. When we launched, we went out to all of these folks.

This was in April of 2020 when you officially came out, and you incorporated Rocketlane.

That’s when we incorporated. We came out in June 2021.

Something else that caught my attention, and kudos to you and the founding team, is you built a community from the early days, the pre-flight community starting in September of 2020.

That was nine months before we launched our product, which is unique. Most people think about it after some traction.

Many people don’t even think about it.

Two things happened here. One is as we had these conversations with people, I wasn’t focused on what the software does. I was trying to understand the people problems, the process problems, and the system problems. I could see that different kinds of companies were focused on solving different pieces of the problem.

Some of them that were more enterprise were more focused. They were like, “I’m holding customers accountable. I need a steering committee so that the key decisions are made on time.” There were some folks that talked more about how you start the journey matters so much. Start with the right intensity. What do you do at kickoff matters? In every conversation I had, I would ask them about where things were several months ago. How have you evolved? What are you focusing on improving?

There was so much learning for me personally on what people were trying out to solve problems and implementations launch faster, giving a better experience for the customer. If everyone is focused on different things, its implementation feels like one part of the customer journey, but it’s a complex part. If I get these people to talk to each other, there’s so much cross-pollination of ideas that can happen. All of them can benefit.

B2B 55 | Rocket Lane
Rocket Lane: Implementation feels like one part of the customer journey, but it’s actually a very complex part.


I invited one of my friends who said, “I used to have a six-month-long implementation. I’ve shortened it to six weeks.” I was like, “Tell me more. I’m open to talking about this to a wider group of founders and practitioners.” He said, “Yes. Organized a session.” We called it an implementation story session where he talked about all of it. There were many questions and engagement.

Was it a Zoom virtual or in-person session?

It was Zoom. This was during the pandemic. The session was very engaging. There were 25 people who joined. There are many questions. I was like, “He’s got to go. We can continue the conversation on Slack. Let me create a Slack group.” That’s what turned into pre-flight the community because I already wanted to do the community.

This became the catalyst for that action to happen. We said, “Every month, we are going to invite two people to talk about how they have evolved their implementations, and let’s all learn together.” It was a great source of content and building an audience because we started reaching out to folks about these events. We said, “Join the community to get access to the events.”

Did you invite that speaker? Did you have that first session after your 60 to 70 conversations or even before?

It was after the first 60 to 70 conversations.

We can deep dive into this topic alone, but we’ll save that for another time. You are several years old now. You are yet in terms of number of customers, revenue, and funding.

We keep the revenue part private. We have over 400 amazing logos that have come on board. It’s companies like Clari, Drift, Mixmax, Vidyard, Unifor, Amelia, and a whole bunch of amazing logos globally. We raised $21 million of funding to date. That’s an $18 million series A and a $3 million seed that we did. Things are on a great track from the momentum perspective, given it’s a few years from launch.

Thank you for sharing your growth story and journey. That’s commendable. I’m excited and happy for you guys and the way you’ve been validating the problem and building your company, Rocketlane. I’m switching gears a bit here. Let’s talk about a go-to-market success story and a go-to-market failure story. It can be for you when you are building Rocketlane or any of your customers.

I would say go-to-market success story. I’m going to use the example of what we did on G2. Early in the journey, we said, “We need to get a good presence on G2.” We saw that we had few competitors at the early stage in this category called client onboarding. The highest one had 80 reviews, and it felt beatable. We had 30 customers in the first two months since launch. It shouldn’t be hard if people like the product to get them to review it. That’s something we focused on.

It wasn’t like marketing owns it. It was like all of us owned it between customer success, which drove a lot of sales, marketing, and anyone in the company. If we knew there was a customer who had had a good experience with us, we would pounce on them for a G2 review. We push them to rate us and give that ranking. We are number one on G2 in our category. We are the highest rated and highest number of ratings in the category.

I’m proud of what we accomplished over there. It has a big impact because, in the early days, we focused a lot more on SMB. Now we have a lot of mid-market and above-type customers, but all these folks search for tools and alternative tools. If you come up in the top 2 or top 3 on a platform like G2, you make it into the consideration set. The number one always has a lot more momentum in the sense that people consider that first. They talk to them first, and they ask the others, “How do you differentiate from the number one?”

In that sense, it puts you in a poll position in any competitive evaluation. That’s what you want. That would be a success story. There are a lot of tactics and specific things we did to get that momentum on G2. We are happy to chat one-on-one with people on that, but it was a great investment of our time and energy for that phase of our journey to get up to being number one in that space.

If you can share 1 or 2 tactics, what drove the success that would be helpful for the readers?

If someone has a support issue they came up with, and you delivered a good experience for them, and they say thank you, that’s a moment for you to latch on and say, “We are always happy to help you. We’d also be glad if you’re able to help us and leave a review for us on G2. It means a lot for us as a growing business.” Add that emotional appeal, ask them, and they will do it.

The other thing we did is if you give something, you get something. Sometimes, customers ask for discounts, especially early in the journey. We said, “If you want a discount, we give you this discount, but in return, we need G2 reviews from your team.” We can’t control what they say in the reviews, but we push people to give us those reviews. There are ways to incentivize.

We can't control what customers say in the review, but we can push them to give us those reviews. Click To Tweet

When I was running go-to-market and marketing teams and even product growth in previous companies, that was one of the tactics that we used to do, which is to run an email campaign and a phone LinkedIn campaign and even offer gift cards. Gift cards are more to get attention. I’ve seen the quality of reviews not necessarily tied to the value of the gift card. It’s more of how happy that customer is with that product or service. Gift card is a little cherry on the topic. Now go-to-market failure story because we all know it’s not success all the way. How about a go-to-market failure story?

There’s a big lesson from my previous journey. I don’t know if your show reaches more early stage and late stage. There’s a big lesson for anyone in the early stage, at least from my previous journey. We launched this SDK that went into other people’s apps and enabled rich conversations between customers using apps and businesses.

Is this from your time at Konotor?

This was Konotor. Even inside Freshworks, we first relaunched as Hotline.io. We had the same problem go-to-market problem over there. This was an evangelical product in the sense that people weren’t looking for it yet. They didn’t know that they could deliver a WhatsApp or iMessage-style experience inside their app and why they should do it. We had to educate the market a fair bit.

We were ahead of the game in the journey already because we had to go, educate the market, and tell them about how this would create a better experience for customers and how that would lead to stickiness for their apps. Most apps, back in 2012 and 2013, were still figuring out what their app should do. They weren’t in a frame of mind to say, “I need to improve the support experience inside my app. Who should my app serve, firstly?”

When we showcase this, there are companies of all kinds. There was enough feedback we got saying, “Can you also provide this for the web? We want to use one platform for web and mobile.” We did not listen to the customer and not even to our own sales manager. We said, “The experience for web live chat is different from WhatsApp-style asynchronous communication. That’s what we are focused on. We don’t want to dilute it by trying to serve someone else.”

The reality was no one in this mobile messaging space, and the mobile SDK space grew fast. Everyone was slow and chunky growth. On the other hand, there were companies like Intercom and Drift doing what we did for web apps. They were growing like crazy. We completely missed the bus on that. We could have been there. We could have been growing that fast as a bootstrapped startup, and we missed that completely. The size of the market and a real validation of who will buy, why they will buy, and what the priority is. We missed all of that in our thinking about going to market. That is one weakness.

The reality was no one in this mobile messaging space mobile SDK space grew fast. Click To Tweet

How are you fixing that at Rockelane, where you’re not missing out on those big signals that are coming out?

If we didn’t have the momentum we had in the first two months, we would have pivoted immediately. Optimizing for momentum is the learning over there for us. What that also means is you can’t do anything in a half-hatted way where you’re thinking, “Was it A or B? Was it because I didn’t do enough marketing? Was it because I didn’t have a good brand? Was it because I didn’t have the right message?”
You should test out everything quickly. You shouldn’t be like, “I’ll spend six more months and then I figured out maybe it’s the message or I need to change that.” There needs to be rapid attrition and a lot of early validation of the messages before we even launch the product.

You should test out everything quickly. Click To Tweet

That’s been how we’ve approached things at Rocketlane. When you’re doing something, do it in a way in which there’s no second guessing on why it did not work and extending the timeline of an experiment to say, “It didn’t work. Let me try something else for a longer period of time.” We started doing Google Ads early because we wanted to understand, “Will this be a channel that will scale for us? I didn’t want to wait it out until a certain point in time and a certain number of customers before spending on ads. Let’s do it.”

What also surfaces in my mind when you’re sharing this story is the role of product marketing. Early on, especially in the early days with the founders who are wearing the head of product marketing, and as you scale, it looks like you’re at 80, 85, or 90 employees at Rocketlane. As a founder and CEO, what is your message to your product marketing team? What are the challenges that they’re dealing with?

The big thing that we focus on is people are actively listening to customer conversations every day, whether you’re in marketing, product marketing, or other functions. Even our engineers listen to customer conversations because you build context on what the pain is for the customer, what words resonate with them, and how they describe their problems when you listen to it from the horse’s mouth.

Listen to customer conversations because you build so much context on what is the pain for the customer and what words resonate with them. Click To Tweet

There is nothing better than building context together. From day one, we’ve recorded every single conversation we had, even those first 60 to 70 conversations, before we decided what to do. Every prospect conversation is recorded. We use Avoma. We auto-generate these summaries that get posted on Slack. People read that. That’s a trigger for them to go and watch a conversation.

The biggest thing is how we build a common context. I don’t even have to say anything. People know what’s happening. What does the customer care about? From a direction perspective, we want to set direction by saying, “We want to focus on that mid-market customer. Watch out for more of these calls. We are trying to sell to services companies, not services teams and SaaS companies, or the message needs to change for that audience. Who do you want to talk to? Let me facilitate.”

We had fifteen service leaders do sessions for us. They did it pro bono out of the goodwill of their heart. There’s a promising company that’s taking a certain direction. Let’s spend time with that team. Let’s tell them about our world. If people get curious, they will ask questions. Validate like, “What’s the top priority? How would you describe this problem? What do you think will solve this problem?”

The way I look at product marketing is you can break it down into 6 to 8 categories or programs. You have the positioning, messaging, customer insights, competitor insights, sales enablement, new product launch, new market launch, product content, and product adoption. You have ticked the boxes, especially in the early days, where you have focused on the customer insights program and making sure that every employee, not just marketing or sales, is listening to these customer conversations.

Going forward, something that caught my attention is you mentioned going upmarket. It looks like if you were to pick an area that you want your product marketing leader or marketing leader to focus on for your go-to-market, which would that be? Would it be like a new market, product content, or product adoption?

It is honing in on this new market we’ve landed on and ensuring that we are enabling the sales team to approach that market the right way. We’re doing a lot of enablement sessions internally. We focused on that.

Given that you’ve got a good track record when it comes to early company building and fundraising, what are the 1 or 2 things, especially when it comes to go-to-market, that industry peers or folks from your network reach out to you for? They go, “This is something that Sri is good at. Let’s go reach out to Sri.”

There are a few things I would say. One is marketing. People keep reaching out because we have quite a buzzing social presence like LinkedIn presence. People reach out about that. It’s more brand than demand gen or other stuff. Community and brand are areas where I think people keep reaching out and sales momentum. Early-stage founders reach out about the 0 to 1 journey, which we did within our first year of launch. That was a fun early first year for us. A lot of people have heard about that. They reach out to ask about what are things that you did, mistakes, and learnings from that early journey.

You have all the items in a successful or winning go-to-market. It was around content.

Another area where people reach out is if they have problems with their implementation or onboarding.

It goes without saying I was diving deeper into what other, besides your core offering and core expertise. The point I mentioned earlier is you have all the key ingredients and elements when it comes to winning go-to-market, which is the content. You have community and experience/events. It goes back to doing that early reach out, validating the problem, and building content around it, which is your presence on LinkedIn and others. You have the community, which is a pre-flight community, and experiences and events. You must be running some customer events and having a good presence in industry trade shows.

That’s an area we pride ourselves on in terms of in-event execution. In pre-event planning, we could do better. At the event, we are the hungriest team, and we do some unique things over there.

We’ll save that for another episode. I have the last couple of questions. I know you need to head back to your company building days. The two questions I have for you are, who are the 1, 2, or 3 people who have played and shaped your career growth, and who have played a key role in your career growth and inflection?

One is Girish Mathrubootham, the Founder of Freshworks. I got to work closely with him. I’m a huge admirer. I learn every time I meet him. I learned something from him. I would say Krish of Chargebee. He is another founder that I have. I get different perspectives from Girish and Krish on a lot of things. I need to figure out what I want to do. It’s good to pick their brains and get that different perspective. There are many founders, like Ashwini from Mad Street Den and Sahil from Rattle. There are a lot of folks who are on similar journeys with us. I’m big on community. The same applies to the founder community. I’m actively learning from a lot of people.

That’s a key ingredient. It doesn’t matter which part of your go-to-market journey you are in, early days, or even the growth and scale phase. It’s important to have a personal board of advisors. You’re building that. Do you carve out an hour a week? Is it one hour a month? What is your focus in this area?

It’s sometimes more reactive, but I have cadences with 3 or 4 founders. We have it on the calendar for one hour a month to go over a bunch of things together.

The final question for you is, if you were to turn back the clock, what advice would you give to your younger self on day one of your go-to-market journey?

Hire leaders faster.

Why is that? Why did you come to that realization, and when?

We hired a sales leader who’s been impactful. It’s given me more time and energy to focus on other things. It tells me, “If we make the right hires earlier in the journey, it makes it easier for everyone, including the teams you’re building.” You can do more justice to your team if you get them to work with a great leader.

If we make the right hires earlier in the journey, it makes it easier for everyone, including the teams you're building. Click To Tweet

Thank you so much for your time, Sri. I enjoyed the conversation and the actionable insights that you shared with the readers. Good luck to you and your team at Rocketlane.

Thanks so much, Vijay.


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B2B 52 | Clin.AI

B2B 52 | Clin.AI


Start before you’re ready. Entrepreneurship is about embracing uncertainty, trying new things, and learning from every step along the way. In this episode, our guest, Kalyan Obalampalli, discusses the journey of his creation: Clin.AI, a groundbreaking platform for clinical trial vendor selection and management. He reveals the ups and downs, the moments of doubt, and the incredible perseverance it took to build a product from scratch. Kalyan shares how he transitioned from a free pilot to a paid subscription model, scaling Clin.AI to possibly six-figure annual contract values. But entrepreneurship is not all smooth sailing. Kalyan shares his honest go-to-market failure story, where he experimented with marketing agencies and discovered the importance of a founder finding their own voice in messaging. Throughout the episode, Kalyan’s key advice to his younger self resonates: “You don’t know where you can go unless you start.” Tune in now to gain a fresh perspective on entrepreneurship and innovation!

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Clin.AI: Pioneering Automation In Clinical Trials With Kalyan Obalampalli

I have the pleasure of hosting a Founder, CEO, and a good friend, Kalyan Obalampalli, who is the Founder and CEO of Clin.AI. With that, welcome to the show, Kalyan.

Thank you, Vijay. It’s a pleasure to talk to you. I’m looking forward to this conversation.

Same here. We have been in touch over the last couple of years. I’m excited and happy for you to see how we have grown your company from an idea to what you’ve been doing so far. We will unpack all of that in the episode. Welcome once again. As with each and every guest of mine, I always start with the signature question. This show is all about go-to-market, and I would love to get your perspective. How do you view and define go-to-market?

I don’t have any formal knowledge. I didn’t ever delve into understanding what go-to-market is, to start with. I was like a startup founder who found the idea, believed in it, and didn’t figure out how to sell it. The way I have at least thought about go-to-market is, “What am I selling? Who’s my customer? How am I going to sell it?” Those were the questions that I saw in the most basic definition.

Over the years, I identified some gaps in the industry. If you remember, you were kind enough to tell me the most important thing, which was to interview a lot of people and understand, “Is this a problem or not?” Fundamentally, that’s where we started. We understood it was a problem and then believed in it. We gave the clarity after all the interviews that it was an issue because, a lot of times, the question that came to me was, “This is so simple. How can this still be a problem? How come people haven’t thought about a solution?”

Once that was said, we built a product that helps small to mid biotechs with vendor selection. The second thing was we identified who needed it the most. The bigger companies needed it, too, but we identified our ideal client profile to be small to mid biotechs with less than 200 employees in most cases, although we have clients bigger than that.

How do we reach out to them? That’s the part where I struggled quite a bit, but what I identified was our industry is pretty traditional. I identified that the way we are going to find our customers was to go out into the market, go to conferences, speak to people, and make that personal one-to-one relationship, and that’s where I can make them understand the value proposition.

Interestingly, my first client turned out to be one of the first twenty interviews that I did in 2020 after our discussion. One of them picked up the phone. She talked to me for twenty minutes. When I built something, I called her. The funny thing is what I built was not what she needed. She said, “If you build this, I’m going to use it.” As you know the story, I learned how to code. In a month, I built what she wanted. That was how we go-to-market.

The way I summarized and took away from how you view and define go-to-market is it’s very typical with founder-led startups and founder phases or approaches in the early days of a startup, which is based around the basics starting with, “What is a problem? Is anyone out there solving this problem? What is the problem that I saw firsthand? Let me go out and validate if it’s a problem.” That’s one. Second, if it’s a problem, someone is willing to pay money for it. That’s super important as well. That’s the approach you took for your go-to-market, and that’s how you view, approach, and define go-to-market.

In the process, similar to how we touched base, I touched base with the CEO of a small company who had sold his company to somebody else. He was the first one who challenged me. I was telling him about how many contracts we have facilitated through the platform. His question was, “How much did you get paid?” That’s a question that hit hard, but that night was when I wrote my first proposal asking the company to pay me for my services. A month later, they signed the contract.

Let’s zoom out. I’m sure we will unpack and get into a lot of the details around Clin.AI, the go-to-market, the clients, and so on, but let’s zoom out a bit over here. Why don’t you tell and share your career story with our audiences? Who is Kalyan? Why did you choose this space? What were you doing prior to Clin.AI? Let’s take it from there.

I’m in the pharmaceutical industry running clinical trials. That’s what I’ve done. How did I get into it? I’m an engineer by education. Due to many reasons, I fell into this space. I was in preclinical research, and then I got into clinical research. Since then, I’ve been doing this for years and running clinical trials. People are a lot more familiar with what clinical trials are after COVID. That’s what I’ve been doing so far.

Throughout the process, I’ve always wanted to do something for myself and start my own business. In 2016, I started something to do with vending machines. It had nothing to do with my education or anything else, but I wanted to do something fun. I didn’t have kids at that time, so I had a lot of time on my hands. My wife always used to encourage me to do something in my field because she thought that might be the best use of my time.

As I kept thinking about things, there were clinical research and clinical trials. If you talk to anybody, there is no dearth of gaps. There are so many things that we do on paper or Excel files. It’s almost unbelievable we’re that far behind. It’s well-known that the uptake of technology is very slow. That’s where I identified a few gaps. You have to hit upon a challenge that you’re so passionate about that you want to solve it.

In the process of running trials, everything is outsourced. You outsource things to vendors. When you outsource, the contract costs or the contract values are anywhere from $2 million, $3 million, $5 million, $10 million, $15 million, $20 million, $30 million, $40 million, to $50 million. We were negotiating these all the time using Excel files, and that’s how we did it. I felt that the amount of due diligence I was doing was less than what I would do even if I hired someone to remodel my kitchen. That’s how I felt.

In 2020 September, I selected vendors for $100 million, which eventually became $130 million because of changes and change orders. That was it. I decided somebody had to do this. I quit my job and bought a laptop. It was me and a laptop. I remember walking into this building, looking for a shared space, and learning how to code. That kept going on. I kept coding, built something, and pivoted as every other company does. That’s how Clin.AI started.

That’s a very cool story. Kudos to your wife for pushing you into doing a startup and working on a problem that’s close to your main field versus vending machines. I want to get into the vending machine story though. What prompted you to go down the vending machines? What did you learn? I’m sure if you go back and connect the dots, everything plays a role.

First of all, as far as my wife’s advice goes, I give credit to me because I listened to her. The vending machine thing has a critical role because when I started that business, it was about providing healthier products to the customers using vending machines. That’s what I was doing. The machines were state-of-the-art. You could use iPhones, Google Pay, Apple Pay, or whatever you want on these machines. Plus, you get organic and healthier products.

When I started, there were two companies that I finalized that I would probably work with. I ended up working with one of them, and it worked out. The second that I did not choose went bankrupt after nine months. The first thing that I understood was it’s very important to choose partners. It’s about people. It’s not about the amount of money you’re going to pay them. I went with the expensive one, but I knew that this company was not after my money. They were going to give me at least what they said they would provide. That was my first lesson.

It's very important to choose business partners. It's about people, not the amount of money you're going to pay them. Click To Tweet

The other important thing that came to my mind was, “How do you get customers?” You have no idea how to get customers. I remember walking into this college. I knew nobody there. I walked in and talked to this guy who was sitting in the cafeteria. He was managing the cafeteria. We started talking. Initially, I couldn’t strike a chord with a lot of people, but then this is a place where Pepsi was already there. I walked in and talked to this guy. We got Pepsi out of that college, making a case, “This is unhealthy stuff. Maybe you should offer healthier stuff.”

It was not that easy to sell, but eventually, I was able to kick Pepsi out, which is a huge deal in the vending machine area. That gave me confidence that I could possibly walk into a business that I have no idea about and talk to a customer that I have no idea who that is. People give you a chance. People don’t buy the product. They buy you. That was my first lesson in learning that.

That’s a great story and lesson there. How did you manage to get Pepsi out of that cafeteria? I would assume you or the cafeteria person would have gotten some incentives to keep Pepsi in there. How did you work around that?

Pepsi is huge. That’s a good and a bad thing for them. It’s good because they can give a big percentage of their sales to the college. It’s bad because the products are horrible. It’s full of preservatives. You know the story of the snacks that they make. For example, Pepsi snacks won’t go bad for the next year and a half. They sit in the vending machine forever. This stuff can be good for you. If you look at some of the colleges, there have been a lot of movements in the colleges like Ban the Bottle. They don’t want any water bottles and things like that. The colleges or the next generation are moving into that area.

Those were my talking points. I made a case, “Would you want to consider giving something? I’m not saying that this is perfect. This is healthy. Do you want to get to that next step where you are providing products that are healthier than what you have? You can’t go to healthy. You can’t start putting bananas in there because nobody is going to buy.”

That was our step, “Do you want to take this interim step to get slightly closer? We’re never going to have sugary products like Coke or Pepsi. This is what we’re going to have. We’re going to have organic bars and things like that.” That was attractive to them. They felt like they were going to make a move in the positive direction. It’s going to be seen as a positive step by their management. That’s how we were able to sell it. Financially, we tried to make it as attractive for them as possible. It’s a combination of the intent and the monetary side of things, plus making a case that they can sell internally. That’s how the whole vending thing started.

Those are all key points, especially in the B2B space where you have to connect with the buyer or the person who has the buying power. More often than not, especially in B2B, it’s not one buyer, but it’s a team of buyers and influencers.

There’s more than one person who makes the decision. Another big lesson that I learned was how you service the client is another important part. You can get the contract, but then if the customer is not happy, it’s very easy for yourself to get demotivated and also for the business to collapse pretty quickly. That has been the mantra for Clin.AI when I started. The biggest thing was to find customers and then make them extremely happy. That has been how the company has grown so far. We have spent probably zero on marketing in quite a few months, maybe up to a year. We spent nothing on marketing. It was all word of mouth and people talking about us. I didn’t mean to digress there, but that was something I kept to my mind.

You can get the contract. But if the customer is not happy, it's very easy for your to get demotivated and for the business to collapse. Click To Tweet

This is relevant to the next topic that we are going to talk about, which is where is Clin.AI at in terms of customers, pipeline, revenue, or whatever you’re comfortable sharing with. We all know that it’s still early days. No number is small. It’s more about the growth. It will get bigger and better from here.

2022 was a great year for us. 2021 was when we launched, but that was the year when we were testing the system. It takes about 4 months to 5 months for a vendor to be selected because these are anywhere from $15 million to $30 million and $40 million of contracts. In 2022, we had an excellent year. We have ended up with a very strong number of customers.

In terms of how we have grown, we have seen a 500% growth year over year from ’21 to ’22. ’22 to ’23 may not be in terms of customers but in terms of revenue. We’re going to be six figures in terms of signing contracts. We will have to wait and see how everything turns out. It’s not been easy, but fortunately, we have hit upon an area where there is a need because I remember going to a conference. I was late for breakfast. I was kicking myself that I spent all this money and came to the conference, and now I wake up late. I was late for breakfast. I was getting into the elevator, and somebody else was late too. We had breakfast together. They became a customer. I figured out, “I’m walking into customers.”

I felt like this is a need in the industry. That’s where we started in 2021, but now, we have seen significant growth so far in terms of how we have done it. One of our customers has been telling us we have saved them $8.5 million in 2022. The ROI in at least one of the cases is greater than 100 to 1 or something along those lines. That has been our story.

We’re making sure the customers are extremely happy, using their word of mouth, and getting more customers. In 2023, we have invested quite a bit in getting a salesforce on board and also going to a lot more conferences and having a lot more discussions. That’s where we are. Another significant step in this is we took a step back earlier in 2023 to build another product.

Generally, what I kept hearing from the people I was talking to was, “If something is selling, keep selling it.” Although I agreed with that, I felt like vendor selection was one part of it. You have to manage the vendors too. We took a step back for about three months and developed another product for management. We have rolled it out to a few customers. It might become our flagship product in the future.

