B2B 9 | Product Marketing

B2B 9 | Product Marketing


There is one undeniable and undisputed truth in business: if people have tremendous experiences using or buying your products, they will probably stick with you no matter what. And by knowing which product marketing strategies to put in place, no one can stop you from achieving favorable customer feedback and higher revenues. Kyle Lacy of Lessonly joins Vijay Damojipurapu to explain how offering excellent product experience and finding the right target market can lead to a major win for any business, eventually achieving a “forever orange” status. He also emphasizes how to properly align marketing and sales, which can improve not only business operations but the way employees and partners connect with one another.

Listen to the podcast here


Kyle Lacy: How Innovative Marketing Strategies Can Change Your Business Growth

I have with me Kyle Lacy who’s a CMO at Lessonly. I’m super excited. I looked up Kyle’s background and I said to myself, “I definitely have to get Kyle on the show.” The reasons are number one, you have a very storied and accomplished career, all the way from being a Founder to being part of an IPO, part of an acquisition. You also are now running marketing, not like a typical marketing organization but someone who’s responsible for revenue, which is unique in the B2B SaaS industry. I also liked the aspect that you are a three-time published author. Welcome, my friend.

I don’t think I’m going to live up to that intro. Thank you for having me. I am a three-time published author. I would not recommend picking up any of the books because they’re out of print, but if you want to go learn about Twitter marketing in 2012, it’s a great book to pick up.

I’m sure all those basics still apply. Since the show is all about go-to-market. My signature question that I start with each and every guest is how do you define go-to-market?

A lot of go-to-market is defined by the top of the funnel and net new revenue. We look at go-to-market full cycle at Lessonly. We have an inbound team, an outbound team, and a team that focuses on customer marketing and expansion. For us, go-to-market is about repeatability and an amazing experience. We focus as much on the design and the experience of the brand as we do demand. That is a very fine line and it’s hard to balance. The goal is that you are driving growth but also making it a beautiful experience.

I’m curious, one thing that you didn’t touch upon and I want to pick your brains on that is talking about the product and the user experience of the product. Can you expand on that as well?

It depends on what your model is. Now, product-led growth is on the tip of everybody’s tongue. You want the product to lead, and sales and marketing to follow. Lessonly is a sales-lead company. For us, it makes the experience great on the front end for the prospect. The product is so easy to use that the experience is great when they first stepped foot into the product, and then continue to make the experience great, and I got this from ExactTarget where I spent some time, surprising and delighting your customers. If they get a random box of goods from you that’s all personalized to them, that is surprising and delighting them that your competitors will never be able to handle.

When I say an amazing experience, it’s from the chat on Drift on our website, all the way to the implementation of the product, to the usage of the product. If we can’t retain them and expand those accounts and those customers, we’re not a viable SaaS model. It’s very important. We have to remember that all these customers are not accounts. They’re humans. We try to apply that as much as possible to how we market Lessonly from pre and post-sales.

Being in a business and building a community requires empathy, with people all riding one single boat. Click To Tweet

It’s all about the full loop. It’s not the traditional funnel as we know, which was more about a decade ago. That’s gone. That’s extinct. Let’s switch gears a bit over here. I want to understand how you grew in the various roles. What did you take from each of the roles? You started off as a founder. You had your own company, and then you switched from being a founder to an employee from a VC perspective, as well as how you advised and how you grow in a marketing capacity. Can you share some insights and lessons from that?

I started an agency and that’s where I wrote the books because I learned that fake it until you make it is a very real thing because I was 24 years old trying to sell something. When we started the agency, we were doing design work. I was designing logos and brochures and all this stuff that you think about. We realized that we were getting beaten by everybody in the sales process. That’s when I learned the value of pivoting. For us at the business, it was, “What can we sell that people will listen to us?” That was social. It was talking about Myspace. We sold our first product to this company that was selling Myspace pages to churches.

We didn’t sell any. We sold zero of them. What that led into was consulting and teaching people how to use Twitter and LinkedIn and all that stuff. Building a company, I learned the value of pivoting and also the value of what ego plays into a sales process. There’s a fine balance with how much ego plays into your self-worth. Personally, I put way too much self-worth in my early twenties in my professional career. When we burned the business to the ground, I took a huge hit mentally from a mental health perspective. I learned very quickly you should not put your whole self into work, even though I don’t think I’ve learned that very well.

ExactTarget was a customer of mine. We had a thought leadership team. That meant we did a ton of research, a ton of content marketing when content marketing was not cool. We spoke at a bunch of conferences. Through ExactTarget, I learned the value of culture at scale. The year I joined, I’m positive we hired 500 people. What was brilliant about ExactTarget and the Orange culture, which what it was coined, was it didn’t matter how big it was. Our customers were talking about it. We were talking about it. There’s a Facebook group that’s still active that has 2,000 people in it. That’s called Forever Orange.

It’s learning culture at scale, which we’re starting to apply at Lessonly as well. At Salesforce, I learned the value of brand. You can love it or hate it but that is a marketing machine. I also learned that I don’t want to work for 50,000-plus person companies. In Lessonly, overall it’s empathy. It’s the number one thing I’ve learned. It’s how are you empathetic to yourself, your team, your customers, your prospects, and remembering that we’re all in the same boat here. We’re all human. We’re all trying to buy and sell stuff. It’s very important that you take that into account when you’re trying to build a company because it’s ultimately a community. That’s a very long answer but those were the points, the pivots.