Back in the days when you and I were talking, you were contemplating building a marketplace on a platform. Think of it. If you are trying to build a one-sided marketplace, let’s say the pain level is 100. If you’re talking about a two-sided marketplace, the pain level is 500. It jumps exponentially. You and I went back and forth. The advice that I gave is, “Which side is willing to pay? Start on that side of things first.”

A marketplace is a very simplistic idea that a lot of people dream about. In the limited research that I did or whatever I could do, I learned that there’s only one marketplace typically that survives the market. Facebook was the last one. Beyond that, maybe there haven’t been too many of a similar kind. It’s a simplistic idea. As we discussed, which side do we go after first? A marketplace is something that people can get to eventually. The main thing is to start on one side, find the pain point, start filling that gap, and deliver the results.

B2B 52 | Clin.AI
Clin.AI: Start on one side, find the pain point, and start filling that gap and deliver the results.


I have a lot of vendors reaching out to me, “Can I be on your platform?” There’s no need to be on our platform. If a sponsor wants to reach out to you, we will get you on for free, but a lot of people keep reaching out. That’s a good sign. Will we implement that in the future and make that a main part of our business? It’s something that we can contemplate in the future, but as of now, we have identified an area or a niche of selecting vendors and managing vendors. We want to stick to that. Eventually, will we serve both sides? We potentially may, but as of now, we’re going to park that idea on the sidelines and consider what’s working so far.

Here’s the reason why I wanted to bring it up, especially for the audiences who are aspiring founders or founders in the early stages. You can, you will, and you should go with a hypothesis. In your case, it was building a marketplace. Maybe that’s a pain point, and maybe that’s what you need to pursue, but after you reach out and talk to “the buyers and customers,” that’s where your hypothesis will evolve. It was not the marketplace.

Those interviews were critical. I give a lot of credit to the interviews for this reason. You had forwarded me 3 or 4 articles at that time. They’re very simplistic ones. I probably didn’t read three. I only read one. I asked you this question specifically. You had formed a hypothesis statement, “We do this for,” and then there was a dash and something else. I followed that template and created my hypothesis.

Another important thing you were telling me was, “Don’t prod the answers. Don’t suggest. Let them give the answer.” The hardest part during the interview was to shut up and let the customer or the interviewee talk. Those interviews were the ones that told me that this probably is a good idea, but then there’s another need that people are still waiting for.

Sometimes, the hardest part during an interview is to just shut up and let the customer or the interviewee talk. Click To Tweet

I remember a couple of conversations at least where the last thing that the person I was interviewing said was, “That sounds like a million-dollar idea.” In my mind, I thought, “I hope tens of millions.” That was validation of the fact that people who are in my industry who are in similar roles to me are thinking about the same problems that I have thought about, and they don’t have any solutions for it. Will they pay for it at that time? They did say they would, but you can’t take their word to be the truth at that time because some of them may not even be the decision makers although they’re influencers.

Small companies’ CEOs have to be convinced that this is a good value for the money, but now, we have crossed that path. Sitting here, I can’t tell how we got to this point. It has been on the shoulders of a lot of other people like you who have been CEOs of small companies who have given me 2 to 3 hours of their time without any reason, just believing in my idea, “Tell me what you want.”

I applied to YC. I didn’t make it there, but then people from YC are still in touch with me. One of them, for no reason, reached out to me and gave me a lesson on how to do email marketing. Until then, we were not doing any of that at all. All those things have had a role in how we got here. That’s a thought that came to my mind that was important that I thought I would share.

That’s a good anecdote. That’s a testament and a validation. We all read about these approaches, especially in books like The Lean Startup. Eric Ries and others have promoted this topic and the idea heavily. When Google and other companies want to launch a new product, they always test it. They always go out and see if it’s viable or not. The reason I wanted you to share your story is a validation.

It’s not something that people do only in the big companies. It’s more important for founders to do it in early-stage and smaller companies because there are a lot of stories where founders have invested 3, 6, to 12 months or even 1 to 2 years. At the end of two years, they have nothing to show because they went about building the product based on what they were thinking versus going and talking to the customers and seeing if it’s a valid idea or not.

The process has made me a lot humbler in the sense that when you’re saying that, I’m thinking about all those founders who put their heart and soul into it. You believe the idea. You go after it. You build it. It’s important to make sure that you validate your idea. Plus, some of it has to do with a little bit of luck, timing, and things like that. I have an immense understanding or feeling that those who didn’t make it were not fools. That’s one of the biggest learnings I believe from the process.

There have been so many ups and downs where in the morning, I’m thinking of something. In the evening, I’m thinking something else. Six months down, I’m like, “Maybe I should wrap up.” Suddenly things pick up and happen. This process has taught me that I’m here probably on their shoulders and those who did not make it were not fools.

Those are truly humbling and inspiring words for sure. We’re switching gears here. With every guest of mine and whoever comes on the show, we always go deeper into a go-to-market success story and a go-to-market failure story. Specifically in your case, I was thinking it would be a good insight sharing for the audience if you could walk us through how you landed that first customer, all the challenges that you had to go through, and the disbelief, “Is this the right thing? Am I doing the right thing?” You eventually got that first check. Walk us through that process.

When I initially imagined this idea in my mind with no coding experience, my brother-in-law who you know well went through four things. His brother is also into programming and all that stuff. They said, “There’s UX. There’s UI. There’s a back end and a front end. You don’t know any of this stuff. Know that’s where you will start. There are better people who have done it many times.” They were coming from the right place in their heart. It was good advice, and I was going against that.

To start with, there were doubts. I’m trying to code. I would ask everybody who walked into my house, “Are you a back-end guy or a front-end?” That’s all I knew. Some of them would say, “I’m a back end.” I was like, “Let me talk to you later.” That’s where it started. I hired anybody who would walk into my house while I was learning or trying to build the product.

Trespassers would get a demo. That’s how it was. I give a lot of credit to the initial people around me who never discouraged me although they saw a crappy product in the beginning. When I showed it to my brother-in-law, he was like, “I wouldn’t show this to investors,” instead of saying, “This looks like crap,” which is how it looked like. That’s where it started.

You asked a very deep question. On November 27th, 2020, I had this conversation with Dave Hadden who runs a company called Pro-ficiency. He told me, “Free only takes you so far.” I thought that was very condescending. My ego got hurt. I told him that day that by January 2nd, 2021, if I don’t have this ready, I’m going to quit. I closed the doors from December 16th or 14th onwards for about twenty days. I have two young kids. They were two and a half and one and a half at that time. I told my wife, “I’m not coming out. I’m sorry, but this is it.”

By January 2nd, I built it. I texted him and said, “Dave, the MVP is done.” That’s when I reached back out to the people that I interviewed to talk to them, and one of them said, “That’s not what we want. If you build something for vendor selection, that’s where I want to use it. February 15th is when I want to send it out.” That gave me a month and a half. Here I was coding. This is the second round of coding for a month and a half to build a completely new product. I never believed that I would build it. I did not.

I thought that I would probably get somewhere in the middle and get somebody to help me or hire a programmer, but things happened such that I got to that point. Every week, I would show the progress to this first customer of mine. Her name is Audrey. She would say, “This looks great.” For me, it didn’t make any sense. I kept building, and she kept saying, “This is great.” Initially, we had people enter data into the cloud. Now, everything is automated.

Let’s take one step back. How did you find and get Audrey to sign up? That’s a critical point.

Audrey was one of the people that I interviewed in June 2020. I interviewed her. She was one of the nicest people. She answered a lot of questions for me. I had all the questions lined up, and she answered all the questions for me. She was one of the ones who ended up saying, “That sounds like a million-dollar idea.” I had no idea who she was. I opened LinkedIn. I searched for clinical operations professionals. I sent a message to whoever showed up. She had these fireside chats. Once I knew her, I started getting to talk to her a little bit and participate in anything that she would do.

That’s how I found her, and that’s how we kept in touch. I said, “I built something.” From June to December, I don’t think we talked. In December, I talked to her and said, “I might have something ready for you that I want to show you.” When I showed it to her, that’s when she said, “That’s not what I want. I want this.” That’s what I built. I told her, “If I build it, will you use it?” She was like, “I’ll use it if you want to cut down my analysis time by 80%.” That’s what she thought it would do, and I built it. I started building it.

On February 14th, Valentine’s Day, or the day before, I was showing this to my family. Some of them were like, “This doesn’t look very good.” The day before the product release too, they gave me so many improvements that I did overnight. We released it the next day. When I released it, I caught this because the vendors had to put their data in. At 7:00 PST, I released it. At 7:19, I got a call from one of the biggest vendors who was invited through that platform telling me, “What are you doing? Why are you increasing the amount of work? You’re asking me to enter all this on your platform. Why would I do that?”

He gave it to me left and right. He put the phone down. I texted my first customer and told her, “This guy is going to call you. Can you handle it?” When she talked to the vendor who was supposed to enter his data, he said, “This is a lot of work.” She said, “Does it seem like a lot of work? That’s okay. You don’t have to bid.” That’s exactly what she told him.

He called me back, and we figured out a way. We wanted to meet the vendor beyond halfway. We created a method for him where he can upload the data pretty quickly. Another significant lesson was you have to add value to both sides. You can’t add value to one side and ignore the others. That’s how I found my first customer, built the platform for that customer, and released it, the initial feedback that we caught, and learned lessons from it. We immediately identified the big holes in the platform.

B2B 52 | Clin.AI
Clin.AI: You have to add value to both sides. You can’t add value to one side and ignore the others.


Was it a paid pilot or a free pilot?

Free pilot. I wasn’t even thinking of money at that time.

At what point in time did Audrey decide to pay?

We did our first one and then had a second one. They immediately had another requirement. That’s why I say timing. They had another requirement, and then they went through the platform again. Once they went through a platform for the second time when they were at the tail end of it, that’s when I had that meeting with another small company’s CEO who was introduced to me by a mutual friend. He was least interested in the presentation. He was like, “Did you get paid?” That was his question. That night, I wrote this thing. I got paid on July 30th, which is a day before my birthday. I thought I had forgotten, but it looks like things are fresh in my mind still.

That was your first customer who cut your check.

It was Audrey. It was the same company. They did another vendor selection. The vendor selections take 3 or 4 months. We did the first one starting in February. In March and April, they had another one come up. They did that one. We got into May. May is when I floated the idea of getting paid. June is when they approved it, and then it takes 30 days to get paid. On July 30th, we got paid.

That was a 3 or 4-figure ACV at that point in time.

4 or 5.

Earlier, you mentioned that you are at possibly a six-figure ACV.

Our Annual Contract Value per customer is more than six figures. What I was alluding to before was getting to a revenue per year of seven figures.

That’s a great go-to-market success story. Thank you for unpacking a lot of actionable insights for the audiences here, but as you and I know, it’s not always up and to the right. I’m sure you must have experimented and tried different ways, going to events, sending emails, or doing cold outreach, and things have not worked. What is a go-to-market failure or a three-month experiment that you tried and didn’t work out?

You look for solutions and talk to people, and people suggest solutions. One of the solutions that came up was, “Why don’t you use these marketing companies that can find vendors?”

They’re outbound agencies and cold-calling agencies.

It’s not cold calling but rather people who can email, use LinkedIn for you, and find those clients for you. One of the suggestions came from the CEO of a huge company. There are a lot of people in the industry, but it’s hard to find who does it, especially in the pharma world. It was a challenge even to find them. I found this person who has been in the industry for twenty-plus years. She worked with some huge labs. I invested in that for three months, and I felt that there was nothing coming out of it.

As a founder, when you start a company, you probably have the messaging the best. When you haven’t done something, it’s about experimenting. When a marketing agency starts this, they have to send some emails, see how it goes, send something else, and tweak it. I don’t know if an outside agency has that commitment, or maybe I found the wrong agency to work with, but I found that after three months, I was not hitting any of the goals.

One of the problems that I had was they wanted to put something out there on LinkedIn. They said, “This looks like a nice image. Let’s put it out there.” I remember she posted it on LinkedIn, and I had to remove it. Maybe some of this is my weakness too. I don’t want anything that doesn’t look good because whatever goes out there is representing my company. You don’t want to put something out there so that people will start looking at it or clicking on it.

My point is I don’t think my mindset and this marketing agency’s mindset were aligned because I didn’t want to put whatever comes to my mind out there. It’s not about the number of clicks for me. It’s about quality and messaging correctly. I don’t think they were getting it, and it’s not their fault because it’s me who should have done that job, which I eventually did.

B2B 52 | Clin.AI
Clin.AI: It’s not about the number of clicks. It’s about quality and it’s about messaging correctly.


That’s an example of how the LinkedIn strategy or the email strategy didn’t work. I was in analysis paralysis mode for a long time, “What am I going to post on LinkedIn?” I finally started posting on July 10, 2023. In the few weeks that I’ve posted, I’ve at least had three companies reach out to me telling me that they enjoyed the way I’m using my personal expertise because I’ve worked on the sponsor side, and now I’ve become a vendor. They have enjoyed seeing the push, and they’re very authentic.

It’s early days, but whatever feedback you get is valuable in the early days. I’ve been encouraged by that. What results does it generate? We will have to wait and see. There are a couple of good leads that have come through, but we will have to wait and see if they turn into anything. I feel like at least I’ve found my voice on LinkedIn. Something didn’t work. There are a lot of other things than LinkedIn, but at least I figured out my voice of what I’m going to say on LinkedIn about my company, which I don’t think a marketing agency can do for you.

That’s a critical lesson. Typically, once a founder has found a playbook for a go-to-market, outbound, social media, or SEO, then they can delegate and offload from the data responsibly, but you cannot offload something that you have not figured out and expect an outsider to.

You asked me for one failure, but too many failures are coming to my mind, including salespeople that I’ve hired. Somebody gave me the same advice that you’re saying. When I was hiring the salesperson, they said, “Do you have a repeatable sales process that you can give this salesperson?” Initially, my thought process was, “Salespeople are motivated enough that they will sell because they’re going to make money out of it. That should be motivation enough,” but what I’ve realized is it’s a lot more than that. There are no clear instructions about how to go about the process with eyes closed where you have Step 1, Step 2, Step 3, and Step 4 clearly defined. The wheels will be spinning, and they will be in the same place. It’s not their fault. It’s the founder’s fault that they did not put the procedures in place.

Kudos to you. By training, you are an engineer. You were on the technical side of things, but given how passionate you were in this problem space and how passionate you were about solving the clinical trial gap and the automation piece that was missing, you took it upon yourself to learn, first of all, doing customer discovery, validation, and sales. You’re putting yourself out on LinkedIn and finding your voice. The biggest takeaway and message is if you’re committed, passionate, and persistent, there will be challenges, failures, and a lot of areas where you have no experience, no confidence, and no belief, but if you’re out there for a long duration, you will figure it out, and things will align.

That’s one lesson that I’ve learned. My mind always goes back and says, “Why couldn’t you do this one year back? Why couldn’t you start posting on LinkedIn? Maybe you could add a couple of more customers or a few more of whatever it is.” Things happen at a time. That’s one thing, but the other thing is the biggest lesson that I have from that is to try. It may be right, wrong, or whatever it is.

There are so many different channels for identifying your potential customers, and you may try one because you’re comfortable with it. That’s one area that I still feel like I’m behind where I don’t try because of fear of failure or because I don’t know the area well enough, fear of it not working, or fear of what people are going to think if they look at a certain email a certain way.

Something that I have learned is I’m not that important. There’s so much going on out there. I don’t think people care if I put a bad LinkedIn post out there or send an email unless it’s a horrible email, which I’m hoping I don’t send out. If it’s average, you will get a chance to improve. People won’t remember your average email and hold it against you. At least, that’s my belief. If it turns out not to be the case, I’ll learn. At least, that’s what I’m still trying to tell myself every day. I’m still learning. I’m not even close to accepting my weaknesses or faults yet.

Bring it home. We are almost close to the finish line. What advice would you give to your younger self? You did mention that. I’m pretty sure you’re going to echo it and re-emphasize it, but I would love to hear it from your words.

The one thing is you don’t know where you can go unless you start. That’s one. I had never in my life thought that I would build an application. I have a team, but when I started, I was building this application. You never know where you can go. You get your feet wet and then figure it out. If it’s not for you, you will find out. I’m going back to the same theme. Although as daunting as it is, it’s important to give it a try. The worst that can happen is that you will fail. I don’t think it will take that much time for you to realize that this is not working. You have to back yourself to do that.

For example, in go-to-market, there are so many ways to find your customers. At least in my case, I didn’t try a lot of those because I wasn’t comfortable with them. It’s getting comfortable, getting started, not worrying about what the result is going to be, not being afraid of what people are going to think about it, and thinking about whether I’m going to get a customer with this or not.

As long as it’s not hurting somebody and as long as I’m being true to myself and putting a message out there that I believe will resonate, that’s a good start. If it doesn’t resonate, you will find out pretty quickly, and then you can change. If it still doesn’t work, then you will change. If it still doesn’t work, then maybe that’s a bad idea, and you move on to the next one.

As long as it's not hurting somebody and you're being true to yourself and putting out a message out there that you believe will resonate, that's a good start. Click To Tweet

Let’s end this on a high note. I loved the conversation. Good luck to you, Kalyan, and Clin.AI.

I appreciate the time that you took for this episode. I know a lot of work goes into it. I thoroughly enjoyed it. Since the time we talked, I kept texting you the updates even when I got the Vice interview and all that stuff. You’ve always been a sounding board for me to run ideas by and also give me advice because I don’t read books. I rely on people like you who read the books and then give the significant points from it. Thanks for your help. I enjoyed this discussion. I’m looking forward to where this company takes me.

Thanks once again and good luck.


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B2B 51 | Go-To-Market Engine

B2B 51 | Go-To-Market Engine


“Sales development becomes the connective tissue between the marketing team and the sales team and even beyond.” This is what the Founder and CEO of Tenbound, David Dulany, highlights in today’s episode. Joining Vijay Damojipurapu, he takes us deep into the world of sales development at Tenbound and how it weaves into their solid go-to-market engine. Tapping into the three-pronged content, community, and events, David shares how he sets these pillars into motion along with the challenges and constraints of doing them. Tune in to learn more about how David started his journey in the industry, equipping you with great lessons on leadership and go-to-market along the way.

Listen to the podcast here


Building A Solid Go-To-Market Engine With David Dulany

It’s great to have you take time and tune in to the show. I’m grateful for all that you’re doing. Hopefully, you are enjoying the show and spreading the word with your friends and community. This is yet another great guest on the show. I have with me David Dulany who is the Founder and CEO of Tenbound. Welcome to the show, David.

Thanks for having me. I’m excited to dive in.

We always open the show with this question, which is how do you view and define go-to-market?

Go-to-market is the prevailing term right now. The way that I look at it is busting silos, so integrating marketing, SDR, sales, customer service, and product development into one unified go-to-market team. It is also making sure that your handoffs and touchpoints are customer-centric so that there’s one journey for the customer as they’re going from a lead to a customer to, hopefully, a lifelong subscriber.

I like the way you touched upon the holistic view, which is very cross-functional. It’s all the way from product to marketing to sales and even customer success. I like that. That’s key. Something else that you did mention is ensuring that there’s a good handoff between these functions, especially from marketing to sales. Within sales, you have SDR and BDR, account executives, and then the customer success for onboarding. You did mention the handoffs. In theory, that’s how we want to do it and ensure that it’s a good experience for the buyer, but more often than not, that’s not the case.

We are using a go-to-market structure that is from the industrial age in the past when we were broken out into silos and didn’t have a lot of great communication across the entire team. That’s changing a lot, especially with more forward-thinking companies, especially in the software space. We generally work in the software space. You’re seeing more cross-functional coordination and support now with companies that are accelerating growth. I think it will continue.

There is more awareness that, at the end of the day, the buying experience has to be smooth for someone to see value and purchase. It also depends on which segments you’re serving and so on. You have this micro and small business where the sales cycles are shot and things happen fast. That’s more for the sales.

You also have the product-led growth where the hand, the onboarding, the signup, and everything has to be smooth. You have the enterprise sales cycle, which is more complex. It can go anywhere from six months if you are good. It may be even three months if you have nailed it down, but it’s extremely rare. More often than not, it’s 9 or even 12 months. The handoffs can be a pain. It’s not easy to manage those handoffs.

You see more even positions being created at companies that work cross-departmentally. There’s a rise of another term, which is revenue operations. In theory, it works all the way across the backend to create the infrastructure to support alignment in that way. You’re right. It depends on the market, the company, and the products. There are so many variables. It’s creating it for your company and what’s going to work best for you.

Let’s zoom out a bit. Let’s get a bit more personal. Why don’t you share your story, your career journey, what brought you to what you’re doing today, and who you serve?

It has led up to this point because I came up in sales development specifically. I was in sales for a number of years, selling sales training, which was interesting. We had to walk the walk of what we were doing. I then got into the tech industry and started the first sales development program at Glassdoor, which grew from just myself and a couple of other people to this huge team. I got a front-and-center view of how this alignment and how the whole go-to-market team would work together. Sales development becomes the connective tissue between the marketing team and the sales team, and even beyond, to learn from customer success.

Sales development becomes the connective tissue between the marketing team and the sales team and even beyond. Click To Tweet

Building up those programs and understanding the potential there was interesting to me. About seven years ago, I started consulting and helping companies do that alignment. I coached and trained their sales development teams, and Tenbound was born. We continue to work as advisors for go-to-market teams to help them with their growth. We also do a lot of events to support the community and to help learn and grow in these topics.

That’s an interesting journey that you have over there, especially with Glassdoor. I’m always curious. I always had this question. I’m sure a lot of the audience will also have this question. Glassdoor is an employee review and feedback about a company and the workplace. What is the role of sales at a company like Glassdoor?

I started there when it was starting to go-to-market. They had started to commercialize. In the first couple of years of Glassdoor, it was building up its user-generated content and making an interesting destination for job seekers and companies that wanted to learn about what people think behind the scenes.

We’re all familiar with Yelp, Trustpilot, and the various review sites that are out there. Glassdoor took it from the angle that beyond the boardroom door or beyond the glass door, you want to know what’s going on at the company. The best way to do that is by getting anonymous reviews from people who work there.

Once there was enough traffic coming in from the user side and enough interest from the employers to create a two-sided marketplace, then it became monetization. To your question, initially, they started giving the employers the ability to edit their profile and make it more interesting to the users that are on there and post jobs for people that were looking for jobs. That was a package that the salespeople would then sell.

One thing I do want to mention is that they always made it a priority from day one that even if you bought a package as an employer, you could not delete reviews. I had some very interesting conversations as one of the first salespeople and SDRs at Glassdoor. You would call employers and they’d be like, “What is this? I’ve never heard of Glassdoor.” They pull it up and there are ten 1-star reviews. They’re like, “Why would I want to promote this?” That was an interesting conversation.

I can go deep into all these topics, but we’ll save that for another day. You are the CEO of Tenbound. Tell us about what Tenbound is and who you serve.

Initially, it was helping people figure out their sales development program and doing advisory and training with it. It has broadened quite a bit because sales development is a hot potato at a lot of companies. It swings back and forth. Sometimes it’s managed by the marketing leader. Sometimes it’s managed by the sales leader. If it’s struggling or there are issues with it, it will go back and forth. Companies will sometimes outsource their entire SDR team. There is always this constant flux happening.

Since we’ve had a lot of experience and a lot of expertise in the area, companies will come to us and be like, “How do we optimize and manage this program?” We’ll work with them as advisors to do that. The other side of the business is we put out a ton of research, content, and things like this where people who are interested in the topic come. We work with sales technology software providers to advertise on Tenbound as a sponsor for some of our events.

Your primary customers are anywhere from early-stage startups to more mature companies who need services around the SDR function.

Exactly. On the smaller end, usually, once they get into a situation where they have a director and it’s a more mature program, they sometimes will have us come in and do training if they need help with that, or coach their high-potential leaders, for example. It’s usually those smaller companies that are trying to figure out sales development.

On this show, I have the good fortune of interviewing not just the go-to-market leaders but even founders. You happen to be a founder and a leader in the go-to-market world, specifically the SDR world. Some of the questions that I have for you will not be just go-to-market. I’m even curious about how you built Tenbound and how was the early go-to-market motion for Tenbound. That’s of interest to the audience.

This is going back seven years. I had always wanted to be an entrepreneur. I’m from the old days where you get a corporate job and you work until you’re 65, and then you get a gold watch. That whole world has completely blown up at this point. I always wanted to be running a company and be out in the wild. I was between jobs and started to pick up some consulting work with friends and people that I knew in the industry because I had been around for a long time. They said, “I need help with my sales playbook,” or, “I need help training my SDRs.” That sustained to the point where I have a very supportive spouse. I was like, “It’s different, but let’s go for it.”

We started it. At the same time, we started doing the events. That opened up another revenue stream and started from there. I started with services. If you’re a bootstrap company and you don’t have any investments or things like that, then you start with services. You use revenue to pay your bills and to grow. It’s a different way to do it.

What I took from that early part of your go-to-market was you are reaching out to your network. It was mostly getting business from people who worked with you, who knew you, or who sent referrals your way.

That’s correct. I was starting to do some content marketing. This is a long time ago. This was seven years ago when it was a thing. It still is, but starting a podcast, doing webinars, trying to get featured on other people’s webinars as a thought leader, and stuff like that. We’ve never had an explosive inbound lead engine in any way, shape, or form, but there have always been enough inbounds coming in. We always want more inbound leads.

People found out through these content marketing things that these services were available, and it grew from there. As soon as we started to get results for customers, we would get case studies, quotes, and pictures. We were able to demonstrate that this service is helpful. We were like, “Here’s the logo. Here’s the person talking about it. Here’s a case study.” Having that proof that it’s an effective solution was helpful.

You mentioned besides the services like coaching, consulting, or even doing SDR services for startups, you also started going down the path of organizing events. Explain the thought process. Some context for you and the audience here, I operate my own boutique go-to-market consulting, specifically in the area of product marketing. It’s clearly challenging, especially if you’re a solopreneur or a sole owner, trying to do services, and coming up with events is not easy. How did you go about and handle the time, energy, resources, and constraints of doing services and events?

I look at it two ways. This is back in 2017. I live here in San Francisco. There were a lot of events happening. There were non-vendor events. There were user conferences. It’s happening. I went to a guy who was running events and said, “Why is there not a sales development conference that is very specialized in the SDR world?” I’ve gone on a different tangent, but he was like, “The juice is not worth the squeeze.” Being naive and coming up, I figured 1) We could have the event pay for itself through sponsorships if it was effectively marketed. 2) We would establish Tenbound as a brand and a thought leader in this little micro niche that we’re in. It acted as a marketing mechanism for Tenbound.

We took a bet. It could have exploded in my face, but it worked well. The rest is history. How? It’s a grind. Being an entrepreneur, you eat what you kill. If you don’t work, then your family goes broke. That’s not very good. It’s different. If you’re working hard in a corporate job and you’re playing a different game, there are pluses and minuses to both. As an entrepreneur, there are some big pluses and big minuses. In any event, if you want to be successful, you have to work your face off.

Being an entrepreneur is a grind; you eat what you kill. Click To Tweet

You used the term we. It looks like you had folks, employees, or freelancers at that time who helped you put together this event.

My wife gets roped into all these things although she has her own business, which is very successful. She can’t escape me because I live here. She was instrumental. We had a few part-time employees on what I call the media side of the business. The media side is labor intensive. You start as remote contractors. Everything is digital. We had an office briefly before COVID, which was a WeWork space. It’s fluid these days. You don’t need to have a lot of overhead to do these things.

I want to bring it up in this context. I’ve been studying solid go-to-market engines and how the go-to-market leaders, be it the CMO, CPO, and CRO, build the go-to-market motion, especially the CMOs and the CROs. Typically, it’s three-pronged. It’s a combination of content, community, and experiences/events. Those are the three pillars that when done well, you have a solid go-to-market motion.

I’m seeing inklings of that happening over here. You got the content piece, which is the podcast and the webinars way back. You have the event that you started. I know yours is coming up pretty soon, the GTM Revenue Alignment event. You start events. I’m sure there must be some thoughts in your head somewhere about building a community around the people you serve as well.

We do. We have a Slack group called The Pipeline and Revenue Community. Everyone is welcome to join. It’s a free Slack group. There’s a step-up called Tenbound Plus. Everything is a plus these days, like Disney+. You can get Tenbound Plus, which is a very modest subscription, and get unlocked access to all the secret files, training, online courses, and stuff like that. The community is a huge part of it.

One thing that’s interesting is in our advisory work, we’re working with people who are trying to solve problems every day and trying to figure out the best go-to-market strategy and tactics that become content. It’s always relevant because this is what people are trying to figure out. We can have a position on making something helpful for them. The content engine feeds on itself.

Thank you for sharing your early go-to-market and how you built Tenbound. You also talked about how you built the events and then layered on the community and the content pieces. Those are all in line with a solid go-to-market engine. Kudos to you and your team for that. On the lighter side, how would your friends and family describe what you do?

I thought about that. My sons would say sales development. They don’t know what it means. I probably say it about 100 times a day, so they’ve heard that. Beyond that, people might think I’m some kind of a consultant or a sales trainer. I’m not sure.

In your firm, you do consulting, advisory, training, and events. It’s not easy. What do you enjoy across those 3 or 4, the best that gets you going?

If I could spend my whole day, it would be content creation, especially editing and curating information. That’s where I enjoy doing things. There’s what you enjoy and the passion that you have for something. Every day, it’s interesting and fascinating for me. I don’t know if I’m just a nerd about sales technology and go-to-market stuff. It’s always interesting. There’s also the practical side of making a living and making the business successful. I try to meld those in the best way I can.

On a personal note, even I enjoy content creation. Content is my thing as well. Double-clicking on the question I posed earlier, consulting is a bit of a strategy and tactical stuff. You got the advising, which is more on coaching and teaching. There’s a blur that happens, which is different. It uses a different skillset. You don’t have full control over the activities.

Events are a whole different ballgame. It’s more of relationship building. There’s a strategic piece where you’re bringing the sponsors, but then there’s also the execution piece, especially leading up to the event, dotting all the I’s and crossing all the T’s. The details have to be worked out solidly, day in and day out. That’s an entirely different stress factor. Which ones do you thrive among all those activities and tasks?

It’s interesting. The tech industry has been going through a hard time. We have shifted a lot from the very high-level and tactical consulting to more advising. I love advising. I love people who are coachable. I’ve been through a lot. I’ve seen a lot and I’ve been around for a long time. If they listen to what I’m saying, take the advice, go and use it, and then come back and say, “That was great,” or “That didn’t work,” etc., I love that.

I’m working with a guy who was promoted to take over a large SDR team. He had used some of the strategies and tactics that we put together and knocked it out of the park. He was crying when he called because it had been genuinely helpful. I’m enjoying advising right now, especially at the high level with the CMOs and VPs of sales. It’s very satisfying for me.

In terms of advising the structure, is it more like you have maybe in-person workshops and then you have ongoing weekly or biweekly calls and coaching calls?

Yeah, exactly. We’ll usually do an overall assessment of the situation. That’s initially how I had started the consulting work. It is the classic consulting assessment. I’d be like, “What is going on here?” We’ll then produce a report with 3 or 4 main priorities to work on. Some of them go on for 3 to 6 months of implementing those, and then new priorities come up.

Were those assessments free or do you charge for those assessments? Were people willing to pay?

I charge from day one because it’s a lot of work. I’ve got quizzes, self-assessments, and things like that that people can take, which is great. Digging in and figuring out what’s going on takes a lot of work.

Let’s get into more of the fun stuff and the more parting advice and insights to the audience even more so, not that you have not done that so far. We are switching gears a bit over here, more on the go-to-market success story and the go-to-market failure story. If you could share any of your clients’ go-to-market success stories and failure stories, which one would those be?

The success story is more fun. We talked about the initial conference that took place. It was a huge gamble because I had no idea what I was doing or anything like that. Sometimes, your hunch and your instinct work out and it’s great. A lot of times, it doesn’t. I’ve got a lot of those stories too. That one was the zeitgeist of the moment where there were a lot of new players coming into the sales technology space. They had funding. They wanted to get in front of potential clients.

On the flip side, there was a lot of interest in sales, SDR, and marketing. People wanted to get together in big rooms and learn stuff. It worked well. We ended up doing it all the way up until COVID. It kept growing and expanding. That’s another story after COVID. That was a big success. A lot of that was luck because there was no research, customer interviews, and none of the stuff that you’re supposed to do. It was like, “This is a good idea. Let’s do it,” and it worked. I’ve got a million other stories.

One go-to-market ongoing failure is we are always asked, especially back when tech was growing, “Do you know any great SDR managers? Do you know any great directors? I need SDRs.” People are constantly coming to me before the downturn. I was like, “We have to monetize recruiting in some way. There is so much energy behind this.” We tried job fairs, virtual job fairs, career building, and getting contracts made. We threw so many attempts to stop short of becoming a recruitment company. We tried to somehow enter that space and monetize that, and it didn’t work.

Those are all valuable lessons. We learn from all those failures as to which ones work and where we don’t want to be spending time and energy. Looking at your website, I see a couple of case studies. One is around People.ai, how they used Tenbound SDR advisory to grow a massive pipeline. Something else that caught my attention is Nitro which grew SDR source opportunities. Without sharing too much of the confidential stuff, can you share what are the success stories and how you and your team played a role there?

Our real sweet spot is if the SDR program is suddenly transferred to the marketing team. I’ve found that CMOs and VPs of Demand Gen, for example, have never been SDRs. They’ve had some experience in managing those teams and things like that, but a lot of times, they need a lot of help and advice to make it work well.

What is the reason why it’s getting transferred or moved over to the marketing side of the house versus the sales? Historically, that’s where it has been.

This is controversial, but if you look at it, sales development is a top-of-funnel marketing function that creates a pipeline that’s then converted to sales by the sales team. Logically, it should report to marketing so that they are in lockstep from a go-to-market perspective on the campaigns, events, and all the different things that marketing is doing.

B2B 51 | Go-To-Market Engine
Go-To-Market Engine: Sales development is a top-funnel marketing function that creates a pipeline that’s then converted to sales by the sales team.


For a variety of reasons, especially the name Sales Development Rep, most of the people that get into that want to be salespeople. They have full-cycle salespeople. Logically, it reports to sales. The sales team is waiting for the output. They want the results of the SDR team. They’re not necessarily involved in the upstream enablement of the program, which is marketing.

Coming back to Nitro and People.ai.

People.ai was a perfect example. The program had been bounced around between sales, marketing, outsourced, etc. It was handed the keys to the head of marketing or a high-level marketing individual. He was like, “What do I do with this? I see the value in having this team. We need help. We need inbound leads and follow-up support and make sure that’s optimized. We need outbound. We can’t just rely on our inbound for everything. How do I do this?” When I hear that, it’s like music to my ears because we’ve done that so many times. It can be super helpful in that case.

With Nitro, they had a very accomplished sales development leader who’s got an amazing reputation and following in Silicon Valley. She was shorthanded as far as having the vision but not having the actual management horsepower to execute. They used Tenbound to fill that gap and make sure that everyone was staying on track and hitting their numbers.

People would be coming to you, especially since you have advisory services, coaching, and consulting as well. For what 1 or 2 go-to-market skills or strengths do people reach out to you? For example, “This is something that David is strong in. I need to reach out to David and get his thoughts and input.” What are those 1 or 2 areas?

If there is conflict within the go-to-market team. In other words, the classic one is sales doesn’t think that marketing is sending enough leads or the leads are not good or unqualified. Marketing is saying, “We are sending a ton of leads. Here they are. We’re spending all this money. Sales are not following up.” If you hear that, we can unpack that pretty quickly. The SDR team is the connective tissue between these two functions. It needs to be effective and efficient in converting demand to sales. If anybody is struggling with that, give me a call because we could help.

B2B 51 | Go-To-Market Engine
Go-To-Market Engine: The SDR team is the connective tissue, and it needs to be effective and efficient in converting demand to sales.


The final question I have for you is if you were to turn back the clock and time, what advice would you give to your younger self?

I tell my kids, “Don’t wait to buy real estate. Buy real estate and wait,” but that’s not relevant to this show. It’s good advice though. If I could go back, I would start the entrepreneurial journey a lot earlier. You don’t need twenty years of experience in an industry to then go and start a company. Everybody knows that. They see these 22-year-old guys who are already millionaires or billionaires. If you’ve got that entrepreneurial itch and you feel like you’ve got enough skills, try it. Go out and try to sell something. See if you can sell it. If you can, keep going. I would start there.

I am completely on board with you. That’s what I tell my kids, “The way to find out how you can monetize is a super skill. The sooner you learn, the better. They’re not going to teach you in school all those things. It’s up to you to figure that out.” That’s one thing. Something else that I’ve noticed, especially given that I host a lot of folks on my show and I reach out and talk to a lot of people, is there is a growing trend. The confidence level is so sky high among high schoolers, as well as folks in undergrad where they experiment and do their own startup while studying. I am completely on board with your advice. The earlier you start, the better, and the fewer things that you have to worry about. It’s always a great learning experience.

As you get older, you’ve got more commitments and more financial burdens, like kids, and stuff like that. When you’re footloose and fancy-free, that’s the time to do it. The other quick thing I wanted to mention is from a go-to-market perspective, do your research before you start product development. You’re the expert on this. Do not ever create something because you think it’s cool and you have a hunch that somebody might buy it in the market, and you’re confident about it. I’ve done that so many times. It’s the most basic advice in business. Make a prototype and go out and try to sell it. If nobody wants your product, cut it and start something else. That sunk cost fallacy is a killer.

B2B 51 | Go-To-Market Engine
Go-To-Market Engine: Do your research before you start product development. Do not ever just create something because you think it’s cool and you have a hunch.


Thank you for your time. This was a wonderful conversation. I’m sure the audience got a lot of insights and things to unpack here. Thank you. Good luck to you and the team at Tenbound.

Thank you. I look forward to talking with you again.


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B2B 50 | Factors.ai

B2B 50 | Factors.ai


No one arrives at being a founder without having the experiences that helped shape them. For Srikrishna Swaminathan, being the co-founder and CEO of India-based startup, Factors.ai, is a product of a rich career journey. In this episode, he joins Vijay Damojipurapu to share his story—from starting with FMCG sales to investment banking and eventually landing at InMobi, where he found his entrepreneurial spirit. He shares valuable lessons he learned from each phase, highlighting the importance of understanding customer needs, mastering time management, and gaining financial insights. Srikrishna also reflects on his time at InMobi and how it equipped him to found Factors.ai, a company that specializes in helping B2B marketing teams drive more revenue. He dives deep into Factors.ai’s unique Product-Led Growth (PLG) approach and also shares success stories with mid-market and SMBs and insights into early-stage go-to-market strategies. Srikrishna then rounds out the conversation by emphasizing the importance for founders to have a clear vision, which eventually spreads out to the company and leads them to success.

Listen to the podcast here


From FMCG Sales To Factors.ai: Go-To-Market Lessons With Srikrishna Swaminathan

I have the pleasure of having Srikrishna Swaminathan, who is the Founder and CEO of India-based startup, Factors.ai. Welcome to the show, Srikrishna. I’m happy to have you here.

I’m very happy to be here, and thanks a lot for making time to talk to me.

It’s my pleasure. Let’s go right into the meat of the conversation. How do you view and define go-to-market?

Fundamentally, go-to-market is you have to know based on your company, what you are trying to sell, who you are trying to sell, and the stage of your resources. For example, a company with a very large amount of resources, a company that is funded, or a company to bootstrap the go-to-market strategy or how you define go-to-market changes very differently.

At the crux of all those things, how do you approach your customers? How do you interact with them? How do you showcase to them that you exist? This is a value you provide, and how you convert it into the sales funnel is what fundamentally defines go-to-market for us. While this is a broad definition, the nuances and the tweaks around it are based on your segment, who you are selling to, your ACV, your stage of the company, and your resources across the board.

Maturity levels as a company also because a company with a three-year-old life would be very different from a company with a ten-year-old life. How even they approach a go-to-market and how in terms of who does the selling, who doesn’t do the selling, and who activates that. For example, for early-stage startups, it’s founder-led and that is a very different go-to-market than, let’s say, when the team comes in, when people come in, when processes set, and those things. It’s very different from how the company will change it.

I like the aspect where you emphasized a lot about the resource constraints and what stage of the company that you are in. Typically, I hear that characterized or mentioned by founders where I have founders on my show. They’re the ones who would mostly focus on that versus if it’s a guest who is either a marketing leader product or a revenue leader at a more mature company. They would focus more on the alignment between product, marketing, sales, and customer success. I know you are implicitly referring to that alignment as well, but I appreciate you focusing on the stage of the company and where you are or where your mindset comes to making the best use of your resources.

That’s a very good point, what you mentioned. It’s not that we don’t look for alignment. We don’t look for how multiple teams come together from a go-to-market. Once you’re selling a product, once you have something in place, you know who you target. Everything else needs to come together because otherwise, you won’t make yourself aware to the market, which is marketing.

Once you make them aware, you have to bring them into your sales funnel, which is there, which is a part of sales, part of performance, or demand capture, which is there. Once you bring them into the funnel, the customer success, the onboarding, and the product teams, everything also needs to work with a feedback loop running around this. I’m not taking away from that. The key thing here across the board is also that one aspect is very clearly resources.

You might have a $10 million funding versus you are a $3 million funding versus you just started up, etc., all those things. The second aspect is maturity. For example, I have seen the same go-to-market being approached very differently by second-time founders than approached by first-time founders. I have seen this evolve very differently from a company, which is one year old. They might still have the product they would have been selling. They would have 100 customers, etc., compared to a company that is 3 or 4 years old and how they approach that. That is a very soft aspect of things but it makes a huge difference in how things get executed, which people get to play, how people are recruited, and employee satisfaction. Many other things come into play here.

The point you mentioned reminds me of or surfaces for me where there are different nuances even among founders, the type of technology, and the product. There are founders who are very comfortable in building in public right from the early days. There are founders who are so engrossed in “stealth mode” which has been like you need to rewind 5 or 10 years ago for that concept. Building stealth mode for 1 to 3 years and then in year 4, you realize, “I wasted all my resources and I need to shut down my company.” That’s been less of a norm of late.

To your point, building in public versus stealth also depends on the technology, the product, the IP around what you have, and so on. Let’s switch gears. Let’s go to the big picture and focus on your life and career. Why don’t you describe or quickly narrate what has been your career journey so far and what led you to what you’re doing now?

I’ve been very lucky. I was born late. My parents were almost 50 when I was born. I was born in Chennai and spent my schooling in Chennai. I came to Bangalore for higher education, undergrad, and Electrical Engineering. I spent a couple of years coding, but then realized I have a heart for management. I got into one of the B schools in India called IIM in Calcutta. I spent two years there. After that, I jumped into the FMCG world. I spent a good part of two years in almost rural villages and towns across Andhra, Kerala, Orissa, and also Western UP. That’s where I spent a lot of time learning. Being on the field, sales and marketing is a very different experience and that’s something that taught me a lot.

It also gave me a lot more maturity at 23 or 24 years old. I came back to Bangalore, got married, and joined a banking startup, an Eastern banking firm. From there, I moved into another startup then called InMobi. InMobi was one of the first unicorns in India. They had raised the large fundraise from Softbank and Softbank was not a well-known entity at that point in time.

Unicorns were even more rare in India. Companies like startups, 3 or 4 years old, becoming a $1 billion valuation was a very big thing at that point in time. I was a little bored with banking, but I was also thinking, “If I have to make something big, a splash, or have an interesting life, I have to be in a place where action is.”

InMobi was one of the few startups where both from a cultural aspect and a large market aspect, it showed great promise. I started with business development and sales within InMobi. Over a period of time, I started up and built a very large P&L business unit also within InMobi called Affiliate Business, the whole affiliate and exchange business, $100 million P&L. Thankfully, with InMobi, I found my Cofounder, Praveen Das, who was part of the product team. Both of us overlapped for seven years at InMobi.

My third Cofounder is Aravind, who’s my friend from college days. He was my college classmate. He was at Google. Later, he sold his first startup to Freshworks, and we all got together to attack the problem around account intelligence, ABM marketing, and how to identify, activate, and attribute marketing around B2B companies.

That’s from our experiences both at Freshworks and InMobi. This is something which we found as a white space and we jumped in and started up. We were lucky both in terms of funding. It was pre-pandemic so the funding space was also pretty good. We also took another small round of funding and now, we are growing pretty rapidly at 160-plus customers. We are doing pretty well.

In hindsight, will you be able to connect the dots and figure out what are those experiences that led you to what you’re doing now? If I had to dig in maybe from your time when you were at Dabur, right after your MBA, clearly being in the field being the fast-moving consumer goods, that helped. What were your takeaways from that experience being at Dabur?

One thing is it exposes you to the actual on-field sales. If you are in an FMCG sales company and if you are in a beat sales mode, for example, there are multiple geographies as well. You can look at, let’s say, Dubai or any other larger markets or even city-led urban markets and all those things. Most of the sales happen through modern trade where there is bulk buying, discounting, and then you also give pricing features, etc.

When you are on a company like Dabur, which is predominantly a very good rural portfolio in Ayurvedic items, which are there apart from Josephs and a couple of others, it’s a rural-oriented company in terms of what they sell. Second, it’s also more of a poor rural-oriented company, which, compared to India, is pretty widescale.

That is a huge difference between Western India and Southern India in terms of how urbanization hits, how per capita income hits compared to other countries or other states, and all those things. Per capita income is much lower, which is that. When you are thrown into the middle of one rural area and also in terms of how you need to activate your sales items there, how do you need to penetrate those markets? How do you need to price your markets very well? Also, understand the psyche of people on what they are looking for. A ₹10 or ₹1 change would be a huge difference for them. ₹1 is a little more than a cent.

That’s some experience that, at 23 years old, was a very different experience to have. It teaches you how lucky you are and how privileged you are. It teaches you a raw sense of scale in terms of there being so many villages to cater to. You have to be present in every village, but the output quantum from each village would be much smaller.

It teaches you a lot of frugality. It also helps you teach planning. For example, you have eight hours in a day and one of the first things which you are put through as a sales trainee in these companies is you have to take a bus in the morning, go all the way to each and every village, sell at least ₹10,000 of items and then come back.

This means you have to be on time for the bus. Once you are there, you have to be on time when the market opens. You have to finish your job fast, then move to the next village. Many things can go wrong. I’ve seen floods. I’ve seen some political leaders dying and closing down because of that. There are some districts where you can’t go on certain days, where there are black days and other things. All this helps you. Also, you can see something like each and everything for you to make the product work. You have to find the right assortment of goods so that you can make your target.

That is an experience for an early management trainee. You can take that away into each and everything, whether it comes through product-like growth, how you price your product later, how you distribute the product, how you manage your costs and efficiency around it. How do you discipline your own life in terms of how time matters?

For example, you can’t sell for anything beyond 6:00 in certain markets because 1) There won’t be any electricity. 2) The market also shuts down. You have to leave before 6:30 in the morning, and if you don’t get up and do it, the buses will leave. There is only 1 bus every 2 hours. All these things were an amazing experience for me and personally, it transformed me a lot. I’m happy for it.

All the insights and the lessons and learnings that you mentioned, which are humility, working with discipline, and resource constraint, all of these things made you the Founder that you are now at Factors.ai. Switching gears, so you were at Dabur and then you moved into investment banking. What is the driver behind that?

I had interned in an investment bank during my MBDs. When I graduated in 2009, none of the banks were hiring and nobody was doing anything. FMCG companies were the only ones that were hiring a little bit. Thankfully, I entered the FMCG line, but I wanted to get married and my wife was in Bangalore. I had to move back to Bangalore because being in an FMCG role traveling five days a week might not have made sense for her to come and for her to move back. I had to move back to Bangalore. A couple of friends were working at Mission Bank in Bangalore, which was a pretty good firm.

Allegro Capital was there. They used to work with pharma and a lot of healthcare hospital firms. That’s what they were doing. I got into investment banking. It was a two-year experience. I also did one of the first deals with the startup at that point in time over a period of two years. It’s a very different experience both around numbers and in terms of from a financial services perspective. How you look at clients, how you solve client requirements, how you need to be on the toes at each and every point, and how you can make some mistakes, etc. As with any junior associate or someone there, I learned through mistakes and it was a great experience, but one thing I saw there is direct business-to-business pitching.

FMCG sales are very different. You have a product that has a brand. You also know someone would need a toothpaste. It may not be like whether it’s someone who’s going to buy a ₹5 toothpaste or a ₹10 toothpaste, but he’s going to buy something. As long as you can come as somewhat like you have a brand behind you and you have a trustworthy name behind you and you can give credit, you’ll be able to sell it.

B2B 50 | Factors.ai
Factors.ai: As long as you have a brand behind you, a trustworthy name behind you, and you can give credit to it, you’ll be able to sell.


A ₹10 item to a ₹100 item, anyone can sell. It’s either now or tomorrow, the item is going to get sold. Investment banking or even B2B sales at a very different level is much different. You have to make the need happen. You have to understand when is the right time to nudge or push them into the conversation.

Everyone, and especially anyone who raise funds or mergers and acquisitions, it’s high stakes. It’s something like that life’s work getting into a certain value. There is a cash payout. There is always a doubt whether it’s an opportunity cost or I’m missing out on something bigger and other things. Managing all these emotions, nudging, and also getting people around multiple stakeholder games where different age groups or sets of priorities, everything comes into place. That was a great experience, which I got from that as well.

One great aspect is I got to work with some of the founders who were college seniors running an eCommerce logistics company at that time, delivery. They were running out of cash and they wanted to raise their Series A. I helped them through that. Around that time, I figured out startup was the place I had to go. I have to be there. Incidentally, that company from a Series A at somewhere around a $20 million valuation. Now they listed and become a public company at almost more than $4.5 billion valuation. Great experiences, but that also made me move to InMobi at that point in time.

I was going to InMobi, and that’s where you found your cofounders as well. It looks like InMobi is a place where you also find what problem to tackle. Why don’t you talk to us about your experience in InMobi that shaped you to be the founder that you are now?

If I had the chance, out of college, I wouldn’t have wasted 2 years of coding, 2 years of MBA, and then a couple of years between banking, and 8 years across multiple places into learning work and getting maturity. I would’ve said that anyone should first go and work in a startup. The quality of the work is amazing. You might be dealing with smaller sizes and different kinds of problems but you can jump into anything and find something to do and shine there and solve or fix problems, then move on to something and learn something from that in a startup.

A mature startup gives you a little more safety. They also will pay you good salaries. At the same time, you also have a team and you have more problems to solve because scale breeds scale. You’re still agile from a mental standpoint. I would advise anyone to work in a startup at any point in time. InMobi was one of the growing startups in India.