That’s exactly what I was looking for and what my readers will value as well. Thank you for sharing. Thank you for being honest. Not many people are comfortable in disclosing and stating that, “I burnt myself to the ground when I started my own company.”

B2B 9 | Product Marketing
Twitter Marketing For Dummies

I’ve done that a few times. A lot of my self-worth is in my professional career. I don’t think that will ever change. It will never change. It’s something that fuels me. Through that process of owning a company, I realized that you have to have a team. You have to be able to support that team. You have to be able to make sure that the team believes in the mission and values of the company. If you can’t do that, it’s going to be very hard for you to scale. That’s what Lessonly has done extremely well. We have core values that have scaled from 15 people to 215 people.

At the same time, if you go back to the time when you founded your agency, back then you didn’t have revenue yet. You’re trying to figure out or you’re hoping that it’s branding, and that’s something that you can offer as a service. That’s not what the market is willing to pay you at that time. How did you find your first set of customers and revenue stream back then?

There was me. The value was I learned personal branding. I learned the value of building a community and a network of people, but it was just us. I taught myself graphic design in school. I didn’t go to school for it. I got a marketing degree. When I graduated, I started doing logo designs. This was before you could go buy something on Design Pickle for $55 that looks better than what I was doing.

Also, do something on Canva.

I’m glad that I did not start a company like an ad agency. At that time, we were selling accounting firms and manufacturing companies and all that stuff. It was a matter of what story can we tell that people resonate with. In 2009, 2010, social was a tsunami. It’s a value of understanding where the market’s at and taking a risk. We took a lot of risks but that’s part of owning and starting a company.

It’s all part of your life learning and life lessons. That’s what it is. Something that you didn’t touch upon and which I want to get your thoughts around is you also work at a VC company and initially, you’re doing marketing there. After that, you switched and transitioned to being a marketing advisor.

I forgot OpenView. That’s like the most learning I ever got in my entire career. I’m sorry, OpenView. I do respect you and I love you. You know I do. When I understood that Salesforce is not going to be for me, OpenView who’s a Series B venture capital firm out of Boston recruited me to run marketing for the firm but also consult the portfolio companies. We went through a rebrand for OpenView. I got an MBA in SaaS working for a venture capital firm that understands how to grow companies. I want to put a period on that. A venture capital firm that understands software companies is very important. You got to see the inner workings of all these software companies. You got to see what grew and what didn’t, what leadership worked and what did it. For me, I saw a market leader in ExactTarget. The year I joined, they had already won the market. We hired 500 people that year. With Salesforce, I saw what it takes to build a giant. At OpenView, it was A and B rounds. I fell in love with the A and B round stage and that’s where I’ve stayed.

There is a fine balance with how much ego plays into your self-worth. Click To Tweet

That explains why you are at Lessonly now.

Lessonly is a portfolio company of OpenView. I highly recommend anyone that wants to get into executive-level leadership at a software company to spend some time in a venture capital firm if you can do it.

How did he get that role? Was there a lot of networking, cold calling or cold emails?

It’s all about networking. This is the importance of building a community and mentorship. When my company was failing, I had met Scott Dorsey, who was the CEO of ExactTarget at the time, at a community event. We had both gotten 40 under 40 for the Indianapolis Business Journal. I met him at an event and I randomly emailed him and said, “Scott, we met for 30 seconds. I need your feedback on a problem I’m having with my business.” He spent 45 minutes on the phone with me driving home from work one day. Every single career decision I’ve made from that point is because of Scott, just because of that phone call.

Scott was CEO of ExactTarget. We were bought by Salesforce. Scott Maxwell, who’s the founder of OpenView, was an investor in ExactTarget. When they sent a note to me that they were hiring a director of marketing, Scott Dorsey pushed me towards that. I’ll never be able to repay him because my entire career is built off of that one phone conversation we had. For OpenView, it was a good referral and Lessonly is an OpenView company and Scott Dorsey is on the board of Lessonly. It all comes full circle.

It all started with that 30-second conversation.

B2B 9 | Product Marketing
Product Marketing: In go-to-market, there is a fine line between brand design and experience.


I’m glad I didn’t screw up in that 30 seconds.

Let’s dive a bit more into how you structured your marketing organization at Lessonly. I know we chatted a bit about this earlier. Expand that. What is your whole thought process around marketing being responsible for revenue and how are you doing that now?

We measure everything by direct source like what was the first touch in a certain timeframe. For me, I had to be able to own a huge chunk of that direct source revenue because when you do, you have a seat at the table. It is very important for creative and brand-driven marketers to have a seat at the revenue table because then you can do creative and brand-driven campaigns. We’re very lucky that when I joined, they already had a pretty strong organic strategy. For us, we set the team up in stages or even channels. We have an inbound team. We have an outbound team. We have an expansion and experienced team that has to do with customer marketing.

The goal initially was, “Let’s figure out inbound. Let’s get inbound working and growing. Let’s figure out what’s blowing up the website and redo it.” At the same time, we brought the BDRs and SDRs under marketing. We have a commercial segment and enterprise segments. We have two teams and we did that for a lot of reasons. The main reason was to force alignment between marketing and sales. The reason that you want to own a revenue number and you want to be responsible for revenue numbers in marketing is threefold. Number one, you want to have the bandwidth to be able to do creative things. We can launch a clothing line.

We can do a board game. We could do a golden llama. We can do a user conference because we support 60% of net new revenue as a marketing team. The second thing is sales and marketing alignment. If you are producing the revenue, there is no choice other than to align because if you don’t, you guys are lost. We’re all lost. The third reason is that seat at the table so that you have the ability to ask for more budget, to build out more budget, to make decisions in a way that’s meaningful and not just because you’re a brand and communications team.

Let’s double click on that marketing and sales alignment piece. Personally, I’ve seen that as a challenge in my other roles when I was looking for other employers. At the same time, that’s been something close to my heart in the last couple of years where when I was doing and leading marketing at a Series A company, it was all about marketing and sales alignment. Yes, marketing can generate all the MQLs. Let’s not even talk about MQLs right now. That’s a whole different story. Even if you generate all the leads, somewhere, somehow things would get dropped then passed back over to sales. It’s not that it’s intentional, but things happen. Talk to me about how you are creating and enhancing that marketing and sales alignment. Does it start with BDR under marketing or is it a lot more than that?

It goes to what we were talking about before. If you source 60%, 70% of revenue for a sales team, they’re going to align to you. Shared definitions, like marketing qualified lead. There are a few other forums out there, but we have one form on our website and that’s request a demo. We don’t feed content leads to the sales team. Marketers do not feed content leads to the sales team because you’re going to screw alignment up. I hope that nobody’s doing that now. I hope that we’re far beyond that, but I know that we’re not.

A team must believe in a collective mission and values. If you can't do that, it will be very hard to scale. Click To Tweet

Are you talking about data content?

Yeah. Just because somebody downloaded an eBook, it doesn’t mean you need to put a headcount on following up with them. Open it up. Dave Gerhardt said this years ago. I don’t need to rehash this. It’s a shared definition and it’s also meeting weekly. We have a funnel and pipeline meeting that we meet every week and it’s all the revenue leaders. It’s CX, sales, marketing, and it’s run by revenue ops. We go through the pipe, the goals, the metrics, and that aligns everybody. Even if it can be tedious, you’re at least seeing everybody weekly. For me, that’s the main thing. It’s being open and asking clarifying questions. It’s making sure that you are communicating appropriately and effectively. You have to be joined at the hip with the sales leader. There’s no other choice. If we were doing great events and direct mail, you’re just an afterthought.

Neither would you have a seat at the table because that’s not directly sourcing revenue.

They’d put me under a CRO or something. We don’t want that.

Let’s talk about product marketing. You didn’t mention about product marketing, even though it has the function and the second word in that is marketing. Somehow it doesn’t appear under marketing. Why?

We’re pretty unique in the fact that we have a very large revenue enablement team. The way that our revenue enablement team is built out is that it has sales engineers, solutions consultants, sales enablement, and we added product marketing. The reason why is because it is the center point of all the revenue teams. It lives in between everyone. If you want alignment, it pretty much comes out of the revenue enablement team or revenue productivity or whatever you want to call it. When we were looking at product marketers, you might have questions about failures. Maybe I’ll save this for the failure section. It made more sense to house the product marketer there. Product marketing, because of messaging, positioning, competitive analysis, lives within revenue enablement

B2B 9 | Product Marketing
Product Marketing: If you are producing revenue, there is no choice but to align. If you don’t, everything would be lost.


Typically, product marketing does all those things, which includes positioning, messaging, competitive sales enablement, but there’s also the piece around the launch. There’s also the piece around go-to-market strategy and execution. Who does that?

That is shared between marketing sales and revenue enablement.

It makes sense because Lessonly is primarily a sales-driven organization.

We don’t have a free trial. We’re sales-led. For me, it’s how do you continue to build the product into campaigns and messaging and make it fun. We’re working towards that. We have a great product marketer that joined us. I’m excited for us to continue evolving that.

You mentioned that in Lessonly, you moved all the way from SMBs or mid-market to enterprise. That transition is hard. A lot of companies cannot make that transition effectively, or they’re stuck and they focus on one vertical. How did you make that transition and what are the lessons learned there?

Just a clarifying point, we added enterprise, we didn’t transition. We still have a commercial segment, SMB segment, bread and butter, repeatable. It works well. I have a lot of learnings for moving up market, which we could spend an hour talking about. For us, number one, we put sales headcount towards it. If memory serves me correctly, we had two commercial/mid-market reps that we thought would work well in the enterprise. We moved them into enterprise and we created an enterprise sales unit. We had enterprise SDRs. If anybody’s thinking about doing this, you need to take notes here. You need more than two sales reps to try to figure out if something’s going to work or not.

For what we did, it worked for the most part but if we would have taken the bet and risked it and hired two others and had four enterprise AEs, we would have learned more. We would have had more data. We would have been able to make better decisions. The second thing is product marketing. We didn’t have a product marketer. If I would have pulled the trigger and hired a product marketer years ago, it would have been an easier transition for us because it has all to do with messaging and business outcomes and all this stuff. It was not built into our DNA as a company to talk about that stuff. The biggest thing is you have to make the commitment and it is not cheap, both from a headcount perspective as well as a budget perspective.

You cannot apply a commercial go-to-market model to an enterprise go-to-market. Click To Tweet

From a timeline perspective, it took you probably 18 to 24 months before you started seeing the learnings, and then applying those learnings.