There was the pride of being the first unicorn, which was coming out and we have to at least go big into this thing, most importantly, since it was a mobile ad tech company. It was fundamentally a company that used to run mobile ads for customers. There should be advertisers on one side and publishers on the other side. It was like gaming companies, news apps, etc.

Advertisers used to be eCommerce companies. You could see both sides of the ecosystem growing. For example, there were gaming apps, publisher apps, and other apps that were startups on one side. There were also eCommerce startups, which were right from Flipkart, Myntra, and others who are trying to grow their business in terms of app downloads, conversions, and others happening.

You are seeing the whole digital transformation in India as well. The geo moment in 2016 when Rilancio came into the place, and then there was the whole transition in 2013 and 2014 into the Android smartphone era. Also, the rapid growth and scale-up in terms of funding, which is coming into India. Many other new companies starting to grow within this thing. You were able to see business models being made right in front of your eyes. That was the InMobi experience.

In my capacity, I was lucky that I started with sales. During sales, I found a gap and opportunity in the market, saying that affiliate businesses that are growing where it’s not direct advertiser to publish a connection, but that is the intermediary business, which could also be rapidly scalable. This is something that I pitched internally to the InMobi founders. They let me start up the internal group and build that business unit fully.

I started from zero and it went all the way up to a $100 million-plus business. It was one of the most profitable units within InMobi. One that gave me good exposure in terms of management, building your team, and building your own internal startup, but within the umbrella of a company that was there. Also, there is recognition within the company where you can go and meet a lot more people. You can get to talk to a lot of people, etc. That helped in multiple ways. It gave me safety and comfort. It also gave me a good name. It also helped me find my cofounders, etc. Unforgettable experience. InMobi was such a good place for me and I’m always grateful for and obliged for that.

It sounds like even though on the surface, on paper, it sounds like Factors.ai is your first startup, but you’re like a second-time founder. You’re not a first-time founder, given that you started a business in InMobi.

It was more or less like that because, in InMobi, I was given a brief. I have to either do $5 million or I wouldn’t be doing that. I have to do something else. That was an up-and-out situation and it put good pressure and other things. Most importantly, when you work through a situation where it’s a young company, it’s also a startup and you see so many business models built around you, the natural itch towards something like you have to build something on your own comes.

When that comes onwards and you’re also in a company that is growing in agile and a lot of smart people are around you, you also start looking for problems that you see. Two things. 1) You can also solve for it as a company, as InMobi, trying to solve for it and then build a business around it. 2) You would also look for problems like if this thing need not be solved by InMobi, can I build a company to solve it?

If InMobi or Freshwork faces this problem, then can this problem be something that we can extrapolate through induction for thousands of other companies, solve the problem and can we make monetary gains around that? That’s the fundamental itch around any startup game. You identify a problem, you feel that you are personally hurt by it, and try to understand and figure out whether it’s going to be something that is a business or something like a service. Is it going to be a short-term pain, a vitamin, or a painkiller situation? You gather around people to go and solve it if you find it good. That’s what ended up happening with our own journey.

I would like to note we are switching gears a bit over here. You were at Dabur FMCG. You were an investment banker to some extent and then you were at InMobi and now, your own startup founder. How would your family members and friends describe you? Do they know what you’re doing and how would they describe you to others?

As I mentioned, my parents were a little old. As long as I was coming up to college and getting a job, they were pretty happy. They weren’t sure what I was doing at any point in time. They were traditionally asking am I happy? Am I healthy? I remember my father talking about this thing. He’s from a much older generation. What he understood very well was my FMCG world. That’s something that he understood. You make something, sell it, and profit out of it. All the companies that I worked on after that didn’t make any sense to them. Banking was like, “Why should they approach you? Why can’t they talk directly to the investors? What are you doing in the middle?”

InMobi was looking fancy. Also, as he came in, he was saying, “What are you guys doing?” Essentially, he wasn’t able to understand the mobile ads ecosystem, monetization, etc. My startup, he also keeps asking, “Are you guys profitable? When are you guys going to be profitable? When do you have to return your loans, which you have taken from your investors?” He doesn’t understand this thing, but they are confident that I’m working in a team, employing a lot of people around me, and doing something that looks respectable and clean. That’s what they’re happy with.

My wife, on the other hand, is an engineer at Microsoft. She understands a lot of the tech. She sometimes asks, “Is this good? Are you guys bending the limits in terms of engineering?” On her scale, when she’s at the ChatGPT team versus what we do, the scales are very different. It’s also a good perspective that you get at home and can also share it.

What you mentioned as to how your family, especially your father, described and saw you and your transition versus your wife. There’s a generation gap and understanding of the different and evolving business models. It shows how quickly our industry is moving and the different types of monetization in business models. Switching gears here, let’s get into more of Factors.ai, the growth, and the go-to-market. Where are you at? You don’t need to share confidential information, but you mentioned you’re growing rapidly. Where are you at in terms of the number of employees, revenue, and customers with Factors.ai now?

We’re at 45-plus employees. I wouldn’t be able to share the revenue numbers, but we are at 160 customers as we speak. We are adding almost our customers every day, which we are working on. It’s been pretty rapid growth where we moved from 30 customers all the way up to 160 customers now. From 35 customers to 160. We have raised funding as well both at a seed level and a pre-series A level. We have wonderful investors in the form of Elevation Capital, Emergent Ventures, and Stellaris. All Elevation and Emergent are US-based while Stellaris is an India-based fund.

That’s a testament to how good your founding team is, the problem that you’re tackling, and the confidence of the investors. These are top-tier investors who have invested in your company. I’m looking at your website. You’ve gone the PLG route. You have offered a free trial and then your pricing is all the way from $0 to $99, $499, and then the professional. How did you arrive at this? You must have mentioned, gone behind, or talked to a lot of your prospects and customers. Walk us through that process.

To start with, we are never PLG. We never had a free forever plan. We never even had a $99 plan. Our base plans started with $499. We had experimented with something, but at the minimum level, we were selling at $799 on a monthly basis. What changed is one thing. You want to expand your market and there are two ways to expand your market. One is you can go more and more enterprise. You start by saying that $800 a month and become more of a $25,000 or $50,000 annual. Very large enterprises are there, which is one thing or you go on the other side where you see the problem which you’re doing has a huge benefit in the mid-tier to SME market, which is very large.

With the pricing, how you bring in the value props, which you offer, time to value, which you have in terms of the thing, all of these things change. We found a large value in more of the bottom. We were able to take on that use case and for that, we tweaked both the product and the pricing. What you see is the outcome of that.

Now, almost every day, 5 to 10 people sign up for our product. They start immediately with a free trial. At the end of the free trial, we give them options. Either you can go into a paid plan with customer success and other features or you can remain in the free forever plan, which is also there. We have people also constantly ping us through either Intercom or through our Slack channel support saying, “I’ve seen this. This is all good. Can I sign up for a plan? This is what I want to remain here. This is what I want to use.”

People are referring to us customers. A lot of things are happening and that’s where we have found the growth momentum as well for us to say that you start slow and you start with a certain good funnel where you let people experiment with the product. Let people see value in the product. Once they do that, it’s far easier for us to sell and build on top of that.

That is an upsell journey, also. That is a very clear upsell methodology where we say, “You add these things on top, then it becomes easier. If you want to do a lot more, then you have to expand your pricing plan. That’s something that we have built into the product. The most important lesson within this is never to be green. Respect customers’ need for value. These are two different things.

This is something that everyone professes. Look at what value you are driving to them. You have to always pitch for a higher value or if you have spent or if you have done something of so much value, you have to push for a higher rating. I feel the reverse where if you can show value to them by helping them easily enter into your product, see the value, and recognize the value, then you make a customer and have a lot more time to prove to them. That’s one thing.

If you can show people value, then you make a customer and you have a lot more time to prove to them. Click To Tweet

Second is also the ability to see value in terms of ROI. Once that is there and once that confidence is there, they’ll get like, “This is a no-brainer deal for me.” Once a no-brainer deal comes for you, once you add other things on top of it where you say that this extended feature gives you this, you have to pay so much more for this thing, they are far more willing to pay for it. It’s not a question on the mind. They don’t treat you as a salesperson or a vendor who’s asking for this thing. They treat you more as a partner saying, “He has delivered value for me, hence, accepting his recommendations and this thing and adding on top of it is going to be easier for me.

For the benefit of the readers, who is your ICP and what is the problem that you’re solving? How is that problem defined? How did that evolve since day one?

Fundamentally, we serve for B2B and SaaS companies. Any company selling to other businesses or SaaS companies are companies that are fundamentally selling to other business software companies, other manufacturing companies, any healthcare firms, etc., is our direct target. Within these companies, our ideal customer profile is companies that have less than 500 employees.

We look at companies that are more ideally less than $100 million in revenue because, at that stage, a product like ours would make sense. Spending with product market fit or spending early on ads. It’s either ads or they should have a website at least running. It shouldn’t be a company where it’s in stealth mode where the founder is trying to have a dashboard and trying to sell with a service plus a product mode. That doesn’t work.

The product founder has moved beyond the ten design partners and now starting to sell to unknown companies. That’s where a product like ours makes sense to the level where it becomes, let’s say, a $100, $150 million company where there is a certain established marketing team and there is a sales marketing team. A buyer journey needs the ability to identify accounts and convert from marketing to revenue. That’s a use case.

We have exceptions on both sides. We have very early-stage companies also working with that. At the other end, we have multiple listed companies and enterprises that are also working with us. I would say more than the size of companies and ICPs, the use case that you solve for is what makes the difference. The fundamental use case, which we solve for and what we propose to our companies is you work with us, we’d be able to increase your pipeline by 20% to 25% within the first three months.

More than the size of companies and ICPs, the use case that you solve for is what makes the difference. Click To Tweet

How this happens is by providing them with account intelligence. In B2B companies, the unique thing that happens is nobody randomly visits the website. It’s not an entertainment website. It’s not CNN. Anyone who’s coming and visiting your website and reading your blog or your resources is someone who’s keen on the problem you solve or has a problem and he’s looking for a solution based on what he’s looking at.

He doesn’t look for the joy of reading a blog on, let’s say, account-based marketing. That’s one thing. The second thing in B2B and specifically increasingly across the board in B2B, including whether you see legal services, software, or manufacturing, so many things, the website is becoming the most critical point of any buyer’s joint.

Every digital company is not an afterthought like, “I have a website. I also do sales.” Website is the fundamental way where you have the branding, where you pull in customers. Nobody’s going to buy your product without coming to your website. What we do is use this as the fulcrum and bring in data from multiple first-party, second-party, and third-party sources. We bring in data from your CRM.

We bring in data from your marketing automation email systems. We have your website data. We bring in data from your channels or your review sites, etc. We integrate all this data, and build an account score to say, “These are the accounts that are intent on buying your product.” There might be hundreds of visitors or thousands of visitors on your website. These sets of accounts are the ones that have a high intent on buying from you. That’s one thing.

Second, how do you activate them? You can run campaigns for them, send emails to them, send a gift card to them, or send a cold call to them. You can do all these things and then bring them back into the funnel and convert more companies. Why this fundamentally helps generate revenue list, sales, and marketing are both on focus. That is marketing. You want to spend only on things and channels that are converting.

They want to focus on which accounts can immediately convert to a pipeline rather than someone who is just a window shopper. We solve both of these in a single platform to say that I help sales teams go after accounts that matter. I help marketing teams to go after campaigns and channels that bring in these accounts. We bring both of those together.

The problem that you’re trying to solve for the marketers and sales team is about intent and buyer resolution to a large extent. There’s also an overlap with the ABM tech stack, like the 6Sense and Demandbase. How are you different from them?

6Sense, Demandbase, and multiple other ABM platforms are fantastic products in the first place. They were built for a different era. Both of them are more than ten years old. What that fundamental proposition at that point in time is like that is Google display ads. You have a list of accounts. Give me the list of accounts. I will use LiveRamp, Bombora, Intent, and a few other databases, and show ads on the general display, which is there.

The users would eventually see your ad. Let’s say IBM is showing an ad and they have a white paper. Download the white paper and they’ll come to your website. That is a lead generation, which happens, and the sales team goes after the lead generation. This is built for companies that are generally enterprises, very large companies, large deals, and most importantly, where marketing and sales work in silos.

That is where you run display ads and then you have the sales team going after leads and conferences or direct in-person meetings and other things. What we are looking at is the democratizing of ABM. A large ABM platform makes a lot of sense for enterprises. What about mid-market to SMBs, which also want to do the B2B market?

For example, if an ad agency wants to bring in customers, he’s not going to go into the club or go somewhere to a conference and expect customers. He’s going to run ads or run small-scale ads, Google search ads, or a LinkedIn ad. He’s going to do a post. He’s going to do content that is going to be SEO optimized to bring in customers or bring in customers to the page.

It’s the same thing with, let’s say, a small-scale SaaS company or a startup trying to build this business around or even a small IT services company trying to build for mobile app development or something of that sort. All these companies are selling to business. They need an ABM-to-ABM model and they can’t afford to spend on a large platform and an enterprise, only a lead generation model. They want to work on systems which is there. That’s one thing that has changed over a period of time.

The second thing is the whole process of selling and marketing as well. Do you spend on multiple channels? No. The sales and marketing loop is very closely integrated. It’s not something like the marketing teams work on product content material and product marketing material, and the sales team goes and converts the accounts and other things.

Both of them are integrated where the product does search ads, LinkedIn ads, and other things. Immediately, the signup happens. People go through your product or even take a demo of the product, and then they sign up with your system to either use a free trial or talk to your sales guy and then convert immediately.

This close feedback loop is shortening. This is more coming into the way mobile app or B2C customers used to work. That is a B2C verification of B2B in a sense. That is multiple channels are suspended. That is a shorter lifecycle and people want to also test and then improve immediately this thing and there is a constant feedback loop. You need a very different product in terms of how it is built.

For example, in B2C in mobile apps, there used to be companies like Amplitude which used to do attribution. Our vision is to bring that product to the B2B marketing space for a different segment of customers. What we are seeing is the market expanding into a different segment of customers which needs a very different product in terms of the ability to make segments and cohorts of users and then target them, then reach out to them, and then expand revenue. That’s a segment that we play in. We coexist with the likes of larger ABM platforms because every company would also have an enterprise play and a PLG play. We are not set up for an SMB-ish kind of thing. We target the SMB-ish market or a mid-market to SMB market.

B2B 50 | Factors.ai
Factors.ai: The market is expanding into a different set of customers that need a very different kind of product in terms of the ability to make segments and cohorts of users and then target them, reach out to them, and expand revenue.


That’s why PLG makes sense for you as a go-to-market motion for sure.

We don’t put our own product.

Switching gears again. Go-to-market has both success and failure stories. You’re seeing both sides of the world, not just for yourself, but even for your customers. If you can share with the readers both a success story and a failure story, that’ll be great.

One is very early in the before PMF was hiring salespeople. We had a good set of youngsters working with us. We set up the email domains, asked them to send email blasts, and worked with them to run emails and those things. It was early before PMF. The product didn’t have the market fit. The market was not fully ready. We were blasting it. People used to come to check out and come into demos. It never used to be a high-intent demo and with the conversion rates, everything falls off the track. That’s one thing. Second, as a mistake, which a lot of people continue to do is cold emails.

There are multiple changes that are happening in the market. One is all email providers are becoming anti-spam and anti-promotion. Most of your emails end up in the promotion tab or in the spam tab, which is there. Second, people themselves don’t read multiple emails. The email open rates, email reply rates, and generally, cold email reply rates and other things are very abysmal.

Still, you have so many people and salespeople swearing by it to send more emails to see whether they’ll get something in the funnel. Earlier, it’s like, “I sent 100 emails. I get two replies. Now I send 500 emails and get maybe 4 replies.” The scale to conversion doesn’t even make sense. With more automation thrown in and more ChatGPT and others, it becomes more like there isn’t any sense in finding together how it’s going to work at all.

On the other hand, the ability to find intent advance and also managing energy. That’s another thing, which is about the same email thing. If a sales guy has to talk to 100 customers or even email 100 customers, he’s never going to personalize. If he’s going to talk to only 20 and knows this 20 can convert better, he’s going to be far more personalized. He has the sense to approach them better. He would also do a LinkedIn connection. He’ll do a messaging. He’ll do a personalized video. He’ll do so many things to make that work.

If these things were in there, people wouldn’t even make that. Hence, knowing who has intent, having a product market fit, and then trying to set up your sales or go-to-market motion to attack this problem is far more energy-efficient and far more remunerative in terms of your growth and other things. The return on effort is amazing. That’s a mistake we made early in our careers. We learned through it. We figured our product fit through our problems in terms of selling.

B2B 50 | Factors.ai
Factors.ai: Knowing who has intent, having a product market fit, and then trying to set up your sales or go-to-market motion to attack this problem is far more energy-efficient and remunerative in terms of growth.


We were like, “Why should selling be so difficult for B2B SaaS companies?” Why should it be so difficult for me to do ABM to ABM sell without spending a lot of money on Google display ads or something of that sort? That’s where our product idea also generated. Our GTM mistakes ended up with our product growth.

That’s a classic story of when you are so attached or dialed into a problem, you try to come up with a solution and you are living your problem firsthand and your product became your solution and now, you’re in a better place to market your product to similar personas. That’s a great GTM failure story. How about a success story? It can be either yours or any of your clients.

I remember a second-time cofounder. There are two companies that did this very well. One company, which is Sprinto, which is a SOC-compliance product. Second is RocketLane, which is a customer onboarding software company. Both of these companies were second-time founders. The first one, they thought through. Everyone calls it luck or something, but the ability to time the market is also the founder’s intuition to know what happens.

They were able to come into the market when a lot of software SaaS companies were coming out of India. Data compliance and security compliance became very important. You were having larger trends coming in. They built a similar company and have been able to blitz scale into a growth which was there. That’s something that grew into almost becoming more than $5 million. It’s like a case study that every startup needs to follow. It’s almost in the same time period.

Another company is RocketLane. They started building a community before they had a product. They said, “We are going to solve problems for this set of customers, this profile of customers within this customer onboarding team and customer success team.” They worked backward to say, “Let’s build a community of all the customer success and customer onboarding team.” Once you build a community, bring them together, give them content, talk to them, and have that interactive feedback loop to understand their problems. This fed back into their product.

Once you build the community, bring them together, give them content, talk to them, and have that interactive feedback loop. Click To Tweet

They were able to hit product market fit much faster. Both of these are amazing case studies like, “How do you prepare to get your go-to-market and make this thing work?” That’s good learning for us as well and for the rest of the community. One thing about a startup is to know where you are going to get the direction. Velocity and displacement, everything takes care of it. If you get the direction wrong, a lot of things can go wrong.

The energy that comes to my mind is it’s almost like a golf ball or even a flight path. If you change one degree or there’s an error of one degree early on, that one degree translates to tens of degrees in where you land or where the ball lands. Fantastic. In both cases, it sounds like Factors.ai played a big role in their success.

They are customers of ours. That’s one thing that helps me also understand. I don’t think I would’ve played a role in this thing. They became larger companies when they started using our product. That’s how it worked. Most importantly, we were able to learn from them. Also, we were able to see how the switch to product market fit happens. Once you have PMF, how fast the growth happens is very visible to us.

Two questions for you, Srikrishna. One is, what are your 1 or 2 GTM super skills, superpowers that people wonder about or contemplate and say, “Srikrishna is strong in this. Let me go and chat with him?”

If I look at my personal strengths, I’m very lucky. I tend to get to make good friends. People come around to test this thing. Fundamentally, one thing that I think through my experience of mistakes and my own learnings, which I can share very good inputs on, is about both in terms of early-stage go-to-market and how you start from early stages. Let’s say you have the first five customers. You have the first 10 design partners.

Next, what do you do? Which channels do you advertise on? How do you set up your sales motion? How do you set up your email motion? How do you set up your SDR motion? How do you set up your ad campaigns? How do you set up your marketing top of the funnel to the sync so that you can convert your customer’s past and then go after it?

That’s something I had got a reasonable experience on relative to the market, which is something people do come to me for. The second thing is also understanding the feedback loop in terms of how you identify early team members and early founders. How do you get the early system running and then building on top of that? Once you get the early setup right, a lot of things get solved for the next five years. After five years, it’s a very different problem and there’s a different scale which you have to solve for, but you have to get the early setup.

Thank you for sharing those. The final question I have for you is, if you were to turn back the clock and go back to day one of your GTM journey, maybe it’s Dabur or somewhere else, what advice would you give to your younger self?

As I mentioned earlier, I would’ve joined the startup much earlier. Instead of 2020, I would’ve started up in maybe in 2012.

The key aspect or something to emphasize on and the advice to the readers would be, yes, join the startup, but join a startup that has found a product market fit. There’s also the other aspect as to what is the criteria that you need to look for that have the DNA of a successful startup.

One is like at the fundamental level as founders, you want to work with people who have your confidence and that’s something that you can very clearly seek. Once the founder has clarity in mind, it transpires into a clear vision. It transpires into more clarity like what he’s doing and why he’s doing it. It’ll also help eliminate any cultural issues in terms of people being irritable, not hiring the right people, not over-hiring, etc. All these things these things get solved for. Fundamentally, you need to look for whether you have a founder who’s mature and clear in a set. That can be issues around product market fit, early stage, late stage, or something like that.

That can be so many companies, whether it’s funded or not funded, but fundamentally even with funding-funded companies or late-stage companies, things can always go wrong. What doesn’t go wrong is you having the early founding team being very clear on their heads. If you can identify companies or people you can set with on those lines, and this is a human gut instinct, it’s like you’ll know whether that person is right or not or whether he’s confident or not. Whether he’s someone who can be a leader or not, that’s something which you very clearly know and you jump into the ship with them. Whether it’s a ship, a raft, or a catamaran, whatever it is, you can figure the way out.

Thank you so much for taking the time, Srikrishna. Many nuggets for me personally as well as for the readers on go-to-market, your career journey, and how you made the choices and decisions as to what you’re doing and who you’re serving now. I wish you the very best and I wish the team at Factors.ai the very best as well.

Thanks a lot.


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B2B 49 | Carabiner Group

B2B 49 | Carabiner Group


Your RevOps solution is here! It lies in the hands of the Carabiner Group. Today, Cliff Simons, the CRO of Carabiner Group, shares the tactics and the actions taken to lead the organization to success. Their agility and nimbleness to turn away problems once they see them coming helped their business deal with the challenging tides. Cliff also shares his GTM success and failure story. Let’s get into this episode with Cliff today.

Listen to the podcast here


Leading The Carabiner Group With Cliff Simon

In this episode, I have another great guest lined up. His name is Cliff Simon. He’s the CRO of Carabiner Group. He has a very impressive track record when it comes to go-to-market, building revenue, revenue teams, and so on. Without further ado, let’s welcome Cliff. I’m excited to have you on the show.

Thank you for having me. I appreciate it.

Let’s dive right in. How do you view and define go-to-market?

I have a different take on go-to-market and a lot of folks in B2B do in the sense that a lot of what we do in the B2B space, we’ve tried to make it fit a certain mold or what we think the traditional patterns should be. A lot of what we’ve done from a Carabiner perspective is, “How do you enable your buyers to have a B2B experience that looks and feels as much like a B2C experience as possible? What does it feel like to go through that B2C motion? How do you take away the friction very much like Amazon has done? How do you pull all that friction out of the buying process to make it easy for people to purchase?” I think HubSpot has done a fantastic job of this.

You don’t typically read through all the legal leads of a HubSpot contract because it looks like a checkout screen. If you want to read the legal leads, you have to click on the Ts and Cs. Who’s going to go and fight on the things within a Ts and Cs? You’re naturally conditioned through Apple and everything else to accept the Ts and Cs, scroll through, get to the bottom, and just move on with your life instead of doing the due diligence that most of us would do on any contract that came across our desk. It’s a little bit different from how we would think about go-to-market.

I like the aspect where you are focusing on the buying experience. I’m fully on board with you that B2B should transform itself into creating a buying experience that’s very similar to the B2C world, like the Amazons and Apples of the world. They have revolutionized, for sure. You mentioned over there the click-through and getting started on using a service or a product. There are a whole lot of activities and tons of things that happen for a buyer to come to that point.

There’s so much that has to happen there. That’s why we’re seeing such a big surge in PLG. We’re enabling them to tell us what behavior they want to walk through. They’re enabling us to understand the pieces of technology they want, how they want to deal with it, and what that experience looks like. We’ve been informed because we already know from the Amazons of the world what that experience should look like. We now have to sit back and think, “How do we take that process and engineer it for our specific use case?”

I’m sure we’ll dive deep into several of those topics in our conversation. Shifting gears and going big picture, why don’t you walk us through your career journey, what you’ve been doing, what led you to what you’re doing, and who you serve at Carabiner?

My background is about two decades of go-to-market experience selling in the mid-market enterprise. I started my career off at a Fortune 20 company, highly ranked rep there, did well, and then they took what was making me six figures a year and turned it into a $5,000 quarterly bonus. We all saw the writing on the wall and it was a pretty big exodus at that time. I have spent many years in SaaS. This is my third time doing a 0 to 10, but 0 to 15 before. That’s my first time doing it from the C-Suite.

As far as what we do at Carabiner and how I got here, most people don’t anticipate going into Revenue Operations or RevOps as a career choice. I was that sales leader who enjoyed getting into the data, understanding the why and how, and giving good data feedback to my team. Even for bringing that up to the board and the executive leadership team, this is why things are happening. I had a deep passion for it. Falling into the lucky circumstance of running as a twenty-year-old who is starting a company and getting a chance to help build something from the ground up is intriguing to me.