We started seeing revenue twelve months in, but not from post-sales. It is amazing. The implementation team, the services team, the account managers. Go-to-market, we’re about 80% of the way there, so 24 months. It depends on sales cycles as well.

It all boils down to the difference in the go-to-market motion. When you talk about go-to-market for mid-market versus go-to-market for enterprise, it’s different but it does. Number one, the deal size is different. It’s bigger. Second, it’s a complex sale cycle. It’s a lot of touchpoints, be it buyers or influencers on a committee. You also need to have a lot of educational material, which almost borderlines branding and awareness. It’s all of those pieces.

You cannot apply a commercial go-to-market model to an enterprise go-to-market. It’s the difference between we know we know how many demos we need to get in commercial to confer X amount of ARR. We’re in a named account model and enterprise. It’s very different. You have to have prioritization and understand what you want to accomplish. Go-to-market is easy compared to the product when it comes to enterprise. The amount of time and energy you have to spend trying to figure out like accelerations and the roadmap and all that stuff when you have huge deals come in, it’s a walk in the park for go-to-market compared to what product has to deal with.

I’ll challenge you a bit on that, Kyle. The reason being when I say go-to-market, it includes product. Somehow, there’s a notion that go-to-market is mostly marketing and sales and then customer success, but then it starts with the product. The product plays a key role because if you expand go-to-market, you need to, first of all, understand the market. The features and the road map will then line up to the product. That’s my little mission behind this whole show. I want to expand that whole thought process in the industry. I don’t know how successful I will be, but there’s this notion of any talk about go-to market is mainly marketing and sales.

It depends on the product. If we’re talking about Expensify, Mailchimp, Calendly and Postscript, that’s product growth. The product is first. We could talk about that all day long because that’s the future of software if it’s not already here. I’m 100% in agreement and marketers need to understand that.

B2B 9 | Product Marketing
Product Marketing: Marketers do not feed content leads to sales because you will screw up the alignment.


What are your big goals for 2021?

For us, it is fully understanding what it means to support a sales team and customer service team when it comes to sales readiness and coaching. That’s what we sell. We focus on everyone from a software sales team all the way up to a huge call center. Number one, it’s understanding the market. Number two, it’s getting back to the routine. After 2020, we have over 200 employees and the majority of them are in Indianapolis, and we were all in an office together. Despite the fact that it’s been some time now since we went remote, there’s a lot that’s changed. There’s a lot that happens when you’re all remote, even from a hiring process. The majority of our jobs now, the people are probably not going to be in Indianapolis.

For us, it is continuing to evolve the product and positioning because that’s what you do if you want to stay ahead. Understanding the remote culture and making sure that we are being community-oriented to everyone, not just the people in Indianapolis, especially when we go back to the office. Number three, it’s evolving and being more creative as a marketing team. We will constantly try to do that. That’s what makes this whole thing fun. If you want to do a board game, do a board game. If you want to do a user conference, do a user conference. I love Dooley’s webinar where they make people eat hot sauce and answer questions. Stuff like that. We got to have more fun in B2B marketing. The B2C marketers are looking at us like, “Come on, this is boring.” You’ve got to be more consumer-oriented, in my opinion.

Think of it this way. B2B, you’re selling, you’re doing business to business, but at the end of the day, it’s humans who are the buyers.

Here’s another one. Don’t send me a blanket, a t-shirt or a Yeti bottle. That’s it. That’s my 2021 thing. Don’t send me crappy swag. If you’re going to send me something, let’s do this right. 2021, the year of cool swag. No crappy swag. For those of you who are reading, that is a joke, but please don’t.

When it comes to talking about those, you mentioned about expanding or strengthening your messaging piece, strengthening your sales and support. If you were to have an extra budget, who would you hire or where would you invest in and why?

It’d probably be on the customer side, the customer marketing. We have a great customer community called Lamination. That’s a mobile app. It’s awesome. It’s highly engaging and more support there. Customer marketing partnerships and expansion, that’s where I would focus if I had more budget.

In order to make B2B marketing more fun and productive, it must become more consumer-oriented. Click To Tweet

Let’s move on to the closing segment over here. I got a bunch of questions here. If you were to look at the industry across over to your peers, who would you call out or who would you do a shout out to as someone who’s executing the go-to-market very well? I know you mentioned Dave Gerhardt. We talked about Chris Walker in the B2B space. Besides those and in addition to those, who would you call out and who would you give a shout out to?

For sure, and not because he’s a great marketer because he’s a brilliant human being, is Anthony Kennada. He’s the CMO at Front. He was the CMO at Gainsight. He grew Gainsight from $0 to $100 million in IPO. He truly understands this idea that there’s a human element in all that we do as marketers. He does it in a way where it seems easy. I have a lot of respect for him. A lot of respect for Ryan Bonnici, who’s now at Whereby, who was at G2. I worked with him at ExactTarget. I could rattle off tons of people. I have two more. Jeff Reekers who’s the CMO at Aircall. He’s an amazing person. Andrea Kayal who’s the CMO at Electric.

I’ve heard of Anthony. I have not heard of others but after this, I’m going to make a note for myself and look them up and study them. That’s something that I’m doing here on the show. I want to host the good talk leaders. It’s a butchered term, by the way. People who think from a human perspective, be it whatever function.

Jeff and Andrea would be great. They’re great human beings.

I’m going to reach out to them. If I have trouble, hopefully, you can do an introduction.

If you want me to introduce you, you’re going to have to remind me, though.

B2B 9 | Product Marketing
Product Marketing: You need more than two sales reps to figure out if something’s going to work or not.


Thank you. My last question. If you were to go back in time to your first day when you’re doing go-to-market, it’s probably when you are doing the agency. What advice would you give to your younger self?

This is what I would say and I know I wouldn’t accept it as a 24-year-old. It would probably be, “Don’t take things so seriously. If you lose a deal, don’t let it ruin your weekend,” but I know myself well enough that it wouldn’t change anything. I would probably say don’t take things too seriously. For me, I love what I do so much that it is part of me. I will always work in marketing. I’ll always work in software. I will build businesses until the day I die. Don’t take things too seriously but also have fun is a better way to frame it. Earlier in my career, I was so focused on succeeding that I didn’t have fun. There are positives to that. I worked extremely hard but I feel like I aged twenty years when I was 25.

Lucky you and clearly, you’ve come out with a lot of humility from that whole experience. I can see that in you as a person. I also see that other aspect, which is a lot of times, especially in our society, we associate success with monetary gains, awards or rewards, but if you dig deep, a lot of success comes from failures.

It also comes from building great teams. I love seeing people that I managed at ExactTarget in leadership roles. Tim Kopp, who is the CMO at ExactTarget at the time. Now, he’s CEO at Terminus. He has over ten people that were on his team that are all CMOs. That’s what I want to do. The whole reason you want to be a leader is to build people up and see them succeed in the future. That’s why I do it, other than the fact that I love marketing.

I know we’re coming up on time. I can go hours and hours on this and I can see that in you as well. We should do a redo and come back at a later point in time. Thank you so much. It’s been a pleasure and I’m wishing you and Lessonly the very best.

Thank you so much. I appreciate it.


Important Links


About Kyle Lacy

B2B 9 | Product MarketingServes as a Chief Marketing Officer at Lessonly, a training and enablement software company based in Indianapolis, IN. The team consists of amazing designers, growth marketers, customer marketers, field marketers and inbound/outbound sales reps.

I apply the lessons learned while working at a venture capital firm, an IPO, an acquisition by one of the largest software companies in the world to drive revenue at Lessonly.


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B2B 8 | Go-To-Market

B2B 8 | Go-To-Market


Businesses go from one level to the next. The further you are along, the more complex your business strategy will become. In terms of the go-to-market, startups and mature businesses also differ in their approach. Taking us through these stages, Vijay Damojipurapu invites Ajit Deshpande, the Vice President of Demand Generation at Marqeta, Inc. Here, Ajit shares his thoughts and observations between startups and businesses that are further along in the game and reveals some of the best practices of go-to-market leaders. He gives pieces of advice to leaders on building traction and scaling up—from marketing to leading a team with experimentation—and then reveals how they are working towards their goals in the company as a FinTech startup. 

Listen to the podcast here


The Go-To-Market For Scaling Startups With Ajit Deshpande 

I have with me Ajit Deshpande, the Vice President of Demand Generation at Marqeta, who is based out of Silicon Valley. Ajit has a unique profile and track record in the sense that he has grown in the ranks and in the roles of go-to-market oral function all the way from marketing planning, business operations, marketing leader role, now in Demand Gen. At the same time, he’s been active in the whole startup ecosystem. I’m looking forward to the conversation.

Welcome to the show, Ajit.

Thanks, Vijay, for having me.

I always like to start off with the real key question around the whole theme of this show which is around go-to-market. How do you define a go-to-market?

When you think of a corporate entity in any company, there are two main roles that exist in the company. One is the role of making something, whether it’s a product, service, software, or whatever and then there is the role of selling it. When you boil it down into those two things, go-to-market is the second half. For something that exists, how do you find the right customer for that product, service, or the solution that’s been made? Finding the right customer, reaching out, selling, retaining the customer in the long-term, and then hoping that the customer becomes an evangelist. That whole process or gamut is go-to-market. When you think of it in terms of corporate functions that will then contain marketing, sale, customer success, deployment, and it will include support operations. A lot of these teams work together to get the go-to-marketing going. That, to me, is a go-to-market.

I like the broad perspective that you bring to the table. This is a common theme that I’ve seen occurring with the go-to-market leaders I’ve been speaking with. It’s always a very holistic and broad perspective. The reason why I share this is I myself have been guilty of this whole process years ago when I started in product management or even a product marketing role. For me, back then, go-to-market is all about how to get this thing out of the launch door. It’s all about the launch process but over the years, my perspectives and insights have evolved.

It’s in line with what you shared and the various guests have been saying as well. It’s an inside view but at the same time, and more importantly, an outside view of, what is happening outside the company and how we tie those two things together? As you said, you build and innovate but how you take it to market. It’s an ongoing process. Share with the audience about your journey, how you started specifically go-to-market role? If you go back in time, how did you evolve your journey and how did you land at the role that you’re in now?

I’m an engineer by education and training. I studied mechanical engineering in India. I did my undergrad there then I came to the US.

You did your undergrad from one of the top Institutes in India.

At the Indian Institute of Technology in Bombay is where I finished. I immediately came after my undergrad to Stanford to do Master’s in Mechanical Engineering. I’m a hardware engineer by education. After that point, I did another eight years of engineering work all in the Bay Area in Semiconductors and then in Cleantech. I was a robotics engineer. I designed robots for these industries and it was all great. It’s quantitative, solid work, and satisfying in its own silo, so to speak. Part of it, for me, was I didn’t understand what happened after my work was done.