I got to join Carabiner in its early days when we were just a salesforce consultancy. We made the shift to RevOps as a service in early 2021. I took that very first Revenue Architecture Course that Winning By Design had put on. Jocko was leading it. It was right after the first day of class that we changed all of our positioning and messaging. We went out and picked up a couple of trademarks around RevOps as a service. This is the future. That’s what enabled us to get a decent position from a marketing rather position in the market because it is so much earlier than everybody else did and being holistic about the customer buying journey. Trying to focus on that journey and that experience has helped us stay apart from a lot of the other folks that are coming to the fore.

You started off your journey in sales at telecom companies you are at Nu-Wave Wireless and Verizon, and then you shifted into SaaS. It’s a smart move there. That’s where all the big money is. After that, you joined Carabiner, which provides RevOps as a service to SaaS and technology companies.

A lot of our clients are SaaS. We serve anywhere from series A to D on average. We’ve got folks on the outlying pieces there, some C companies, some series E, and publicly traded, but by and large, a lot of our customers are SaaS. We also work in a regulated industry and a lot of financial services as clients. We also play nicely in the higher education nonprofit space. We’ve seen a lot of folks from manufacturing start coming out and needing services.

That’s been a nice twist from our traditional ICP. When you’re doing the same things over and over again, 80% of it is the same digital transformation, whether you want to call it RevOps or something else. It is a process. How do you look at a customer’s buying journey here, a go-to-market process to it, and only then, how do you build up the technology to meet that process instead of going out and buying all these point solutions like folks have for the last many years?

When you're doing the same things over again, 80% of it's just the same digital transformation, whether you want to call it RevOps or something else. Click To Tweet

A funny incident or coincidence was that I had a guest who made a very similar move from the other side. He started off in the services side of the house and then moved into SaaS. You did SaaS and then moved into the services side. He and I were discussing selling services versus selling SaaS are different. At least, SaaS buyers get to see “touch and feel” something versus services only after you build that trust. They speak to current customers, and that’s when they get the confidence. Otherwise, “I’m not 100% buying into what you can deliver for me.” How are you handling that challenge at Carabiner?

For us, it was building trust by building thought leadership. That was accomplished by having a lot of face-to-face interaction, whether in person or on one-on-one Zoom calls with other go-to-market leaders, finding out the pains that they were dealing with, and making sure that we were building a team that could meet that collective need. We’ve got a lot of recognition through our relationships with communities like Pavilion, RevOps Co-op, or the exclusive RevOps partners in both of those scenarios and then working well across the ecosystem.

Once you’ve proven yourself, you start building out some case studies. We were fortunate to get some larger clients very early on when we were doing some massive digital transformation projects that led to the credibility of the work that we could do. Like any small company, you leverage those and keep building. Once you’ve built up a significant body of work, it becomes a lot easier. At this point, we’re seeing 100 reviews between AppExchange, G2, and almost every single one of those. Ninety-five percent of those are five-star reviews. That’s fantastic. We want to keep that up and make sure that we’re giving that level of service to our clients.

What was the revenue ad when you joined Carabiner? That was a few years ago.

I joined in December 2020. The company was 3.5 or 4 months old at that point. We weren’t on an ARR model. It wasn’t recurring revenue. It was nascent. I wouldn’t even register as anything.

In terms of revenue, you are 5, 6, or 7 figures?

We did seven figures in ARR in our first year and then followed that up in 2022 with 4.5X growth, which was incredible. In 2023, somewhere between 10% and 30%, which is not terrible considering the market and the way it is to be able to say that we are going to grow in 2023. I’m impressed that we’re going to hit that number.

For the benefit of the readers, it’s all about the tactics and the actions that led you to this point. Three things stood out for me from what you mentioned. One is being part of communities like Pavilion, which builds credibility. Something else you also mentioned is changing the positioning and improving the buyer experience. The third you mentioned is getting the big brands, the Lighthouse clients. From sequencing, let’s dive into each of those three.

At the core, the reason we’ve done well is what we call agility nimbleness. We have always prided ourselves on being able to say, “If we see a problem coming, we’re going to shift away from it quickly out, bootstrapped, or revenue back,” whatever you want to call it. We don’t have investors that we’re beholden to, which allows us that flexibility.

I don’t have to wait until I go to a board meeting and get them to approve something, which is nice. What that’s allowed us to do around that Amazon desk deal is to take a look at our customers’ journey and say, “What are the things that most people don’t like from consultants? What things do they hate about pro services? How do we take that out of the process?” For us, that means there is no SOW.

Most companies our size and with the capabilities that we’re offering have a very strict scope of work. Meaning that if we go outside of that scope of work, there’s going to be a change order, which means you’re going to have to take 1, 2, 3 weeks for that paperwork to get approved and then paid for, etc. We don’t do that. We want to be able to be very nimble. If our clients have a request, we want to be able to acquiesce to that request so long as they understand what that may do to the rest of the project from a timeline perspective and be able to adjust to that within a matter of days. That’s one thing that we wanted to do.

The other thing that we do is we annual contracts by and large. It’s very different from most of our competitors who are out there where they’re going out to the market and saying, “You’re going to pay us for this particular scope of work. It may take 3 or 6 months.” All we’re going to do is to the letter that’s scope. Because there’s no SOW and we’re coming for the long term, we’re incentivized to build systems that we’re managing that are going to work. Because of that, our Compound methodology, instead of an Agile methodology, our clients see that work gets delivered on a weekly basis and they can understand the value that’s being presented to their organization and the impact that it’s having on a regular basis instead of us going off and building in the dark.

Part of it is how we’re go-to-market and how we’re delivering the services that we’re promising. Those two things coming together create a very different buying experience. What that meant for us as a company is in that first year, we were doing a 6-figure sale on average in 28 days. In 2022, we were doing a 6-figure sale on average in 34 or 35 days. Our ACV increased to damn near $250,000. It was a very significant dollar amount that was moving very quickly.

B2B 49 | Carabiner Group
Carabiner Group: How we market and deliver promising services creates a different buying experience.


Six-figure closing under a month is unheard of. Typically, it’s 3 to 6 months. That’s the standard benchmark, but clearly, you got something going. When you described what you guys did from a services point of view, the term that came to my mind was productized services.

That’s very much what we’re trying to do. We have four service offerings, essentially. We have RevOps as a service, which is our flagship service. It’s Salesforce and HubSpot expertise and 150 other pieces of technology that connect in those ecosystems. We have a lower-cost admin service for folks who need a little bit of help. We do an advisory service for people who are trying to understand how to think about that go-to-market, “How do I go about putting these processes in place?” We also do an audit product, which is probably our most popular product.

We do a full scope on people processes, technology, and then insights and analytics, like that data piece. It takes 4 to 8 weeks, depending on the size of the organization, but it’s a pretty comprehensive readout. On the back end of it, you’re getting a very detailed Kanban backlog of, “This is how we recommend going through and fixing your organization and the progression that we believe it should take.” It’s usually done in 0 to 3 to 9 and 18-month increments. You’re getting a year and a half worth of change laid out for you, which a lot of companies find very helpful.

We do an audit product. We do a full scope on people, processes, technology, insights, and analytics like that data piece. Click To Tweet

I would assume that most of your clients, if they’re getting to know you and want to engage you on the first service, would start with the audit.

It’s a nice way to say, “Let’s feel each other out. Does everyone like to work? What’s a good communication style?” You start building that connective tissue just like you would when you’re bringing in a regular in-house person.

All of these that you mentioned clearly improve the buying experience, which is 1 leg of the 3-legged stool that we talked about. The second leg was around being part of communities that built your credibility. That’s Pavilion.

When it comes to the community space, it’s how you go about thought leadership and how you add value without always trying to take it. For us, it’s been very much showing up consistently and helping people who have problems. If it comes back to us as revenue or business, great. If it doesn’t, we’ve helped somebody because there are just not enough people doing RevOps.

It’s the number one job on LinkedIn. 8 of the top 25 roles on LinkedIn are RevOps functions. Everyone’s trying to figure this out. We can help point you in the right direction and you don’t have to pay for it. Go and do. If you need more than that, let’s have a different conversation. That’s been us doing webinars, writing white papers, and lots of one-on-one talks like this where if someone’s got a question, we’ll just hop on and have a conversation.

It's great if we can help point you in the right direction and you know how to pay for it, but if you need more than that, let's have a different conversation. Click To Tweet

I’ve spent almost two decades in go-to-market across a whole host of industries with a whole host of go-to-market motions. Maybe something I know or a member of our team knows that can help you, let them help you and take that knowledge and go run with it. If that works, please let us know after the fact so that we can celebrate with you and say that it’s been well done. We did the same thing with our customers. When things are going well, tell us. We want to be able to celebrate with you because we want to earn the right to celebrate those milestones together.

The third piece was around getting the big Lighthouse clients and the brands.

That happened a little bit more accidentally, but maybe not quite as accidentally. We ended up working with the largest FP&A runner in the country through cold LinkedIn outreach. We work with 2 of the 3 largest collegiate athletic associations in the country. That was brought to us by one of our IFP partners because they needed somebody with the expertise to build up the systems.

Those systems are used by something in the neighborhood of 1,100 colleges and universities and represent the contracts between those colleges and universities and something in the neighborhood of 150,000 to 160,000 collegiate athletes every year. There is pretty cool stuff to get to do, and I had a lot of exposure because of it. Going after that has been cool, then being able to consistently work for good clients, knowing that a mature executive leadership or going after a very specific private equity or VC firm so we can work together has been good for us as well.

On a lighter note, you started your career as a salesperson, then you grew up the ranks and now you are a sales leader or a CRO. What does your family think or what do they think that you do for work? How would they describe you to others?

My wife comes from a medical background, as most salespeople, especially in the IC role or in mid-leadership. You tend to balance around a decent bit. That was a little hard for her to understand in the beginning. Now, she knows that I do something with software and I get paid to talk to people. It’s outside of her wheelhouse, but she gets most of it and respects it, which is good.

She knows it involves Salesforce and HubSpot. That’s as far as it goes. As far as my family, I’d say probably something similar, my friends all get it because they’re all in tech. Whether I’ve got guys in my hockey team who are Salesforce admins or SAP admins, they all get it. They’re developers. It’s not as far a stretch for most of them. On the family side, it’s different, especially since a lot of my family comes from blue-collar, “You help people and they pay you to do what?”

“All you do is just talk.”

“You talk and you help them think through things? You’re not building something with materials? There’s no actual material cost.” That’s a fun conversation.

A funny story that you shared over there was your family members, specifically your wife and other family members who come from a non-tech background, you versus your other colleagues and friends who come from a tech background. That’s a common theme that I’ve seen. When I ask this question to my guests, it always brings us a good laugh. Thank you for that. Shifting gears here, we all know that go-to-market is not just success and up and to the right always. There will always be failures as well. It would be great if we could share with our listeners both GTM success and failure stories. Pick yours, which one you want to start with.

The success story is pretty easy, considering the amount of growth that we’ve had in the last few years. It’s been crazy. Going back to that whole, people in B2B want to buy B2C and community-led growth. A lot of what we do is community-led. In 2022, 91.5% of all of our inbound and new clients came from community-led word-of-mouth or referrals. Activating and operationalizing that program has been very successful for us. In 2023, we’re trending somewhere between 85% and 90% again. It helps drive customer acquisition costs lower and it makes for a quicker sales cycle because that trust we talked about before is already inherent in the process.

Before we go to the failure story, I want to double-click on the success story. Can you share how big your go-to-market team that includes sales and even on the marketing side and how you break the responsibilities?

We have one AE who works under me. We had gotten up to 4 or 5 at one point. On the marketing side, we had one. We’re about to hire a new marketing associate. On the CS side, we do that by committee because, unlike the SaaS company, we’re talking to our customers every day because we are on the product. It’s a bit different as far as how that gets managed. It’s funny because that bleeds into what I think is the go-to-market failure, which is an inability to see what was coming down the road. This caught everyone by surprise, but how bad it got at the beginning of the year for us being over-indexed on SaaS as a client base, which caused churn.

A lot of companies went under. A lot of people got funding cut out from underneath them and things were seen as a luxury that was previously seen as a necessity just because they had their entire budget wiped out. We ended up losing a couple of clients that way. Because of that, we had to make some head counts being a bootstrap business. For us, that would be a failure having to go through that motion. Now that we’re building back up from it, we’ve learned a lot of good lessons.

From any of your client side, you don’t need to share any confidential private information, but it will be good to share a success story. What was the institution prior to when you guys came on board, how did things change, and how did it improve their go-to-market success?

The coolest ones are probably the NJCAA, which is one of those collegiate athletic associations. They purchased another consulting firm, a product that they thought was going to help handle the entire registration process of all those pieces of tech. They implemented it. Within 30 days of the implementation, they scrapped the entire thing because it wasn’t working. It’s a huge opportunity cost and the actual dollar lost.

They were working with another consultancy to look at how to fix this in Salesforce. It wasn’t moving quickly. They brought us in within two weeks, we had shown them how we would build it, started putting together the prototypes, and they signed a very long-term contract with us in which we got to build all that out, which was cool. The success story for them is that they had never been able to uncover all of the metadata that was wide within that student body.

What they were able to do is take that metadata and bring it back to the Department of Education and get a ton of grant funding because of the way that their student body is made up. Folks, on average, are on the lower side of the economic ladder. Because of that, they ended up pulling in several million dollars in federal funding. It was a cool side piece to trying to solve the problem. They were able to turn that into an economic gain for them.

That’s a big win. You did mention the breakdown of your team both on the sales and marketing side. It looks like most of your team members are Salesforce or HubSpot implementation experts.

Almost our entire company is comprised of either Salesforce or HubSpot, what we call senior consultants or consultants, and in some cases, architects. Those folks are supported by project managers, engagement managers, scrum, and some Lean Six folks. It is very process-driven.

Another cool part of the story that we should be covering is you did mention the founder of Carabiner. What is that story like? Is it he reached out to you or did you reach out to him? How did it all happen?

He had started the company already. A quick story is he was in high school and ended up doing salesforce consulting when he was in high school for an investment bank out in San Francisco. Through that process, he ended up getting an opportunity to speak at Dreamforce before his eighteenth birthday. He was seventeen years old. He continued doing salesforce consulting through undergrad and was supposed to go work for Deloitte Digital doing salesforce consulting, but got his offer letter paused because of COVID. We ended up starting the company. A couple of months later, he and I met on Slack channel, a RevGenius of all places. We met there randomly.

The first day I signed up for RevGenius was early December 2020. We had a call and very quickly led to a series of calls back and forth. It felt right. My wife’s like, “You should definitely go forward and try this out.” Originally, I came on in a fractional capacity because we do fraction in everything, then after my first full week here, it’s like, “We should make this full-time.” We’ve built a great relationship along the way.

If you had told me a few years ago that I would meet some twenty-year-old kid on a Slack channel, we’d have a company together, and we would be building this crazy thing and what it’s become, I never would’ve believed you. It feels so unbelievable. It’s like something you read in a book or it’s in a movie. It’s serendipitous that you meet somebody on a Slack channel then Slack is the number one way in which you engage with most of our client audience. It is a great tool. I love it.

People get a lot of their networking and job leads through LinkedIn, but I think it’s becoming common, especially for more of the entrepreneurial folks who are active in good communities like RevGenius, Pavilion, and others. You can find opportunities. Did he reach out to you or did you reach out to him?

I posted that I was in between roles at the time and I’ve been interviewing for Head of and VP of Sales roles at Series A companies and some enterprise-level roles as an IC to try it out and see what was going to be a good fit. I posted on RevGenius. He reached out to me that day. We had a meeting that afternoon or maybe the next day. He was originally looking for an IC. I wasn’t interested in that. I wanted to build something, especially coming in earlier.

We were able to transition that pretty quickly because of the nature of the questions I was asking him. I wasn’t asking him about, “How much commission am I going to make? How many vacation days am I going to get?” It was, “Talk to me through all your conversion rates. Talk to me about your FP&A.” The second half of my interview process for Carabiner was building out our FP&A for fiscal year ‘21. At that point, I was excited about it. The fact that I was asking business-level questions and we were trying to get to the bottom of what it would look like to grow something intrigued him.

Something that stands out or I get a sense of is you are good at sales. That’s my sense.

I’m okay at sales. There are a lot of people who are a lot better at sales than I am.

What are 1 or 2 things when it comes to the go-to-market side that people reach out to you for like, “I have this burning question and Cliff is a great guy. I should just chat with.”

Usually, it’s a go-to-market process. They’re trying to figure out how to make one piece work or they’re new in a role and they’re ingesting all this information. They want to know my opinion on it. Maybe it’s seemingly simple as sales stage criteria or, “We haven’t necessarily thought about the fact that our mid-market and enterprise sales motions are completely different. How do we bifurcate that from an actual process perspective, and then how do we cement that process difference in technology?” It ranges a wide gambit.

You are good at sales. It’s not just doing part of sales but also the sales process and thinking as a sales leader. That’s what came across right when you mentioned about you and the founder of Carabiner about the FP&A process, plus people reaching out to you for sales entry and exit stages.

What’s at the heart of that is most salespeople are not trained on how to think from a business perspective. I’m trained to think about a specific problem and how my product addresses your problem. Most salespeople are only looking at that problem in a vacuum. They’re not considering the fact that that problem might not be the biggest problem that someone’s dealing with or trying to solve that problem that might only take up one to 2% of my mind share.

B2B 49 | Carabiner Group
Carabiner Group: Most salespeople are only looking at that problem in a vacuum because the problem might not be the biggest unless someone’s dealing with or trying to solve that problem.


It might be a painful enough problem for me to care about fixing it now. You have to find out what the bigger problem is. What is keeping that person up in that area? What do they think about? What are their goals? How does that affect their career mobility? How does that affect ELT, their board, and their share price? Think about those things and how they affect their customers.

Double-clicking on some typical day in the life of Cliff, maybe it’s a week or a weekend, what does that look like?

Let’s break down a week. It’s probably easier. There’s a handful of internal meetings that I’m constantly being pulled into, whether it’s a client escalation, making sure things are going well, or just like the running of the business walking through recruitment, finances, sales, marketing, or whatever it might be. That’s probably something for 5 to 10 hours. I probably spend another 10 to 15 hours involved in sales motions. I probably spend another board five hours a week networking, talking to folks, catching up with friends, seeing what’s going on, and meeting new VCs and PE firms.

There are probably about two hours a week on professional development and learning something new. I spend anywhere from 5 to 10 hours a week vetting new technology, finding out what’s the newest of the new, what’s working well, or, “I haven’t seen this yet. I haven’t seen this in two years, let me get a refresher,” because I want to know what everyone’s using. I want to understand how well it’s being adopted and how it can potentially fit the needs of my customers.

The last piece all comes back to knowing your target customers and buyers well. We should reemphasize or highlight how important it is for each and everyone, especially you as the reader. If you want to get good at either marketing or sales, it doesn’t matter. For anything customer-facing, you need to carve out, spend time, and understand what your customer is dealing with on a daily basis. In your case, it was the technology.

I spend about the other five hours of the week talking to customers and hearing what’s going on with them. The voice of the customer is extremely important in understanding their business challenges so that we can either help stay in front of that and help lead them in some ways or make sure that we’re thinking about it. One of the things that have made us successful is we’ve got some good folks who work for us and will take the time to learn the ins, outs, and nuances of the industries and the sub-verticals that they’re serving.

B2B 49 | Carabiner Group
Carabiner Group: We have some good folks working for us who’ll take the time to learn the ins and outs and the nuances of the industry.


Typically, I ask my guests what resources they lean on when it comes to shows, books, or community. The community definitely is top of mind for you. It’s very clear.

I lean on Pavilion. A lot of the people I respect the most in the game now are there. I went through CRO school with Pavilion. I still meet with the same cohort of people that I went through that with a few years ago. We’ve met every two weeks for the last few years. That’s been an invaluable resource. I love winning by design stuff, listening to their videos, and getting a chance to go to any of the courses that they offer. The two books that I would recommend the most for Leaders is Extreme Ownership by Jocko Willink. The other would be Matt Blumberg’s Startup CXO: A Field Guide. I love that. It’s great because you can earmark the heck out of it in terms of the chapter that you need for that moment in time.

As someone who’s helping to run a small business where I have to think from a finance, BizDev, and marketing perspective and take all of that in, and I haven’t necessarily had all of those roles throughout my career, that’s been an invaluable guide to just get into the mindset and think through the problems from the way that would particularly look at it. On the other side of that, from a sales guy’s perspective, it helps me get in the mind that much better of the people and my team’s selling to.

I don’t have those books on my list, so I’m going to add those. The final question for you because I know you have little ones to take care of in the business is if you were to turn back the clock, what advice would you give to your younger self? Day one of your GTM journey.

I would learn to be more process-driven earlier on. Don’t be late. I was bad at that when I was younger. That cost me a lot of credibility with folks in leadership. Be more process driven-early on and you don’t always have to be the one that’s right. Have a little more humility earlier on. That’s something we all tend to learn as we get older, but a 23 or 24-year-old Cliff who had been a little bit more humble would have gone a lot farther.

Be more process-driven earlier on. Don't be late. Click To Tweet

The second one, you have clearly fixed it. You are on time or even before time joining the show, so you are not late for sure.

B2B 49 | Carabiner Group
Extreme Ownership: How US Navy Seals Lead and Win

I’ve got one guy on my team who used to work for Jocko, who wrote Extreme Ownership. He was a Navy SEAL for twenty years. I have a daily standup for the team and he is always the first one on the call. Even if I joined five minutes early, he’s the first one on the call. He’s like, “My goal is always to be wherever you are before you get there.” I’m like, “Fair. I can’t argue with you.”

Where can people find and learn more about you Cliff?

If you want to connect with me, find me on LinkedIn. It is pretty easy. I’m Cliff Simon. There is a little cloud in front of my name. That’s the easiest way to get in touch with me. Otherwise, if you’re in any of the communities that I’m in, RevGenius, Pavilion, Wizards Of Ops, or RevOps Co-op, feel free to shoot me a Slack message. I’m happy to have a conversation.

It’s a great conversation. Thank you for sharing a lot of the tactical advice and actionable insights. Good luck to you and the team at Carabiner.

Likewise, thanks for having me on. I appreciate the time.


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B2B 43 | Human Centric

B2B 43 | Human Centric


Success in the evolving world of go-to-market lies in embracing a paradigm shift – from company-first to people-first strategies. By placing the individual at the center of your approach, you can reach the true potential of B2B relationships and pave the way for enduring success in a hyperconnected world. In this episode, we have Nick Bennett, B2B SaaS Marketing Advisor, discuss go-to-market strategies and how they have evolved. Throughout the episode, Nick touches on various aspects of marketing principles, such as storytelling, values, and authenticity in building connections. He emphasizes the transition from B2B to H2H (human to human), where the personality and leadership behind a brand play a crucial role. Additionally, Nick shares his own career journey and emphasizes the power of consistency and showing up. He explores the importance of aligning values when selecting new opportunities and roles, and how treating marketing as part of a revenue organization leads to greater success. Nick challenges the notion of saturated channels and highlights the pivotal role of people in cutting through the digital noise. Don’t miss this episode of learning how to get ahead in this evolving industry. Tune in now!

Listen to the podcast here


From Company-Centric To Human-Centric: The Evolution Of Go-To-Market With Nick Bennett

I have Nick Bennett. I’m sure if you are active in the marketing world and/or if you’re active on LinkedIn, it’s very hard for you to escape the name of Nick. I’m sure he must have popped on your radar several times. Without further ado, let me welcome Nick. How are you doing?

I’m good. How are you doing? Thank you so much for having me. I’m excited to be here.

Same here. There are so many topics, conversations, and deep dives. I’m looking forward to it. With that, I always start the episode with this signature question. That’s what this show is all about. How do you define go-to-market?

I’ve been thinking more about that lately. I think the new way to go-to-market is people-first. Before I get into why people-first is the new way, going back to the old way, a lot of marketers have that mindset of it is a company-first go-to-market. When I think of company-first go-to-market, I think of brand spam. I think it’s more about the lead quantity. It’s all about capturing demands and transactional. You feel like you’re out on your own.

Now, the B2B go-to-market has to evolve because of the convergence of AI, channel saturation, cookie list future, and all these things. It moves to a new way, which is that people-first go-to-market, so it’s putting the person first. It’s meaningful interactions. It’s the lead quality versus the quantity aspect of it. It’s create-demand relationships, and partnership-centric as well, which is a big thing. You think about the ecosystem. I know there have been some events that have been going on recently where everyone is talking about the ecosystem, and how that plays into go-to-market today. For me, people-first go-to-market is the move for not only 2023 but beyond as well.

I completely agree with that viewpoint. I saw your LinkedIn post, which is about personalization at scale is what will matter. Doing a persona exercise is cumbersome. It’s time-intensive and resource-intensive, but not many people actually get to use it or don’t know how to use that. I’m completely on board with you on that. Here is the challenge, and this is obviously the million-dollar question that’s facing everyone.

Especially in the startup world or even beyond the startup world, there’s always the pressure of, “Give me more leads and build more pipelines.” At the same time, we all know that quality is what trumps or what works versus quantity, but there’s constant pressure because you either need to appease the leadership team or the board. There’s always this dynamic. I completely agree with you on the people first. What is your answer? How do you approach that situation?