Marketing is just making the right offer to the right person at the right time. Click To Tweet

These robots then got integrated into other systems. That system then would get sold to a customer. The customer would make chips and then those chips would come back to me through our laptops and then phones. It was a little bit of a roundabout existence to connect what I was doing, the end outcome for the consumer. I was always curious as to what being closer to the customer’s need and customer validation might feel like. I did go to business school with that intent, which was to transition out of engineering and into more of a business role. I didn’t know what I would do in business. I wanted to explore it. I went to Berkeley towards the end of the last decade and did my MBA there. During this time, I originally explored finance as a function.

I looked into multiple different streams within finance, investment banking, I did some Hedge Fund work, venture capital work, and I was doing all of this pro-bono exploration during business school. I realized that it was the technology piece of it that was still exciting to me. I tried my hand in venture capital and recruited into it heavily. I was able to get into the VC world at a firm called Opus Capital back in 2012. As it turned out, none of my hardware experience mattered because Opus focused on software investing for the most part even though it was B2B enterprise. They hired me partly for my drive and my perceived potential to figure things out.

When I went to Opus with all the hardware experience that I had, I had to learn everything from scratch. I had to learn about databases, networking, mobile SaaS, etc. In that process, what was logical for me was to look at all of these early-stage investment opportunities that the Opus came across. I came across from the lens of how these ideas would scale and get taken to market because I was not necessarily a technical architect that would get into the weeds of the product based on my previous experiences. The go-to-marketing came second nature to me as I was looking at startup. As I was doing that, I had a lot of these notions that are developed on how marketing, sales, and customer success might behave.

After two years of doing it, I started questioning whether I had the right notion in the first place. I decided to move from venture capital and try to get into the business side in a functional role. As I was recruiting, I was hired by Salesforce back in early 2014 onto their marketing team to lead business planning. I would never have expected myself to be a marketer at that time. For me, marketing was like any other aspect in go-to-market. It’s big in many ways, unsolved problems. You could think of it as a challenge and with first principles, you could solve all of that.

I thought it was an excellent opportunity for me. I went to Salesforce and marketing and then I spent five and a half years there learning about various facets within marketing whether it was the business planning piece that I started with or over time I scaled into various other aspects, mostly on the marketing operations, analytics, and strategy side but then in the process, I got exposed to marketing quite a bit. More so, I got exposed to a lot of top-notch people at Salesforce that is at the forefront of B2B marketing.

I learned a lot from them. I understood their psyche and my own psyche, so to speak, and I got more and more interested in that piece of it. Later on, I went from Salesforce to Stripe. A lot of it was driven by a couple of objectives. Number one, as I understood Saas to be an excellent go-to-market business model, I also had this notion that with all the consumption-based aspects that were happening in the FinTech world, that things might be different and interesting to understand. Stripe was one of the key companies that have been driving that thought process forward. I was at Stripe for a year where I was more in the finance team that supporting sales and marketing.

In that sense, I involved in go-to-market strategy but from the financial angle. After a year of doing that, I transitioned to marketer which is also in the FinTech space, smaller startup than Stripe but a leader in card issuing as the category. With that transition and back into the marketing role where I’m now responsible for Demand Gen, I go from high touch events to account-based marketing, inbound online paid, Demand Gen, SEO, and to marketing ops. A much broader scope across Demand Gen and it’s a way for me to contribute to this company’s success.

That’s a great journey there. I can go into several of those areas and we can have a deep dive discussion around those for the value and benefit of the audience. You clearly being very closely associated with the go-to-market when it comes to early-stage startups. When you were at Opus, you are seeing that and evaluating businesses from that point of view but at the same time, at the other end of the spectrum, you have been very closely involved with go-to-market for the more mature businesses at Salesforce and Stripe, and now at Marqeta. What are your broad thoughts, paradigms, or observations that you see on early-stage versus more mature?

One way to boil it down is that when you’re on early-stage or a small company, it’s pretty much hand-to-hand combat. You are going after that next customer, next small business, and next small vertical that used-case that you’re willing to put a lot of energy into winning. That’s the focus for a smaller company. What that also means is that the objectives are simple and the alignment across the go-to-market chain. When you think of marketing, sales, and customer success, everyone is extremely aligned on that objective. Once you go past a certain scale and you go into the large company more, you’re looking at aggregate sophistication.

B2B 8 | Go-To-Market
Go-To-Market: When you think of marketing, sales, and customer success as a startup, everyone is extremely aligned on their objective. Once you go past a certain scale and go into a large company, you will start looking at aggregate sophistication.


Before we go into more of the larger scale, it’s easy to get the alignment between go-to-market functions like marketing sales, success, or support but the challenge is there’s no playbook into how, which market segment? Who is my customer, who within the customer, how will I engage them, who is the buyer, what is the buying cycle look like, it might hit my revenues, and forecast? It’s all topsy-turvy at least for the first couple of years until we hit scale. Any thoughts on that?