It comes back to understanding the five principles of a people-first go-to-market. One is a story or a point of view. You have to have a point of view on something and it has to be meaningful. The second piece is values. Going back to the values of people and putting people first, it’s not transactional. It’s being transparent in having pricing on your website or having an email come from an actual person. Many times, companies send out marketing emails and it’s like marketing at XYZ company. Why can’t it be from the person that wrote that email? Why can’t the eBook that your company put out have an author page for the content team or whoever worked on it?

Relationships and how authenticity shines through are so important. We all know it’s not B2B. It’s H2H, so human-to-human, and people buy from people. It’s the partnership, the personality, and the person behind it. You need to have the leadership, and not only marketing leadership but executive leadership buy into this mentality of empowering people both internally and externally. You have to rely on having those conversations at the right time and realizing that, so many times people like to say, “This channel is dead, email is dead, events are dead, or MQLs are dead.”

It’s all about how you can turn that into a positive moment and take learnings away from it to drive impact versus saying something is dead. Every channel is saturated. How do you cut through the noise in the digital world? It goes back to the people. Everything that you do, like ABM, PLG, and inbound is ultimately still about people at the end of the day. Having people both internally and externally that can champion your brand is huge in today’s world.

The first filter, and maybe one of the key filters that one has to apply when selecting a new opportunity or a role is around the values. Does the leadership team, founder, CEO, marketing team, or revenue leadership teams, whoever they are, subscribe to this H2H mindset? That’s the biggest thing. They should not be afraid. They should be encouraging the email marketer, the customer success person, or the content creator to have their name or their stamp on that email or on the website.

I don’t want to say this is all marketing leaders or all leaders in general, but so many people are bought into the old playbook of what worked five years ago. What worked five years ago doesn’t work today. It’s just like anything. Technology evolves year after year. Apple convinces us to buy a new iPhone every single year and pay thousands of dollars for it, even knowing it’s a very incremental change. The brand has empowered everyone. Everything that they do makes us go out and buy that. You have to be bought into modern-day marketing for this to be successful as well.

Let’s switch gears. I would love to have you share your career journey with the audience. There are a lot of cool nuggets. It’ll be interesting to see. I would be interested in understanding your inflection points and where you made the transition, so bring it on.

I have a little bit of an interesting background. I played baseball all through high school and college. I went to college for Sports Management. I didn’t want to go to college, to be honest with you. My parents pushed me to do it. They were like, “You’re going to pay for it because we don’t believe that you’re going to graduate. You’re probably going to flunk out and we’re going to end up paying the bill.” I took out student loans and did my thing. I was like, “If I’m going to go to school, I’m going to go for Sports Management. I thought I would get out and be some big athletic director, sports agent, or something like that.

I got out and realized that I could go sell tickets for the Red Sox making $10 an hour. I was like, “This isn’t what I thought it was going to be. I’m out of school. I need a big boy job now.” I went into sales. It’s not tech sales. I never worked in tech sales per se, but I worked in inside sales for some tooling companies. I ran AT&T. I worked for Motorola, and AT&T was my account. Going back to the iPhone, I used to sell up against iPhone every fall. We would have to try to basically get AT&T to buy through a bunch of products.

It helped me then figure out that I was good at sales. I knew what I was doing, but I hated having a quota hanging over my head every single quarter or every single month. I came across a channel marketing role. I was like, “This is cool.” I get to work with all the partners. At the time, it was a 100% channel company, so all they sold through was the channel. I got to work on cool campaigns with that. Originally, what that helped me do was move into field marketing, because it was pretty much the same. The only difference is field marketing. You have the internal sales team channel. I worked everything through the channel. I got into field marketing and I was like, “This is awesome. The sales are my customer. I’m getting to do all of these amazing things without a quota hanging over my head, but I’m still being a part of the sales team to a certain degree.”

I never looked back. I did field marketing for tech companies, mostly in the series-B to series-D stage, for the last ten years. I went through multiple layoffs and multiple acquisitions, and one company ran out of runway. I’ve seen everything at this point, then I was like, “Let me transition into ABM.” I moved into ABM a little bit and started talking about that. I then recently did customer marketing as well. In my most recent role at Airmeet, I headed up an event-led growth, which was a new term we were trying to coin, as well as communities, social media, and this whole creator aspect.

I realized for me that people-first in the creator economy and B2B is where things are moving and this whole evangelism. How do you evangelize not just executives within companies? Executives should evangelize. I think of Sangram and all these people that are executives. That’s part of their job. What about those people that work for your company that have followings for themselves? They can become bigger evangelists and drive meaningful impact through pipelines and close one revenue.

Somewhere along the journey, something magical happened. You were not Nick who was doing a day job, but you were Nick who was doing the day job and being active on social. If my memory serves right, that encouragement or the transition happened when you were at Clari. Did I get that right?

Yes, absolutely. For everyone tuning in, I used to report to Kyle Coleman. He’s very well-known on LinkedIn. He’s now SVP of Marketing at Clari. At the time, he was heading up our sales development team, our enablement team, and our growth marketing team, which field marketing rolled up into. We were in Laguna Beach, California. We were at our revenue kickoff. He was the one that was like, “You should start posting about field marketing on LinkedIn. No one talks about it.”

It was crazy because the more I thought about that, and even in my past, so often people would just share a company post. They weren’t creating content. It’s like 1% of people would create content. At the time with 650 million users, no one talked about field marketing, what it was, the misconceptions to a revenue organization, and all of those things. I said, “I am going to do that.” I doubled down and talked about that. I tried to share my experiences of programs and things that I was working on.

I speak with a lot of not just marketers but even others within go-to-market teams and even founders for that matter. They all want to be active on LinkedIn. They know that being active on LinkedIn is the magic bullet to get more brand awareness and pipeline. The intent and desire are there, but to translate that into an action or a habit is a huge jump. How did you make that transition?

It’s all about consistency. Consistency doesn’t have to mean that you’re posting every single day. Consistency means showing up, whatever that means to you. Maybe that means showing up and posting 2 times a week or 3 times a week. At least at a minimum, you should be engaging with other people. People have to start to treat LinkedIn as a community to a certain degree. All your buyers are there. I’ve read something recently that there were almost a billion users on LinkedIn. It was 970 million or something like that. I’m sure they’ll hit a billion users before the end of the year. Think about that many people on LinkedIn. At the time, 1% of people were creating content.

B2B 43 | Human Centric
Human Centric: It’s all about consistency. And consistency doesn’t have to mean that you’re posting every single day. Consistency means just showing up, whatever that means to you.


I did read something that said by the end of 2022, they were close to 4% of people that were creating content. I’m sure as you’ve seen, it has gotten noisier. How do you cut through the noise? For those people that started like me three and a half years ago, it’s a little bit easier. If you’re starting now, you have to find like-minded people that you want to engage with and engage in their posts. You don’t have to create your own content.

If I see you posting every single day about go-to-market, I can add value there, and then I can be one of those first people that comment. I’m going to organically build that base back to my own LinkedIn page before creating any of my own content. I always recommend that now. If you’re going to get started, you don’t have to jump in and create content five days a week. Go engage with 15 to 20 people that you want to learn from every single day. I guarantee you that it’s going to pay off more than just jumping in and posting content.

That’s good advice for someone. Clearly, someone can put that into action this week or even next week. Let’s zoom back a bit and talk about how you approach go-to-market. You did touch upon several aspects around people-first. In your last couple of roles, how were you thinking about go-to-market at companies like Airmeet, Clari, and you also were at Alyce? How are you thinking about go-to-market in all those organizations?

The biggest thing is you have to think of it as a revenue organization. You can’t treat it as silos. Often companies are like, “I don’t have silos. There are no silos between sales, marketing, CS, BDR, or SCR team, but I guarantee you, every company has silos, whether you want to admit it or not. If you can treat it as a true revenue organization where marketing, sales, CS, and everyone is involved throughout that entire buyer’s journey, it’s going to be a lot more successful. Everyone is going to be a lot more willing to jump in and be a part of it versus just marketing saying, “I’m going to go drive MQLs.” Salespeople don’t care about MQLs. If you say, “Here’s how I’m going to put an extra $30,000 in your pocket for this quarter,” I guarantee you people are going to listen to you. That’s for sure.

B2B 43 | Human Centric
Human Centric: If you can treat go-to-market as a true revenue organization where marketing, sales, CX, and everyone is involved throughout that entire buyer’s journey, it’s going to be a lot more successful.


One thing that caught my attention, which you forgot to mention and I’m eager to hear your thoughts on, is you did mention marketing, sales, and customer success, but you omitted product.

It’s interesting because the only company where product has rolled under the revenue organization was Clari. They rolled product under there as well. The first time that I saw it, I was like, “This makes a ton of sense because they’re playing a big piece into the revenue side of it.” Between Alyce and Airmeet, product was never part of the go-to-market strategy, which probably isn’t a great thing now that I’m thinking about it.

Being in MarTech and selling to marketers and things, it’s something where I understand the pain points because I’ve been looking to solve these for so long. It’s a little bit easier for me now. If you go into IT or some of these other industries, it may be a little bit harder. I think that I influence the product roadmap a ton because being a marketer, it’s things that I want to see. It’s interesting because I don’t see products rolling under GTM a ton, although they should now that I’m thinking of it. It’s weird. Clari was the only one that did that.

Let me be honest. I don’t expect a product organization to roll under a go-to-market umbrella. That’s super crazy to an extent because the product is all about innovation. You want to keep that separate from the actual go-to-market tactics. What I’m getting at is more around when you think about the go-to-market strategy. If you review on a weekly or monthly basis, product should be in those discussions.

A couple of weeks ago, I had Karen Steele, who was a CMO at Sendoso. She was talking about before the actual tactics or before the actual meeting, she sits down with the marketing and sales entire team. She initially has the leaders from product, marketing, revenue, and customer success. They talk about at a high level what’s working and what’s not. It’s not that they’re pinpointing or poking holes in someone’s metrics in that specific meeting. All that deep dive and roadblocks of what’s working and what’s not will happen at a subsequent meeting. There are ways to go about and do this.

I do agree. We do that a ton. It’s something where we have regular meetings with the product team that understands. It’s not like the product team is siloed, doing their own thing, creating the roadmap, creating features, and shipping stuff just because they think that’s what people want. At Airmeet, we had 100-person engineering and product teams. For a smaller company, we could ship a ton of new features and stuff. We talk to the marketing team on a regular basis. The product team was good about listening to customer calls and listening to prospect calls. Also, taking a lot of that feedback and implementing it back. It’s like a feedback loop to a certain degree, so that was definitely key too.

Switching gears a bit over here. Can you share for the benefit of our audience a recent go-to-market success story? I would you to share both a success story and a failure story. It’s up to you which one you want to pick and go with first.

I would probably say a success story first. Something that we believed in at Airmeet was this whole creator studio. Originally, when I joined the company, part of my role was to build out this creator studio. The vision for it was a collaboration with other creators because we agreed that collaboration between creators is a huge piece in a people-first go-to-market. I wanted to see if there was going to be anyone that would find value in that. Unfortunately, we’re not going to see it come to fruition, but there were so many people that submitted a video submission of something they wanted to create and collaborate with other creators.

We weren’t even giving them a ton of things. We were just giving them access to our design and our brand team, and helping them out when they maybe didn’t get there. Many people had creative ideas for things they wanted to create. We were going to use that and we did start to use that as fuel to the top-of-funnel aspect within our go-to-market strategy because we’re borrowing trust and authority from a lot of these creators. It’s like influence marketing to a certain degree, except instead of the brand telling the influencer what to do, why not collaborate with a bunch of creators?

I would always use the analogy of you go to an art studio and you paint, but when you go to the art studio, there’s a bunch of other artists there. What if all those artists want to create a painting together because you’re in one spot? That’s what I was trying to create. The early results that we saw from it were very successful. If we ran it for the rest of the year, I’m sure we probably would’ve seen even bigger results. For running it for six months, I definitely saw very good early results that impacted our revenue. It’s good to see there.

The negative side from the GTM side of it is my last role at Alyce. One of the things we were trying to fix was outbound is broken. How do you leverage gifting and direct mail in an outbound strategy so it doesn’t suck at the end of the day? We had a good vision of how to fix outbound to make it better, and how to make it not sound so spammy, which now that I’m thinking about it, that’s people-first. You were trying to put people first at the front of it. It goes back to everything. We want to put people at the center of everything that we do. The tactics that we were trying to deliver between sales and marketing, we didn’t want to call it ABM per se. We were calling it targeted marketing, but it was part of the larger GTM strategy side of it.

Put people at the center of everything that you do. Click To Tweet

We didn’t have the correct tactics in place throughout the buyer’s journey. We were driving a ton from the top of the funnel, but we were accelerating nothing. All of those opportunities were basically dying. We had the messaging, assets, and awareness. We just couldn’t accelerate those. I wish we did some things differently looking back, but it was still successful to a certain degree. I just think that it could have been so much more.

Hindsight is 20/20. You learned so much from that for sure. It all boils down to we need to get a campaign or a program up and running. It’s more of let’s experiment around a set of hypotheses, and see and test what works and what doesn’t. It has its own challenges and drawbacks. A good metric is if your experiment failure to success ratio is more like 30/70 or even 40/60. That’s a good place to be in versus trying to get a 100% success rate, but you’re just doing one experiment in six months or a year.

That’s the thing too though. Often, a lot of younger people in their careers are afraid of failing because they think they’re going to be blamed for something. Leaders within these organizations for years have always pointed the finger at someone if something didn’t go right or a campaign failed. Think about how many campaigns failed before you have a successful one. People don’t talk about failures. I love talking about failures. Think about LinkedIn. Everyone talks about, “I’m driving millions of dollars and all this good stuff.” What about all the failures it took you to get there? You have to be willing to fail fast and accept those failures, but what are the lessons learned that you can take forward to do something with?

Think about how many campaigns failed before you have a successful one. Click To Tweet

I completely agree. That is a very critical point that you mentioned, which spoke especially of those who are just in the early phase of their careers, their efforts, and failures. It’s upon the leadership team and the leader to encourage failures and do the shielding with the peers. That’s totally valid and relevant there. Let’s switch gears. I know you talked a lot about event-led, community-led, and partner-led. There are so many of these variations and variants around go-to-market. What are those 1 or 2 things that are keeping you on your toes or getting you excited? You did mention people-first. Do you want to expand and expound on that?

Going back to the people-first, it’s three big things because I feel like a lot of those other pieces fall under this. It’s create-demand, capture-demand, and convert-demand. Many people talk about create-demand and capture-demand, but how do you convert that demand? You have your channels, your metrics, and your offers below that. The overarching theme is partner-led growth, which fuels this whole ecosystem thing around it. When you think about channels for create-demand, it’s all about community-led growth. Community-led growth will drive to member-led growth, which is under the capture-demand. You have the community aspect. You then have these members or the audience that you’re looking to capture.

You could even use this for a podcast. Ultimately, you’re going to convert that demand into customer-led growth, customers, renewals, and advocates. There are metrics for create-demand and capture-demand. For create-demand, it’s all about your followers, engagements, and leads. For capturing member-led growth specifically, it’s about members, SQLs, and opportunities. When I think about the offers for those three pillars, content-led growth is fueling community-led growth, which is fueling create-demand.

You have event-led growth, which is putting the attendee at the center of everything. It’s through experience, engagement, and data. Those are the three things that make up event-led growth. That focuses on the capture-demand. You then have product-led growth, which is on the convert-demand. Ultimately, you still need a product that people love and want to use once you convert them. I think of it this way. The partner-led growth and ecosystem fuel the entire thing across all three pillars.

Something that I’ve done over the last couple of years is I’ve been studying CMOs, especially those who are what I call the winning CMOs. Take the analogy of the NBA, the league. There are about 30 basketball teams, but there is something magical about the top 1, 2, or 3 teams that they are consistent versus the remainder of 25 or 26 teams. From that viewpoint, I started studying. There are so many of these CMOs, but there’s something magical that the winning CMOs do that sets them apart.

During my study, it boiled down to three things that they do well. One is around content. They create unique and engaging content that resonates. An example that you and I know is what Gong has been doing so far. The second is around the community, so what Sangram has been doing and many others. It boiled down to Sangram’s mantra, “Without a community, you are a commodity.” Third is what I would call experiences/events. If you mix these three and if you do it right, not necessary that you have the resources and the budget to pull all of them and execute all of them at the same time. If you sequence it right, that’s your magical mantra or that’s what all the winning CMOs do.

I agree with all three of those. One thing is none of those three can be seen as an afterthought. Many people think of events or communities as an afterthought, but they don’t tie it into the entire GTM side of it, which you have to do to be successful. It can’t be its own individual thing with a team running it. How does that play across all the other functions as well?

What are the biggest areas or what are the things that you’re curious about, and what resources do you lean on? You did mention people, podcasts, books, and the community. What are those 1 or 2 things that you’re curious about? Who do you lean on or what do you lean on?

The biggest thing for me and I’m super curious about how this is going to play out is the creator economy in B2B and how that’s going to impact how companies operate their go-to-market models. I’m writing a book on this right now. The whole thing of influencer marketing. Part of the survey that I’ve been doing is 88% of brands are at least willing to try influencer marketing in 2023. That’s a pretty high number of companies willing to at least test it or say they’re going to test it once or have done it. I think that’s heavy in the MarTech and sales tech space. Once you get out of those two, it’s probably a little bit less maybe outside of IT.

I’m curious about where that is going to be. I think we’re very much in the early adopter phase on this whole creator economy and creator-led growth. How do evangelists that our employees play into a brand long term? That’s the biggest thing that I’ve been wondering about lately. What I’ve been writing a lot of my content, going back to the people-first, plays a piece of that. Creators and influencers in B2B, taking from that modern marketing playbook, are going to be so impactful if done right. It can’t be the brand telling the creator or the influencer what to do. It has to be very much integrated into your go-to-market strategy.

B2B 43 | Human Centric
Human Centric: Creators and influencers in B2B, taking from that modern marketing playbook, are going to be so impactful if done right.


I’ve been following certain people, big creators, small creators, and people that are talking about the creator economy. For the last 4 or 5 months, that has been my big thing. I’ve been listening to some podcasts. I have some community sides of it, and then the whole event. I’m hosting an event in Costa Rica in the first week of November. It’s the first-ever creator’s retreat. I’m getting twenty creators together. We have Airbnbs right on the water in Costa Rica. For four days, we’re holding workshops on how to be a better creator and how to come out and learn new things.

For example, we’re going to have experts that talk about YouTube shorts or Instagram reels. People that have been doing this well that maybe other creators in B2B aren’t doing right now, but they want to. Those types of things and those types of micro-events and experiences are one where I’m learning a ton but two, where I’m doubling down on.

Costa Rica is a fun place to be in. Which place in Costa Rica?

Playa Hermosa. It’s where Surf & Sales, Scott Leese does it. That’s where we found the spot. They do it right down the beach from where we were doing it. We have someone that’s been helping me with this. She flew out there and did a bunch of scouting for it and found these three Airbnbs right next to each other on the beach. We were selling tickets for it. I was like, “Is anyone going to buy a ticket?” We sold all the tickets except two so far. All I did was make one LinkedIn post. People are like, “I’m willing.”

I don’t know what is considered expensive or cheap, but it’s $3,000 to go and everything is included outside of your flight. For a learning experience, especially if you can expense it back to your company, it’s a pretty reasonable cost for being able to learn. We have some CMOs coming. We have some solopreneurs coming. We have some people that have been doing this well. I’m excited to learn a ton.

I’m a big believer in the influencer economy and the role of influencers. They clearly play a role in the B2C world. One name that comes to my mind is Jay Shetty. I don’t know if you’ve heard of this guy. Jay Shetty is big in the whole spiritual and personal development space. He was hired by our partner. He’s partnering with Calm and even Noom around mentioning them or having a personalized ad run in his podcast, and giving special promos for people who subscribe to Calm or Noom. That’s clearly working, It’s about how you bring that playbook to the B2B world.

It’s easier than you think because you can do a lot of those same things. I feel like on TikTok and Instagram, you see a lot of those B2C ads that are typical, but on LinkedIn, you are seeing more creators starting to talk about specific companies. Not so much products per se, but more companies. There was one that I saw. There were a bunch of people that posted about it. I think it was called Win.ai. They’re trying to not be the typing CRM, but it stuck with me because so many people created videos around it. They sent them a box and they opened the box on video. I was like, “That’s super smart.”

You have all these people. Think about how many impressions, engagements, and clicks you’re getting on that. Think about how much you would be spending if you were going to run paid ads for a specific campaign like that. You’re going to probably be saving a lot more money paying creators and influencers than you are running extra paid ads or something.

I’m eager to see how all of these play out and all the learnings that can come out from your event because there are so many topics. For example, how do B2B brands pick influencers and creators? How do they create that filter? That’s one. Next is how they structure the agreement. Is it term-based, incentive-based, or some metrics that they need to hit? It’s going to be almost like a sales OTE. You have a fixed versus a variable comp. There are so many of these moving pieces. You get to see all the things that are coming out.

That’s why I created my newsletter. The Creator Circle is all about the creator economy and influencer marketing. It comes out twice a month. I’ve worked as an influencer on certain campaigns with brands, and I’ve also paid influencers and creators as the brand. I’ve seen it from both sides and I’ve structured contracts. I’ve signed contracts. I have a few brand deals that I’m working with companies right now on specifically. In a lot of cases, what happens is they’re giving you a referral fee on close one deals that you both source and influence on top of what they’re either paying you for sponsored content, maybe a retainer per month, equity, or whatever.

When I was in my full-time role in my previous job, which was running product-led growth and product marketing, inner marketing at series-B company. One of the things that I was exploring with the founder and CEO was how we collaborate with influencers and help them to get more leads and more awareness for our brand, both for free trials or even a demo. We used to track that in Tech Stack or it used to be called. Now, it is called Partner Stack. That’s how we were tracking. I’m eager to see how all of these things play out. I sure will subscribe to your newsletter. I’m eager to see where this is going.

I appreciate that.

If you could look back at your career, who were the 1, 2, or 3 people that shaped, influenced, or mentored you in your career?

I’ve thought about this a lot. I don’t know if there are people per se. I do have one. His name is Pete Lorenco. I met him through Pavilion years ago. It was when they were running a mentorship program. I didn’t have a mentor. No one told me that I needed a mentor in my life. I always was doing my own thing. It turned out we had so many of the same interests. We had young kids. We both enjoyed sports and all these other things. We hit it off. He was helping me. He was VP of marketing at a publicly traded company at 34 years old. He has a really strong background.

He was giving me so many insights and helped me. I convinced him to come over and work at Alyce. He ultimately leads all of marketing at Alyce. He’s now VP of Global Demand over at a company called HYCU. I talk to him every single day. He played a huge part in helping me with a lot of different things, both personally and professionally. He’s a huge piece of it.

I think there have been not people per se, but LinkedIn has been huge for me. Just scrolling through content and seeing all these other people that have been sharing their advice and sharing their feedback. The best content that I love is when people share actual programs that they’re working on. What are the successes? What are the failures? What does it look like? Those types of people, whether it’s a one-time thing or I see it every single day, are hugely influential as well.

I completely agree, especially on the second part that you mentioned. Same here, I learn a ton from being on LinkedIn. The only thing that I have to watch out for and do is I should not be spending too much time on LinkedIn because there are tons of content, a lot of influencers, and good folks putting good cutting-edge content. To your point, I totally agree. LinkedIn is a great place for people especially those who are looking to up their game, go-to-market, marketing, and even sales for that matter. The final question for you is if you were to turn back the clock and if you were to go back to day one of your go-to-market journey, what advice would you give to your younger self?

Being a marketer, day one should always have to be revenue focused. You could be revenue-focused or you could be customer-focused. You have to tie yourself as a marketer to a revenue number. If say you’re on the customer marketing side, maybe it’s NRR, we all know it costs less to retain a customer than go out and acquire a new one, especially in today’s economy. Tie yourself to revenue as quickly as possible and figure out how you can make an impact there. When you’re impacting the bottom line to a go-to-market strategy and sales, CS, and the executive team see that as a marketer, regardless of the role that you play, you’re impacting revenue and this is how you’re doing it, you make yourself a lot more valuable.

As a marketer, or regardless of the role that you play, when you're impacting revenue, you make yourself a lot more valuable. Click To Tweet

Where can folks find you? I’m sure they can all find you on LinkedIn. Anything else that you want to mention here?

I would say LinkedIn. I have a podcast as well, The Anonymous Marketer. Feel free to check that out and make sure to subscribe to the newsletter, The Creator Circle. You can find all these links on my LinkedIn profile at the top. It takes you to my link tree with a bunch of different stuff. Shoot me a DM if you have any questions. I’m happy to help in any way I can.

Thank you once again for a wonderful conversation and good luck for your future journey.

Thank you so much.


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B2B 39 | Go-To-Market CMO

B2B 39 | Go-To-Market CMO


The go-to-market is all about connecting with your customers to buy your product or service. Who better to facilitate this than a Chief Marketing Officer? In this episode, Vijay Damojipurapu sits down with James Kessingerto discuss the vital role of the CMO in the go-to-market. James is the CMO of Hushly. Prior to that, he has been charting the waters of his career in the field of marketing, customer success, partnerships, revenue ops, and sales. He takes us across his journey and imparts great insights into a CMO’s approach under this strategy. James shares how he has shaped the go-to-market at Hushly and how it has evolved since taking on the role. He also talks about some of the go-to-market successes and failures he has observed, especially among marketers. Full of helpful information from his rich experience, James gives a great show to help you bring your strategy to success. Tune in to not miss out!