That’s the beauty of innovation and being in a startup because you’re trying to do something that is brand new. The existence of the lack of playbook being in place is a logical outcome of your own pursuit. It is in some ways a competitive advantage to come up with the thought process and a playbook to create that winning combination for yourself. With that said, the absence of a playbook is somewhat compensated by the simplicity of the objective, which is I need to figure out which customers might like my product. How do you find that out? You interview five prospects and you find the one that resonates on your thought process. There is a lot of manual needs to the work and a lot of ingenuity that has to be brought in but at the end of the day, because the goal is a relatively simpler goal to go for, the efforts can still bear fruit.

That’s broadly my thought process. Number two, when you think of go-to-market, matter product, user experience, or any aspect associated with the business, the logical first principles-based approach to looking at any of these situations typically will be a winning approach more often than not. Marketing is making the right offer to the right person at the right time. If you could find the right person, you could make the right offer when they are ready, you will succeed. The question is, how do you get it done?

Simple concept but hard to execute.

It is very hard to execute but you can use first principles and say, “This is how I can plan my work to get the best of what resources I have.”

Clearly, you’ve been very closely involved in startups, not just from an operational but even as an investor and advisor. If you look back and step back, what do you see the common 2 or 3 top recurring themes as best practices and something that you would share with founders and go to market leaders for the early-stage startup? I’m talking about seed or even Series A.

Is it from the standpoint of go-to-market?


The few principles are objectives that any founders should have. I’m getting into a little bit of a philosophical thought process but hopefully, it’ll all connect together. Number one, one has to be extremely unbiased in their thought process. A lot of entrepreneurs and corporate individuals, entities are biased in terms of the potential for their product to succeed for what the customer may or may not want, etc. and that bias affects a lot of the decision-making. Can someone be unbiased in their thought process? Number two, always customer-centricity makes a difference. What does that mean? Any startup for success as to monetize what they are building. If what they’re building is not used by anyone then it makes no difference to the world that is a product.

Customer centricity always makes a difference. Click To Tweet

They have bigger problems in the sense of entity will collapse.

That could be but more so, every action for individual and founder has an opportunity cost. That opportunity cost is they could be doing something else. If they’re putting their time into solving a problem then that problem is something that the customer needs. Being customer-centric and unbiased, those would be your starting points. Again, going back to first principles. How can someone envision the future? Can you imagine where you’d be five years from now? Can you slowly peel the onion back from five years later? What does that mean for next year? What does that mean for three years from now?

What is my five-year goal? If my five-year thought process is to be the dominant CRM company in the world, then how do I create the CRM market? How do I get ready to sell into it? What products do I need? What will the technology landscape be in five years? To be imagining it, boiling it down, and bring it back to the eventual tactical outcome, that’s the third aspect of it. The fourth piece of it, which is personal for me but in the startup world, this is something that a lot of successful founders to practice in the first place. It’s always to be doing something, iterating, getting to the next step, not be thinking about something, big strategic objective, and rather small wins will combine together to get to the final outcome.

Going back your first point, it’s all about having that intellectual curiosity. That’s how I term it. When you say unbiased, you need to be sincerely and seriously honest with yourself and led data. Sometimes, not always data will dictate but you need to be intellectually curious and honest with yourself. To your last point, it’s all about the market pull you in that direction. Switching back and going down to the more scaling part of the business which are being closely involved on a day-to-day operational basis over the last few years. Continuing on your thought process there, we are moving the needle from go-to-market for early stage, which is all about building traction to now, you’re talking about go-to-market for scale up. What are your thoughts, lessons, and advice for the audience?

As a company matures and scales up, it’s filled by the nature of its evolution. It will start becoming a combination of a lot of specialized functions, so to speak. For example, at market, we have sales and BD team that exactly understands what our product-market fit is. At a very early stage, they can gauge pretty well whether a prospect is right for us to pursue or not and it saves us a lot of time from their perspective. We are not engaging with prospects, which will lead us to a dead-end because FinTech is a rapidly evolving business. Time is of the essence as far as getting product-market fit at scale. Our BD team is smart. Our marketing team on what we are doing is as full-scale as it can be for the resources that we have. What that means is we could do many different ways of getting to market.

We could have the website be extremely sophisticated. We could have big Demand Gen and scale. We could do SEO and account-based marketing. There are all these things which we do to some extent. For us, a lot of the goal is to try to create the right mix of effort from our side in order to match up with our sales goals. That’s the other piece. For me, as we look at marketing, the scale of the company makes a massive amount of difference. In a small scale startup, you could use one channel, one tactic, and that may be enough for you to feed your entire sales objective.

As you get to a marketer style thing, you are looking at more of a full-scale marketing effort that has elements of almost anything that you can think of within marketing but with prioritization and a mix of objectives or channels based on the skill that we are looking for. As you go further into a large company such as Salesforce, you’re doing everything at massive scale. You are doing everything from 60,000 people dream force down to an end event portfolio of hundreds of events, lots of digital marketing, a pretty sophisticated website, and so on. At that point, every single channel is a necessity. For a marketer, it is a question of prioritization.

You shared about the different go-to-market channels and Demand Gen avenues. You mentioned about ABM pieces including events, inbound, and outbound from a combination of email to SDRs and BDRs, and then the account executives closing the deal. What is your broader approach or what is the guidance to the team? When I asked this question, I think about you are given the charter for the next 3 to 6 months. How do you guide your team and what experiments you need to experiment, at the same time, you need to deliver on those across this channel? How do you approach and give guidance to your team?