Listen to the podcast here


A CMO’s Approach To A Go-To-Market Strategy With James Kessinger

I have with me James Kessinger who is the CMO of Hushly. He’s coming from a very varied and accomplished background. We will get into a lot of those details during the episode. Stay tuned.

Welcome, James.

Thank you. It’s great to be here.

I always start the show with the signature question. How do you define go-to-market?

It’s always a fun one. I look at all teams in the company working toward a common set of goals with measurements and ownership of who’s doing what, which is ultimately led by a CEO. That person owns the go-to-market. At the end of the day, we all support that go-to-market function. That’s how I define it. It’s everybody working toward that common set of goals and with measurements because you have to have measurements.

You are the only one on the show who said that go-to-market is “owned by the CEO. No one has ever told me that.

I can’t change a sales comp. If you want to enter a new market or a new country, the CEO has to make decisions.

Both you and I and many others subscribe to what Sangram Vajre and his team and others are prescribing, which is go-to-market is not owned by one person. It should be owned by the CEO who has the entire gambit across all the functions. You did call about the CEO owning the metrics and then driving or guiding each of the functions but if you doubleclick, let’s go to the next layer, how would you as a CMO approach the go-to-market motion?

Largely, it comes down to what are we trying to achieve because my role is broader than the CMO aspect. I have to look at all functions, whether that’s customer success, sales, or even our dev op stuff, not just marketing. They all play a role in terms of what we’re trying to achieve and what we’re trying to do. Ultimately, once you’ve established this is what we’re trying to do, my job as a CMO, and probably most CMOs for that matter is to help orchestrate a lot of that to happen and making sure, “Is everybody pulling together? What do we have to do?”

Marketing touches everything from pre-sales all the way through post-sales and loyalty at the end of the day. That’s part of the go-to-market. You have to be able to touch the entire evolution of a customer and/or market on what you’re trying to do. That for me is understanding what we’re trying to achieve and who we need to rally together to get that because in the beginning, you may have to have a smaller set of folks and then broadly, you expand that out over time.

That’s all very internally focused. Let’s say you and the team are going after a specific market. How do you define the ICP? How do you do the research and the assumptions around your go-to-market?

We had to do this late last year because we were entering a brand new market that we had. We need data. Without that, you’re flying a little blind. You need to understand why are you making the decisions you’re going to make. For us, it came down to the data. I look at it as we had a set of customers that are more profitable than others but also, they’re using more of our products. The time to close is a little different and a little shorter. Ultimately, we have bigger relationships there.

For us, that was one of the reasons why we chose to nail down the cybersecurity path. We were heavy in technology as a company in terms of our market but when I look at it, let’s focus on this vertical specifically, which is cybersecurity. Is our ICP correct within this? Broadly, it’s correct for what we’re trying to do in tech but let’s make sure it’s correct here too.

That for me is where the data comes in. My job is to help look at how our past business has been looking from a close-one perspective. What do the deal sizes look like? How long does it take to close things? What are we losing? How much of the product are they using? It’s the consumption aspect of it. How many people do they have in the product? Can you start to define that ICP a bit more and then nail it? Ultimately, from there goes everything else. You have to get the messaging and your content ready. You have to start building things around that once you make a decision to go there but the data drives it, “Are you going in the right direction first? What direction should you be going?” That’s what we did.

The data really drives you in the right direction. Click To Tweet

I’m sure we will double-click on several of the aspects over there. Let’s rewind a bit over here. Why don’t you walk us through your career path? You’ve got a very interesting career path. I‘ll double-click on several of the things but I want you to tell your story and how you became the CMO.

I’m the COO and CMO. It’s a bit of a dual role. I’ve been in Hushly for five years. I started as the CMO and moved into a broader role that encompasses more additional responsibilities. Overall, I’m responsible for marketing, customer success, partnerships, revenue ops, and sales. My career path didn’t start there. I started working in enterprise companies that were in growth mode at their time, which is pretty important to say because those companies today are either gone or in the twilight of their heyday if you want to call it that. I started at MCI Telecom.

Its heyday. It was outmaneuvering AT&Ts and Baby Bells way back then. I stayed there for four years. I went into Cisco which at the time in 1999 was a leader in networking and expanding out of their core customer base, which was enterprise, and moving into service providers. It was a new market with new buyers. They were expanding all their products and service business.

Ultimately, I spent fourteen years there. I spent quite a bit of time and did everything from services marketing, partner marketing, and segment marketing, which is the SMBs for service providers. I carried a bag. I was in sales for a couple of years. After Cisco, I went into a smaller company for about a year, ran their channel sales and marketing, got recruited to work in VMware, and ran their American big partner organization for about three years.

That’s where I cut my teeth and built my career because you could do so much in these big companies. I left the big company life and went into my first startup called CloudVelox. We got acquired VMware a year later, which was crazy. Instead of staying in IT, I was using the product of the company that I’m at now, which is Hushly. Rather than rejoin VMware, I jumped into the MarTech industry and moved to Hushly.

I can talk to CISOs and CIOs. You have all the messaging. You can talk to folks but it was interesting to me to talk to marketers, market to marketers, and sell to marketers. It was fun. That was what drew me there more than anything else. I get to touch technology, be involved with it, and talk to marketers pretty much all day, whether that’s practitioners, directors, or all the way to the CMOs. That for me was a fun run here for the last few years here. That’s my story.

You mentioned MCI. Here’s a little bit of my background. I came from India. I was doing my Masters. Back in those days, we were all purchasing the MCI calling cards to call back home. It was crazy. After that, I was in the telecom industry at Fujitsu Network Communications and even Microsoft. We were selling to MCI.

We got bought by WorldCom. UUNET was the actual backbone of the internet way back when. That was it. WorldCom became Verizon.

It looks like we might have interacted, not directly but we were selling to the same customers when I was at Microsoft working on the Mediaroom IPTV platform. You were maybe involved at Cisco in the IPTV world. We did cross paths but not directly. Here we are, finally touching ways.

It’s a small world.

You also mentioned selling two marketers in your role at Hushly. It’s almost like you are dogfooding your product and trying to showcase or get folks on the marketing side to adopt your product. That’s a challenge. I experienced that personally when I was at SugarCRM. I was a product marketing director there. I had to use the CRM but at the same time, I was selling to marketers and salespeople around CRM.

We’re all skeptical. I’m probably the biggest skeptic out there for sure. Our inboxes are full of marketing. Honestly, I get SDRs and PDRs. In every agency, everyone is flooding your inbox, and then you got the normal sales reps calling you and trying to sell everything. We are very skeptical buyers if you want to call it that, which is good. The good news is I understand that. I come from a level of understanding. It is about having to prove what you’re doing, which is good.

We’ve got a good product. Without a good product, it’s hard to do any marketing honestly because you’re fighting against your product. If you don’t have a good product in the market, it makes it much more challenging than if you’ve got a product that people care about. You’ve got advocates out there, you can show an ROI, and you’ve got people using it and willing to pay for it. That makes your job that much easier because you can now start to showcase and tell different stories versus if you’re making up a story that’s maybe not true.

Without a good product, it's really hard to do any marketing. Click To Tweet

Your case is unique. Visual marketers get to that point. In your case, you were an avid user of Hushly. You loved the product and then moved over into Hushly, selling and getting others to adopt Hushly.

I was able to at least bang the drum before I got here. It was fun. It worked. The product worked for me, which is one of the selling points of why I came as well. It worked for me and I get it. These are problems that are in the industry. We were a single product back then. Now, we’re 9 or 10 products. It was unique. It solved a unique problem. It was a great story.

Let’s double-click on that. What does Hushly do? Who do you serve? Who are your customers? You mentioned marketing but let’s go into the use cases and the pain points that you solve.

For us, B2B companies or any industry is who we’re laser-focused on. It’s not a B2C. While it could be used there, we don’t go there. We’re heavy technology. We’re in cybersecurity. Our personas and the people that we sell to are digital marketers. They’re folks that care about SEO and SEM and paid marketers. Because we’re an experience and conversion platform, it comes down to the demand-gen marketer. You care about, “How do I activate my content? How do I educate buyers out there and get them to convert?” The demand-gen marketers are probably the main persona that we care about and sell to. Around that, it’s the content marketer. Content is the fuel for your engine.

If you think about the advent of the whole account-based marketing thing that has gone over the last few years, it’s field marketing. Field marketing and the ABM market are out there. They’re the ones that are at the pointy end of the spear because now you’ve got technologies like ours, 6sense, Demandbase, and the other guys. You’ve got the ability now to drive not just one-to-one models but one-to-one in a scalable fashion in terms of being able to use unique page ad things, different ad structures, all of the outbound sequences, and everything else.

It has made that marketer a little more efficient, and since that role has gotten bigger, the ABM marketers have. You have a little bit of that blended demand-gen and ABM marketer that we try to pull together because they’re critical for us. I see that one, and we have people buy our APM side of the platform. We get introduced to demand-gen marketers later.

That has been an interesting one. That’s the main one out there. The ones that are still there because I’m a big partner marketing guy are their partner marketers. There’s a lot of indirect stuff that goes on. They have these big MDF budgets. Is the vendor out there? How do I get partners to activate these partners on digital campaigns and be able to use our technology but at the same time, use our content and things and help them market better their services and their uniqueness?

Part of what at least I’ve been helping some of the partner marketing teams now do is leverage our technology and use it across however many vendors they want. The idea is to try to now tell a story but be scalable with what you’re doing, even if it’s making your Salesforce lounge. You’ve got another lounge over here at Cisco or whatever is in your quiver as a partner out there. You should be able to have different stories for different things, capture your leads as they come in, and understand those leads are attached to accounts.

B2B 39 | Go-To-Market CMO
Go-To-Market CMO: You should be able to have different stories for different things and capture your leads as they come in.


I’ve been studying CMOs and something that sets up other CMOs and go-to-market executives in general is it typically revolves around three pillars, which is content, which you mentioned earlier. Build a winning go-to-market. It’s typically around content. You have a community, and then it’s experiences/events. These are the three typical playbooks that I’ve seen. There are more. I‘m curious. How have you shaped the go-to-market at Hushly? How has that evolved over time?

There are two things. As with any small company, it’s sales-led first directly. Unless you get out of the gate with a partner model, it’s sales-led. Now, with the advent of a lot of this product-led growth stuff where I can come on and turn on a product for somebody and let them try it, and then they hit their maximum pretty quick, “If you want more features turned on, give us money.” We started with sales-led growth. We have moved into some partner-led activities.

The community stuff is something that we’re part of but we’re not probably driving a large community. As we continue to go, I’m looking at where can I put my foot and my stamp on various other communities that help drive relevance for us because communities take a long time. You have to have somebody dedicated to that who can drive conversations, stimulate the community, and build the community for that matter. That’s a different lift.

PLG is a whole different motion. Your products, your back end, and everything have to be set up. Your sales model is different. Your marketing motions are different. Whenever you take any one of these go-to-markets, you have to be prepared for it and thought through. You have to think through what you’re going to do. We looked at PLG. We’ve got a couple of products we could probably turn into that but we need to make some fundamental changes in the product to do that.

B2B 39 | Go-To-Market CMO
Go-To-Market CMO: Whenever you take any one of these go-to markets, you’ve got to be prepared for it and think through what you’re going to do.


Before, we were like, “We’re PLG.” Let’s fix these things and make sure that we’re ready to be one-touch because you don’t want to have a bad experience. The bad experience is going to screw you up. Once those things are done, then the rest of it you pull together, which is like, “The product is ready. Are the rest of the pieces of the puzzle ready to go with you?”

Especially the last piece that you mentioned around PLG takes me back to my time when I was hired at GoSite to lead their PLG effort. One of the things that we did was we said, “We are all in on PLG.” That was about 12 to 18 months prior to my joining. It’s hard to let go of your existing go-to-market motion that’s working. There are a couple of things. You want to target or move upmarket from micro. In our case, it was micro businesses like one owner to quantify employees and then move to 20 to 50 employees and above. We were selling primarily through inside sales.

That was still happening but at the same time, we wanted to go and move everything to PLG but there are bigger questions that we need to answer. First of all, are the buyers and the users that we are targeting comfortable trying the product on their own? Will they make the jump to move and purchase? Even prior to that, are there onboarding hurdles? Those are the challenges that we ran into.

Those are legitimate. Think about it. It’s the person in the company. If you say, “We’re SMB. We want to move to the enterprise,” that’s still a pretty big lift. You need a different Salesforce. You get a different comp structure. You need different marketing. Is your product ready? Is it enterprise-class? Here’s a short story on this one. In Cisco, we were going reverse. We were enterprise and certified. We started up this small business group. Think about it that way. It’s a purpose-built product and everything.

You can’t go down to the SMB and have an enterprise-lite product. You have to talk to the SMB. Small doesn’t mean stupid. We did all these focus groups. Small doesn’t mean we’re dumb. We’re businesspeople. We run a business. We don’t need an enterprise-lite product. We need an SMB product. It needs to fit what we’re trying to do. We did purpose-built products.

You have to do the work, whether that’s going up or you’re coming down, or whether you’re trying to do a completely different motion like the PLG versus a sales motion. You have to think through it. There’s a lot of big lifting that has to happen when you make one of those changes. The people that started a PLG product that want to go on sale are in the same boat. They have to now figure out, “What kind of salesperson would sell this thing?” It’s not going to be that you’re selling the PLG because you got that. What are you selling if you’re trying to sell it at the enterprise? Is it a seeding strategy? Do you need the seeding strategy wrap? You have to go through it.

We can go on different go-to-market mistakes but we’re not going to cover them in this episode for sure. Taking a step back more on the lighter side, how do your folks and your family describe what you do for work?

I have five little kids. I would say, “He talks on Zoom or Skype, sits on his computer all day, types on a keyboard, and makes some interesting pictures, graphics, and slides.” That would be pretty much the extent of “That’s what dad does. Dad says he’s in marketing but I don’t know.” It’s hard. I have elementary school kids. They’re not going to grasp what I’m doing, whether I like it or not.

Let’s get into the next section, which is around go-to-market successes and go-to-market failures. It’s a segment that the audiences love to dig into. As you and I know, go-to-market involves more often than not more failures than success stories. I‘ll leave it to you whether you want a success story or a failure story but we should cover both for sure.

We covered the success one a little bit earlier. It’s probably worth saying. At least I’m proud of it. The idea is to get alignment across all parts of the company and go after cybersecurity. It was nice to make a decision because it started with the data. It wasn’t a bunch of conjectures or somebody saying, “We have to go this way because we think it looks great.” You look at the data.

That for me was the big piece but before we were able to make that decision and before we had the data, I knew we were trying to do it. It was also about operational excellence. We had to get our operations in order because with startups, you can build and keep running, and you got a lot going, but if you don’t take the time to also connect a lot of the dots in your infrastructure, you have bigger headaches as you get bigger. I’ve seen that as well. As you get big, you got human middleware being thrown in there.

For me, the big piece was getting operationally efficient, meaning getting HubSpot working properly and understanding the data flows because we use it for CRM, not just the map. We’re using it for both mapping our product in there and what we’re doing with all the analytics platform stuff. Everything that we’re doing is pumping all that data in and understanding that 360 of the customer, where they began, where they ended, what they start using, how long it takes to onboard, and all that stuff.

Taking all those things into account was a success for us, and then being able to use that data, make a decision, ultimately move into that market, and full force head in there. I was in there a little earlier in November or December, but as a company, I was trying to seed. I’m doing more of a seeding strategy but then in January, we pulled budgets around there. We got things worked out on sales and CS.

Everyone is singing the same song sheet and driving through there. That for me was probably a good success. We’re seeing success. That is a good one to start with. When you think about go-to-market failures, God knows I got them from way back everywhere. It’s always interesting. I heard this from a leader way back, “Feedback is the breakfast of champions.” Whether you win or lose, you have to keep trying stuff, but making a decision that isn’t grounded in enough data is always a failure that marketing has to be aware of.

You can make decisions in sales, “This thing is going to probably come in. We know it’s coming in. We’ve got it as upside rather.” There’s enough data out there to understand that you only have about ten conversations that have happened. It takes twenty to be able to close a conversation. You’re not going to close this thing this quarter. You’re not near it. A lot of the predictive stuff is getting fine-tuned out there but marketing has always had that.

For us as marketers out there, your failure is going to start usually at the data. If you cut something too short, that’s a risk as well because if you cut it short, then not having enough runway and enough data to say whether something was a success or failure, that’s as bad because you’ve altered the outcome, “We’re going to run this for a quarter. This thing was terrible.”

As marketers out there, your failure is usually going to start with the data. Click To Tweet

The reality is if you know your sales cycle is 6 months or 9 nine months, and you’re running campaigns, messaging, and stuff, it takes a while for some of these things to catch up. You have to understand you’re taking people on a journey with your content and your sales team. Everything is stitched together. You have to give them time to play out. What too many executives do, whether that’s CEOs, COOs, and even CROs because sales is guilty of this as well, is “This thing is not working. We have to get out of here.” it’s like, “It’s actually working. What we’re seeing is incremental successes come through.”

Ultimately, what you start to see down the road is you’ve got a close-one business and better engagement. You’re getting more at-bats. That’s where I’ve seen stuff for me in the past. I’ve cut it off too early and I make a conscious effort now to say, “This is going to run for this long. I want to see these milestones hit right in terms of some incremental successes along the way.” You have to be able to see some things because you have to tweak them.

Marketers always need to be trying things but also tweaking things. Ultimately, you’re trying to tweak it to make sure that it’s not just “We leave it out there. Hopefully, it works. It didn’t work.” You need to be working with it the whole way and understanding the ebbs and flows. Like ABM, you have to have weekly cadences with sales. You have to understand, “These things aren’t working. These 20 accounts are engaged while these 40 are not. Why are these guys engaged?”

It’s about digging into the details and the data, understanding and working the problems that you see, and ultimately trying to make these things successful. That for me is the big number. The biggest failure I see is not letting things run long enough and not using data to make decisions. Sometimes you have to buck the system, especially as a CMO. It’s a hard position to be in because you have to be able to tell the CRO. If you’re reporting to a CEO or COO, you have to tell them, “We’re going to lean into this a little further.” You have to make the call.

B2B 39 | Go-To-Market CMO
Go-To-Market CMO: The biggest failure is not letting things run long enough and not using data to make decisions.


A lot of the time, you need to have a seat at the table. They have to respect you. Respect is earned and all that good stuff. At the end of the day, you’re there for a reason. You’re there because you know your job. You’re not the CRO doing the CRO’s job and predicting and forecasting. That’s not what you’re doing. You’re doing marketing and helping them tell the story, get the at-bats, and sell to accelerate. That’s where you need to be. You need to be able to own that and the market transitions, “We see a market transition happening. We need to be able to capture that.”

You covered a lot of important points when you were mentioning the success but more importantly when you’re talking about the failure. The key lesson that at least stood out for me was, first of all, not letting something run long enough. Typically, in go-to-market engines and teams, I’ve seen people try something for a couple of weeks or a month and then pivot.

It’s terrible. You can’t do that. If you’re going to do something that short, then don’t do it, honestly.

That’s one. The second one you talked about is around data or using data to make a decision either to pull the plug or to show that we are making incremental progress and then you continue that. Can you share a specific example? You did mention one around ICPs. Is there anything else that comes to mind either from VMware or Cisco?

We were doing a program. We built part of the marketing concierge. I was using an external agency to see “How do you help these smaller long-tail partners out there?” You have your top 100 if you want to call it that. They don’t usually need a lot. You give them some money, and you can approve their plans but then how do I help serve a lot of these long tails?

What we used was a concierge program. The concierge was like, “Think about the fractional CMO world of a fractional CFO. I have a marketing person that’s here to help you plan and execute marketing campaigns on your behalf.” For most of the smaller partners out there, it may be a team of one. Sometimes it’s a salesperson dumping as a marketing person.

It was a great success but you’re not going to see that right away because they’re in the same sales cycles as your company. What we’re able to start to show was that over time, they’re inbound because it’s now about the partner. The inbound leads for them were going up. Their meetings and at-bats were starting to go up. Their deal regs were going up. You saw that over the course of two quarters.

What you started to see were incremental things happening in Q1. A lot of things had to happen but when I started to do the measurements, it was like, “Let’s look at six months, and then we can reverse. Do we see any little things happening?” There are some green shoots here and there but broadly, what you started to see was that happening over the course of the year. We were able to do $400 million in the pipeline, which is pretty huge. I had a whole slide on the thing. We were able to do $80 million a quarter in a net new pipeline and activate partners that were selling either nothing or next to nothing for us.

This was for them a big boom because now they’re getting business from us and a little bit of money, which was a marketing concierge. How do we help them do that? For us, it was great because in the aggregate, looking at more of the program or the application of stuff. For individual partners, some did well, some didn’t, some did okay, and some didn’t do great. At that point, it’s like an ABM strategy.

You’re going to cull the herd a little bit, “These ones are doing good. Let’s put more in. Maybe we move them to a different model.” You begin to evolve but that for me was pure go-to-market play which was, “We need to do something not just for the 80/20 rule, probably 90/10,” 10% of your partners are probably driving 80% of your business, “How do I activate even the next level down because I can get these guys going for multibillion-dollar companies?” That can be a big jump. That’s important. When you get advocates, they’re going to get more certifications. They want to start selling your stuff.

One other thing that you touched upon earlier is we need to convince the CEO, the CRO, and others around, “We need to extend this initiative, campaign, or program a bit more even though we‘re not seeing.” That’s one area I have personally struggled with in my previous role. A COO and even the CEO asked me, “I‘m not seeing any leading indicators moving on this. Is this going to work for us or not on this specific paid digital as an example on LinkedIn or Facebook?”

There were some points where I said, “The data is showing otherwise,” but I had a tough time. It was a challenge for me personally, especially as someone like an INTJ who is very datadriven and thoughtdriven. I used to struggle to give a response. What is your advice? If a marketing leader is in that position, how would you frame that?

I can use my example in that one, especially ads because ads are very subjective but now, it has gotten a lot better. When I look at ads, let’s say LinkedIn. You can pretty much start to see early indications about what’s working or what’s not quickly. I’ve noticed that even with us. That’s where you’re not waiting a quarter to adjust your ad strategy for sure. That is a real-time endeavor that’s happening.

We’ve got five content pieces out there. We’re swapping them out every two and a half weeks with different ad structures and different-looking ads. Sometimes you’re re-skinning stuff every month but it’s because I’m seeing immediately when things are going up. They hit a plateau and then start to fall out. If I take that same ad and re-swizzle it with different content, a new call to action, and a different graphic, it can go right back up.

On those kinds of things, the leading indicator is, “How many downloads are we seeing? What are we seeing?” That’s an evolution. It’s the lead strategy. I’ve got leads coming in from various companies that are doing certain things. We’ve got them to dial this one thing from LinkedIn. We’re going to get them into a bit of a nurture flow. We want to get them back to our website and start consuming content.

That’s what we’re measuring, “How much consumption is happening? What personas do we see engaging with? Are these in our ICP?” All those come together, and then we start to see meeting requests coming through from these LinkedIn ads that were then on our side. You have to be able to start. That takes time. You turn on the garden hose. It has to go from the beginning all the way out toward spring. It’s the same thing with any of those strategies.

You have to have the ability to understand that you can affect some things upfront and tweak those things because if you don’t have ads that are working upfront, you’re going to know right away. You have to get your content right and your message right. You should start to see. Ultimately, the later stages are where you start to see, “The consumption is happening. The downloads are happening.” You start to see the demo request or the meeting starting to happen.

Those are long plays. That’s SEO. You have to get your domain authority. That’s a long putt. SEO is a year because you have to build it over time. You have to understand, “Are you going after your keywords and your long-tail keywords? You need a lot of content. You need to start getting rocking.” It takes time to build that up. That’s where the ad strategy can help you short-circuit some of that but it still takes time to get that earned media versus everything else.

Once those two strategies are together, your ads are probably going to be at the end of the day driving the majority of your inbounds and that stuff but over time, you will see that the other SEO that earned media is starting to drive as much if not more, helping your ads for that matter, giving you a little more lift than what you’re doing, and even reducing your cost of it as well. Those are where I see the big ones.

That’s a great explanation of that. You can attribute and measure the performance of many of the channels, especially digital. You can see the feedback loop coming in 1 to 2 weeks and know if it’s working or not. SEO will take time, six months at least, if it’s working or not but then there are other channels like a community or a podcast. You may not be able to show attribution right away.

It’s people doing the big awareness campaigns. The more you can push things out there about your brand and who you are, you’ve got a good community. You’re nurturing this community out there. Those are all seeds. You’re sprinkling seed in the ground at the end of the day because you’re trying to show thought leadership. You’re trying to show you’re different. You’re trying to get advocates out there.

B2B 39 | Go-To-Market CMO
Go-To-Market CMO: The more you can push things out there about your brand and about who you are, the more seeds you are sprinkling in the ground to nurture your community.


Even if you’re not flogging everybody in the community about who you are, you’re stimulating conversations about B2B in this case. You’re having a B2B broad go-to-market conversation out there. It’s not like you’re trying to hammer somebody over the head with, “You have to buy this.” All those are seeds out there. Communities are good for that. You get people that naturally will be like, “What is this person all about? That was an interesting podcast. I should look at what they’re doing as well.”

The community stuff and a lot of the things that you see out there are all strategies that help earn your brand. There’s a lot of work that has to happen on the brand, especially for small companies. When I was at a big company, I was always a steward of the brand. What you don’t want to do is you’re the guy that ended up getting on CNN or CNBC, “Sorry about this,” and walks into the back.

You’re a steward of that brand. You didn’t build that brand. That brand was built long before you got there. You’re now having to take that brand and keep pumping it up. At the end of the day, they built that over time with you hopefully on the bus. In the startup world where I’m at, you have to build the brand. You’re building demand, and you have to capture the demand at the same time. It’s a different deal.

You have a varied skillset working at large companies, keeping up the brand, driving demand, and working with the different partners, go-to-market channels, and then the younger startups or the smaller companies. You have a breadth of experience, skillsets, and strengths. Coming back to strengths, what would you call out as 1, 2, or 3 strengths of yours when it comes to go-to-market? What do people reach out to you for?

I would start with this. Problem-solving would be the first one. I can typically look at any situation, quickly diagnose the problem, and place several scenarios in my head with multiple solutions. I tease out ways to have better outcomes. I’m a logical thinker. I use data but I also use experience to help guide my thinking because God knows I’ve made plenty of mistakes. That to me is one of the areas that I know people come to me for. The other one is I get things done. Let’s make sure we get it done because you can’t pontificate forever. You can’t have analysis paralysis. You have to be like, “We have to get them.”

I like to jump in, do the work, and then bring others along so that everyone can see the vision and the outcome but you have to be able to start some things. The big executive companies always have these huge edicts out there, “Do this.” You have to take these edicts. It’s like a CEO, “We’re going to go here. We have to figure that.” You have to go, “Here’s how we need to get here.” You should be able to diagnose problems but get something done. There’s enough time to analyze and do things.

That’s one of the things I probably have excelled at from being in big companies and watching these things. Now, at a small company where you have to not just have your edict out there, I’ve also learned to start doing that, and then bring everyone with me, “Do you see where I’m trying to go? Do you see the vision?” You’re leading the charge on that as well.

That for me has been a big one because what you’re able to do when you bring people along is you’re able to have that output more refined because it’s not just you. You’ve got more people helping you refine things. They’ve got the unique experience they bring to the table. In the end, you’re showing results and you’re able to get things done. If you’re only doing a strategy without any execution, it’s like having a theory that you can’t operationalize. Those are the two. It’s problem-solving and I like to get things done.

That’s pretty cool, especially the second point that you mentioned about getting things done. I can’t recall the exact name. I don’t know if it’s Frank Slootman or a couple of others who mentioned strategy. When you boil it down, it’s all about execution. Execution helps you build your strategy, not the other way around.

Every strategy fails at execution. That’s what it is. If you can’t execute, then the whole thing is dead.

Every strategy fails at execution. If you can't execute, then the whole thing's dead. Click To Tweet

Switching gears, we are coming up on the last couple of segments. I know you need to do other things over here. Who do you lean on? What resources do you lean on like people, mentors, communities, or podcasts? How do you keep up to date on not just go-to-market but even clearing your mind and being fresh all the time?

Honestly, I talk a lot. I talk to real people, whether that’s our customers or other marketers, and listen. A lot of times, you have to listen to what’s going on. I’m in these communities. I’m in a bunch of different ones. I like to be a bit more of a fly on the wall. When you’re coming from a MarTech company, you’re talking to marketers. I try not to interject too much because it looks like you’re selling but I like to understand the conversations that I’m seeing because I like to take things and boil them back up. Are they seeing bigger problems? What’s happening out there?

For me, it’s more listening and reading between the lines of the different conversations that I have. That’s how I stay up to date because I understand the things I’m seeing, where customers are saying it’s going, or general people like, “We’re using this. We’re doing that. Have you seen these things?” Those are interesting to me. Communities help because they curate different types of conversations.

Sometimes people are more comfortable in a smaller community or a little group. You will get more real unvarnished opinions if you’re chit-chatting with somebody. That to me is the big one out there. Staying active in those communities and having those conversations is the best way. I read some books here and there but I’m a book on tape versus reading because I read a lot of stuff on email every day. I try to save my eyes. Honestly, those are my main outlets.

If you were to look back at your career, who were the 1, 2, or 3 people who played a role model, a sponsor, or a mentor that moved your career and created certain inflection points?

There are three. I’ll preface this. Two of them are from Cisco because I spent so much time there. The first one would be a gentleman by the name of Mike Farabelli. He was our VP of Services back then. He went on to Microsoft and became one of their GMs there. He had an awesome work ethic. He gave me room to try anything and fail. He also had some good feedback and some good mentoring honestly. He would be one. I haven’t talked to Mike in years.

Lauren Ventura would be my next one. She was a manager of mine. She hired me into Cisco. I worked for her twice at two different companies, believe it or not. She was a great manager and a great leader. She was there for me, even to this day. I’ve worked for her twice. She’s smart. She’s another one who gets things done. There’s something to be said for those kinds of people. She’s very analytical, thorough, and everything else. She was great to work with for that matter.

The last one I would probably say is my current CEO and co-founder. I’ve been here for five years. For me, building a company from an idea and then trying to nurture that idea into a business and continuously grow and evolve is truly amazing to see. It’s hard being on the ground floor, and I’ve been able to see that, and doing a bootstrap for that matter. We have even taken the money.

It’s even more of a challenge because you’re having to do things that are unnatural versus how you can spend willy-nilly out there. It has been interesting. He has been an interesting one. I’ve learned a lot probably more of a business lens by dealing with Jeff. That has been interesting for me. He’s one of the influences. He’s helped me grow from that pure business perspective.

I learned about the fact that Hushly is a bootstrap. Building a bootstrap business is a huge challenge. We talk about building tech startups, assessing and validating your problems, and then doing the productmarket fit. I’m trying to do a fundraising. That’s a whole different thing. I imagine the money that you need to run your business has to be generated by your business to grow. That’s another level of challenge.

You’re running it on invoicing. It’s failing at invoicing, and then you run out of business. That’s what it is. When people talk about efficient growth, this is efficient growth. It’s how you get efficient with what you’re doing. You apply that to any funded business. You need to get efficient. There are always ways to get more efficient but it’s a must-have for a bootstrap.

One final question for you is this. If you were to turn back the clock, what advice would you give to your younger self?

It’s probably not related to marketing. I would say, “Stay long your Tesla call options for ten months longer, and you’re not working again.” That would be it, honestly. I had some great call options out there but I digress.

I never expected that response. On that note, it has been a great conversation, James. There are a lot of insights, anecdotes, and lessons for our audiences. Thank you. Good luck to you and the team at Hushly.

You bet. Thanks.


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B2B 37 | Arbinger

B2B 37 | Arbinger


Marketing isn’t just about selling a product, it’s about understanding and shaping the mindset of those you serve. Whether they are consumers, retailers, or both. In this episode, Lisa Sharapata, the CMO at Arbinger, shares her incredible career journey from creative design to marketing. She dives into the unique challenges and opportunities of the B2B2C model and how Arbinger is reshaping marketing. Lisa also discusses the importance of performance management and shares other strategies for success that have helped her rise to the top. She also introduces the concept of the inward versus outward mindset and explains how it can transform both individuals and organizations. If you are looking to gain insights from an accomplished marketer with a unique perspective, then tune in now.

Listen to the podcast here


The Holistic Approach To Marketing: How Arbinger Is Changing Approaches To Marketing With Lisa Sharapata

In this episode, I have the pleasure of hosting Lisa Sharapata, who is the CMO at the Arbinger. Lisa and I have been crossing paths and spoken on and off over the last few months. I won’t get too much into the details and spoil the fun here for all of you readers. Welcome to the show, Lisa. I’m super excited to have you on the show.

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

The signature question I always ask my guests and I start the show with this one. This is what the readers love to hear as well from the guests, which is how do you define go-to-market?

It’s a hard thing to define. Also, I’m guessing every guest here said something a little bit differently and if I even asked everyone in my company how they define it, it would be different. For me, it is the holistic approach to how you are going to market. That includes what is your product, what’s your product offerings, how are you pricing and packaging, and positioning them to go to market. It’s your brand and your marketing strategy. What channels are you using? Is it inbound primarily, outbound, and those types of things? How are you looking at customer expansion? How are you looking at lifetime value? All of the different gadgets and things that we have control over for how we are approaching taking our product to market and making revenue.

In the common threads that I’ve seen and heard from the different guests, one thing that stands out is it all starts with the customer, the buyer, and the user persona whom you’re serving with your products and services. It always starts with that. After that, you need to work internally as well as with your partner ecosystem as you are serving your customer base and user base. That’s been a common thread and that’s what you referred to as well.

You also touched upon the different channels. That’s a big factor in the go-to-market, which is what are the different challenges inbound? Is it outbound? What type of motion? Is it product-led sales, product-led growth, sales-led, and so on? Something that you touched upon that not many of the guests have touched upon, Lisa, is it’s not up to the point where a person becomes a buyer or a team becomes a buyer or customer. A lot of heavy lifting happens after or once they become the customer. You also indicated the different metrics around that. I think that’s a very important point we should focus on. That’s a great start for sure. Why don’t you walk us through your career journey? A quick summary of what brought you to the point of where you are now and who you serve.

I started in graphic design and I love telling that story because I didn’t know anything that I know now when I came out of college. I was more focused on the creative aspects like branding. I worked for an agency and what I quickly learned about myself was I want to understand my audience. I want to understand the why behind what I’m creating. This side of things is very subjective. However, if I knew who I was serving with that piece at that moment or what the purpose of it was, it was so much easier for me to do something effective. To get those answers, I ended up becoming more of a strategic player in the marketing world by moving in-house.

I enjoy and prefer to be working for one company instead of a whole bunch of them so that I can be the driving force behind the why we’re doing what we’re doing and how we’re going to do it. Over time, I moved into B2B tech. I was in that space for over a decade. I’m now with a company called The Arbinger Institute, which is a leadership development and culture transformation. We will move into the tech space, but I’ll say for right now it is nice to be more focused on, “We’re trying to get that product market piece down and understand our audience and how we can best serve them before we grow into that new world.” It’s been a breath of fresh air.

Sometimes it’s better to work for one company instead of a bunch of them. It allows you to be the driving force behind why you’re doing what you’re doing and how you’re going to do it. Click To Tweet

I think you are one of the rarest people or the fewest people who have started their career in creative design and worked their way up the marketing chain, all the way up to a CMO. It’s very impressive and very inspiring. I’m looking at your LinkedIn profile. Earlier on, you started in the creative world. You are at Richmond American Homes. It has nothing to do with tech. You are in the retail space, which is Kohl’s and Jockey. You are at Encompass and you are the marketing director serving the retail world. Is that correct?

Yeah. It’s called the B2B2C model. It was very interesting because we were creating a product to sell to retailers, but we also had to help them sell through to the consumer. Again, I learned a ton about understanding my audience and it’s all applicable. It all comes down to the same things. People buy from who they like and trust and you got to create a great experience. It was helpful.

B2B 37 | Arbinger
Arbinger: The B2B2C model allows your product to sell to retailers as well as help them sell through to the consumer.


I’m curious. You made the jump from a creative design space to retail and then something happened. You moved to Teradata into the tech world. What were some of the key factors or was it by accident or by design? How did that happen?

The first company that I worked for outside of an agency was called eCollege. They were one of the first IPO tech companies back in the day. One of my old bosses from that company was at Teradata and she was like, “This would be the perfect place for you. You’d be such a good fit here. There’s so much you can do.” She sold me and she brought me in and the rest is history.

Since then, you’ve worked at big brands including 6sense. You’ve worked at Mindtickle and BoostUp.ai. It was a tech startup and then you also ventured and played the role of an advisor. You are currently an advisor with Hushly and now you’re a CMO at The Arbinger Institute. Switching gears here, you did mention at a very high level what you do with Arbinger. For the benefit of our readers and also to set some more context here, do a quick 30 seconds of what Arbinger does, who you serve, what are the different challenges, and how we are looking to reshape the marketing and go-to-market there.

Arbinger started many years ago and it’s based on this concept of mindset being the thing that is going to change outcomes. One of the things that have resonated with me is you can’t change behavior in a meaningful lasting way without changing your mindset first. Think about your New Year’s resolutions and statistics around how many of those behaviors don’t stick because, without a fundamental shift in your mindset, it’s hard to change your behavior. Over time this has become more of a focus on B2B, on corporations and how we help them to achieve their desired results through a change in mindset. The premise comes down to this concept that with an inward mindset, we’re treating people like objects that do not matter.

They’re objects. They are obstacles. They are things in our way basically of getting what we want. For an organization to achieve its results, everyone needs to be collectively working together. If everyone has their own agenda, you will not get the collective group as a whole to achieve those results. You run into silos. You’re going to run into people. Some people will shut down. They’ll quit and resign. You’ve got other people who you are going to have no situational awareness of and be pushing other people who then are not as engaged.

You’ll run into all these different problems when you have that kind of mindset. We’re focusing on leadership development and helping create leaders who can see others as people whose objectives and needs matter as much as theirs do. When you look at things from that perspective and you’re all in it together working towards a common goal and objective, you are four times more likely to achieve those results.

It’s our primary focus. We also have a solution called Performance Management which is more on the performance side of things. One of the things we say is don’t hold people accountable but create accountable people. If I’m sitting over your micromanaging telling you what to do when I walk away, are you going to keep doing it? You want to create a culture of people who are accountable to the bigger goals who want to do what they should be doing.

The third piece is outward inclusion. It’s a DEI product offering, but it’s focused again on inclusion and belonging and putting your biases aside. Seeing people as people who matter as much as you do. It’s amazing how much of a difference having a culture of inclusion and belonging creates. Google did a study quite a while ago now to figure out what creates the most productive teams and what they found was psychological safety was the number one thing. If you don’t feel comfortable coming in and being able to speak your mind and help things go right to say, “I’m seeing this,” or bring new ideas to the table, that psychological safety piece is one of the biggest things that keep companies from achieving their results in performing. It’s all connected and we’re helping companies overcome those problems.

I think you’ve touched upon a very important point, which is the inward versus the outward mindset. A lot of times, especially at workplaces, I personally experienced it myself when I was leading and building a marketing team. There is always this constant pressure of delivering on the pipeline goals, the metrics as well as, “Where are we at in a critical launch that we’re looking at? There’s a major new branding and our website redesign now, where are we at?”

There’s a constant stream of things that are being thrown at the marketing leader. Again, it depends on the environment and the safety net that it’s created by the leadership team overall, more often than not, that pressure for a marketing leader is being pushed into his or her reports. It also goes sideways in terms of the peers and that’s when a lot of the blame game and finger-pointing happens. Generally, it comes down to the inward mindset, which you did point out very aptly, Lisa.

Blaming others instead of taking accountability is one of the biggest red flags.

Blaming others instead of taking accountability is one of the biggest red flags. Click To Tweet

Who do you serve and what is your go-to-market like? I’m not expecting you to disclose any competition.

One of the things I’ve done since we got here is tried to narrow down our ICP fit because now it’s become a joke. Something I was saying when I was interviewing here is we should technically be serving anybody who has a soul. The sky is the limit. If you can see the humanity in others, then this work, if you get into it, should make an impact on you and your life. It’s not only in the work environment. It’s holistically. I’d say about 30% of our business is Federal government. Another 20% is in the public sector, state and local, and the rest is corporate. Again, we’re trying to keep that a little more narrow so that we aren’t boiling the ocean with our go-to-market to get started. This product can help anybody.

B2B 37 | Arbinger
Arbinger: Narrow down your ICP fit so that you won’t boil the ocean with your go-to-market to get started.


How would you define your go-to-market at a broad level? Do you have a sales team versus do you heavily rely on inbound versus a channel or partners?

We’re in build mode big time right now. We hired a full sales team to support our go-to-market. It was all referral-based up until probably mid to late-2022 and repeat customers. We’d bring in some new ones here and there, but it wasn’t like this crazy new inbound come there. There wasn’t much going on with the marketing effort there. Now, we’re looking to make it much more holistic. We’re building the account-based marketing revenue engine and we will be going outbound. We will also be trying to pull in more inbound, create more awareness, and start to grow again more holistically using a multiple-channel approach.

Lisa, we dive into what Arbinger does and what you’re doing at Arbinger around the go-to-market, and who you serve. It’s pretty cool stuff there. Something else that I ask my guests that pretty much everyone enjoys and talks about is the scenarios that entail both a go-to-market success story and a failure story. In your case, if you were to go back in time, what would you call out as a go-to-market success story and why? Also, your lessons and learnings from that.

One of my biggest successes was when I was back at Aprimo. At that time, we did not realize the extent of what we were doing, but we made an acquisition. Let me give you a little backstory. Aprimo was a marketing resource management newbie that created that space. It did not exist back in the day. They became the leader on the Gartner Magic Quadrant for thirteen years running in that space. Teradata acquired them for a crazy amount of money back then.

It then sat on the shelf for seven years in Teradata’s portfolio and there weren’t a lot of advancements made to the technology. They were only reaping the return on investment until it got to a point in which the marketing business unit of Teradata got to private equity. They sold the Aprimo entity and a few other small things bundled together and we went back to the name Aprimo, which they had purchased the rights for.

We pull out and basically, time had stood still for seven years with the exception of hundreds of thousands of customizations that were made because our technology was on-prem at that time. We’re in this rat’s nest of a mess and a whole bunch of new competitors came on the market at that time as well. One of those was called Workfront. You may have heard of Adobe acquiring them for $1.5 billion a couple of years ago.

Workfront came in and a few other competitors. They were SaaS. They were cool, UI/UX, slick, and everything for Aprimo was turned on its head. What we did was we acquired a company called DAM. They were a digital asset management company. We created a new platform and a whole new go-to-market strategy and story. We changed the whole space on its head because now we could integrate what you’re doing with your resources with the actual creative that you are producing and everything flowed. We also had a piece that could measure the ROI, even the amount of hours that were spent. Everything that you were doing against it.

The success piece of that was we became the leader again. We changed the whole landscape. If you look at the go-to-market maturity model, we were getting back into this, “What’s our product market fit? Do we even have one anymore,” to becoming the gold platinum standard for a platform in our space? It was amazing. It was pretty cool to be a part of that.

I’m looking at some of the numbers. While you were there, you took the company from $12 million AR to $50 million in three years. Those are some crazy numbers and growth for sure.

With private equity too, I’ll say it. We have a huge budget.

You also mentioned repositioning yourself and finding a new product market fit. How did that thought evolve? Can you dive into some of the details there?

It was a strategic part of the acquisition. When we looked at why would we buy this DAM, there were a few things that did for us. First of all, they were based in EMEA and we did have customers in EMEA, but it opened up that market for us. Second of all, they were more mid-market and we were more enterprise. It helped to bring together those worlds and expand our TAM. The third piece again was nobody else could do this. They had to buy 2, 3, or 4 different things to do what we could do with this integration. We had a platform story and a huge advantage, especially with the analysts. On top of that, part of that strategy was we also hired one of the analysts in the DAM space to come work for us. We went into it with a plan.

You and I know and everyone knows that go-to-market is not always up and to the right. There will be challenges and bumps along the way. If you go back in time, what would you share in terms of a GTM failure story?

From there, I went to 6sense. They’ve gone up to the right for sure. After that, I went to a company called Mindtickle. It was a great company and they’re still trying to figure things out there but the thing I think that was the fail there in the same vein as they were sales enablement, sales-readiness. This a platform that could not only ramp, train and coach your reps and your customer-facing folks but also measure success.

There was a grid. You could see, “Here’s where someone’s strengths and weaknesses are. Let’s give them this training. They’re not as good at objection handling.” They had a sweet spot and a good story and we got $200 million in nine months between two different funding rounds and new investors coming in. They had a different idea of what the go-to-market and what the product should be than the current. That was adding call recording.

I’ll say this was something hard-fought. It’s a huge market but it’s also a space the Gong and Chorus are. “There are established players in this space. Let’s stick to what we’re good at.” There was a vision of how this information would help feed this engine to be able to see someone’s capabilities in how they’re performing but it was like, “Should that be an integration?” It only became this huge distraction. A lot of resources and time went in into trying to figure this out. How do you position it? We took our eye off what we already had established as our product market fit and tried to create this bigger platform and go into this new market. It wasn’t our sweet spot and it hurt.

I can put myself in the shoes of yourself and the team there. It’s a challenge when the go-to-market is “dictated” by the investors. That’s a huge challenge. Yes, it’s a big market. You got big names like Gong and Chorus and going after call recording and sharing. Going after a pie in the bigger market is pretty attractive but the question then becomes, “What is our unique advantage, especially if you’re not in that space already. Why would someone consider us a “new name” or a smaller brand in that market versus more established players?

One of the stories I love is the HubSpot story where they were trying to go into SEO, blogs, and CMS. What they found was where they got the best ratings and where they were doing the best was in emails, forms, and marketing automation. They scaled back, focused on that, and now they have SEO components. They added a CMS. They can build on it, but they went smaller before they could go bigger. Again, when you have limited resources, where’s your sweet spot? Figure that out and build off of that.

B2B 37 | Arbinger
Arbinger: When you have limited resources. Figure out your sweet spot and build on that.


Now that you brought up HubSpot, which is a great success story. It’s amazing how they created a new category. They did focus on the specific like marketing, email, and forms that were their sweet spot initially early on but then they started going and telling the bigger narrative around inbound. They created this whole new category, which is amazing. What they’ve done is pretty inspiring, but that also leads to a lot of the “marketing leaders” and executives to start saying, “Why don’t we start doing a category creation model,” which is not the right play for many of the teams.

You and I have talked about that in depth. Most of the time, category creation is not the right answer. It sounds fun and exciting, but it’s a lot easier said than done. It can be a very big distraction and a huge revenue and resource strain. Do you need to do what’s always against it?

I think it’s Nick Mehta of Gainsight who mentioned this. Creation looks very attractive, but keep in mind, if you are going in and you need to go all in, then estimate about $5 million or even $10 million hot cash being put into that, plus all of your team, energy, and resources. Even after all this, even after putting in for so many years, there’s no guarantee you’ll come out fine.

I’ve talked with Nick about that and I’ve done the Play Bigger. I’ve gone through that and the workshop. I even looked back. I think Aprimo was the closest to that. Back then, category creation wasn’t that big of a thing but I look back and I’m like, “That was probably the closest ever I came to doing that.” We talked about it and we spent millions of dollars on the acquisition first just to create the platform and then we had to put everything into making it work.

Coming back closer to home and more towards your inspiring and amazing success story, Lisa, what would you call as 1, 2, or 3 superpowers when it comes to go-to-market?

There are a couple of things. I would say first, I’m very data-driven and it has served me well. Back to even just understanding my audience and what makes them tick. Looking at the data and having intent data, doing A/B testing, seeing what’s working, and what’s not working, but also being able to then convert that into ROI and CAC. Also, present that in a way that’s, “This is the data behind this.” Going to work for Teradata when I did, the CMO I worked for back then, her name was Lisa Arthur. She wrote the book Big Data Marketing and that was what our division was building and it was new. I feel like I’ve always been at the forefront of innovation, new technology, and these types of concepts. It’s served me well.

Building off of what you shared, there have been a few mentors, advisors, and people that have played a big role in your career success. Who do you call out as really pivotal?

Lisa was great. From there, I worked for someone named Ed Breault. He is still the CMO over at Aprimo. He inspired me. Not only is he an amazing leader. He brings out the best in people, but he was always leading edge and he knew how to position things. How to win over the hearts and minds of the entire organization. We made a transformation to account-based marketing using 6sense before it was a thing.

He got everyone on board with it. I’m watching how he did that. We still talk periodically and he’s been a great inspiration to me. Also, being a part of communities. I’ll say the Peak Community has been a life-changing organization for me. It has made the biggest difference. It’s blessed the day-to-day. I would say it’s more the big picture and the relationships I’ve made and people lifting each other up. Always have someone to go to if I have a question. Someone who’s always willing to help. It’s been a game-changer.

Always have someone to go to if you have a question. Someone's always willing to help. It will be a game-changer. Click To Tweet

I totally second that. I know you and I first met through Peak, but having said that, Peak has played a very important role even in my own life, especially in terms of who we can lean on. For example, I was looking to build a marketing strategy for a startup and I want a different set of eyes to look at it and give me feedback, an outsider perspective. There are folks in Peak who are ready to jump in on a call and then give the feedback. It’s amazing. Plug for Peak. I think it’s natural and it’s important. Our readers who are interested in and committed to growing your go-to-market and marketing career, definitely look at the Peak Community.

Reach out. We can give you a link.

Reach out to me, reach out to Lisa, or anyone, for sure. The final question to you, Lisa, is if you were to go back in time, what advice would you give to your younger self?

Have faith in yourself and go do what you want. Don’t wait for a time when you’ll wish you had started earlier. Click To Tweet

I think the biggest thing is that I can do it and have faith in myself. I feel like I’ve second-guessed myself a lot and part of it was because of where I came from, but I don’t know that it would’ve mattered. It was not having full confidence. I might put on the game face, but deep down, I was always second-guessing myself. Over the last few years, I’ve finally gotten to a place where I’m like, “I can do this. I see it. I can see the big picture. I know what needs to be done.” I finally feel like I’ve gotten to a groove and a rhythm where I’ve got even the right resources and the people. All the things are in a place where I can enjoy what I’m doing. I wish I would’ve started earlier.

That’s a key piece of advice. Even now, I have been feeling the same, which is, do I have everything within me and myself to do what I’m setting out to do this year in 2023? I’m doing something different and something bigger. There’s that constant “Imposter syndrome,” which we always face. Again, coming back to folks and coming back to your support group, this is where having someone like the Peak Community and even others like your friends and family plays a big role. It’s great chatting with you, Lisa. Good luck to you and your team at Arbinger. Have a wonderful day.

You too. Thanks, again, for having me.


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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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