Let’s start from the last part first and then I’ll get to the first part of the question. Experimentation is a cultural thing more than anything. What that means is at any given skill, you’ve got to be experimenting all the time. One utopian goal that we have, at least for myself, my team, and the product organization, is we would like to experiment with 10% of our resources all the time. What that means is if I have $100 to spend on digital advertising, we should be trying to invest ten of those dollars on things that we don’t know much about. We know for the future whether these things work out or not. On the fringes, there is value to having some investment in experimentation, always, in the perspective of what it is that you’re doing.

Do you report those on your weekly/monthly dashboard?

B2B 8 | Go-To-Market
Go-To-Market: The beauty of innovation and being in a startup is how you’re doing something that is brand new. The existence of the lack of a playbook paves the way for a logical outcome of your own pursuit.


In B2B marketing, it’s very hard to break out the impact of one piece against all the other things that are happening. The end goal is still an end goal which is we need to deliver leads and pipeline to the sales team. To the extent that we are doing it with the resources that we have, you’re okay. To the extent we are not doing it, there’s a problem. The point here is experimentation is more of execution on the scientific method. What that means is you have a hypothesis that something might be interesting and you put in some investment and some resources into it. If it works out, great. If it doesn’t work out, you move on and go back to what is the basics and what works for you. That’s one piece.

There’s two levels of experimentation. One is within a given tactic and then there is the experimentation around tactic mix. Should I be doing more online and less events or vice versa? It’s an experiment. It’s all the same money that is being invested across these things. There is a significant amount of art form to try to figure out what decisions will result in that mix shifting more time. That is part of the challenge and part of the opportunity for a role like mine. That’s number one. Your second piece was more around how Demand Gen, whether it’s events, ABM, or inbound, etc.

How does it align with your quarterly?

How to think of it in the context of the company’s objective so to speak? At least from my personal perspective, that part is more of a top-down thought process. The way that I personally look at it is in Demand Gen, sales have certain goals. That certain goal that is downstream on revenue translates to a certain goal upstream at leads, traffic, or conversion rates, etc. That’s the starting point. The next question is, what is the mix I’m going to use to achieve, what are goals that I need to deliver? That would be based on what has worked in the past and, correspondingly, where is it that I need to grow? There is always that eventual plug, which is the rest of it has to come organically.

You could call it a miracle, product-market fit, or some vitality in our scale or brand and all that. There is always an organic component to all that we do. Once we’ve figured out what it is that we are looking to shoot for, then the next thing is for us to make sure that there is resourcing across each of these key initiatives. To make sure that we all measure ourselves back with the understanding that at the end of the day, whatever it is that we are projecting is not going to happen. That will be some variant of what we think is going to happen.

However, the total of all of our mistakes will still end up to be zero. That’s what we are looking for. We are pretty much looking to, again, have that point of view to make sure that we are invested to feed or achieve the objectives associated there. For us, whether it’s the experimentation culture or the delivered results culture is to be this passionate. It’s to evaluate whether we achieved or underachieved because of intent and how much of that was luck. How much of the market is turning in our favor or against us is what matter. Look, evaluate, trade, fix more.

One thing is very clear based on what you’re saying, Ajit, it’s very clear in your mindset as to how you’re applying a financial portfolio management thinking into this. You mentioned about you win some and you lose some but the net game should be zero. It is the same mindset that you’d use when you’re building a financial portfolio. You’ll have some stocks or some investments where you’ll hit it right out of the park and others which can go downhill. At the end of the day, are you net positive? It’s the same mindset that you are applying.

I would extend that a little bit further. Every leader for every function thinks the same way or at least should be thinking the same way. Whether it’s the CFO of the company saying, “Should I invest in sales, marketing, or product?” They might same think, “Where is the biggest bang for the buck for what I have?” It’s the same thing with the salesperson saying, “Which deals should I put my energy into?” The product person is saying, “What features are important?” Every one of those things has that logic. I want to also say that every function has its own complexity and nuances.

Marketing also has those nuances. At the level of making decisions on what to do in marketing, such thought process make sense. At the end of the day, marketing is a very massive art form. Marketing needs the intuitive feel, brain, and gut feel of the marketer to be the right intuition and the winning field. That is very much driven by the marketers themselves being smart and more right than wrong and all that. The right people in the team make this difference happen. That skill, intuition, and thought process comes with experience and time. If a team has great people in it, it will be very fun.

FinTech is a rapidly evolving business. Time is of the essence as far as getting a product-market fit at scale. Click To Tweet

How big is your team? Can you also share some details around your MarTech stack?

The marketing guard at Marqeta is around twenty people. Demand Gen is 1/4 of 1/3 of it. The company overall is 500 people. As the whole entity scales, so with marketing, Demand Gen, and every that function within. As far as the MarTech stack, it is robust from the standpoint of addressing all the automation needs that we have but we still have some ways to connect all of the elements of the stack together. Our MarTech stack at its core is represented by three nodes. Node number one being the Salesforce, which is where sales puts all of that information. The question is, how do you break it down? Node number two is HubSpot, which we have data from all of our campaigns. This is how we have done all of our campaigns, whether it’s our email campaign or outbound campaign. All of that goes through HubSpot.

The third mode for us is Engagio, which is the entity that helps us consolidate the work that is happening on both sales and marketing from the standpoint of the end account. With Engagio, we can look at what meetings are happening, who’s coming to our website, who’s responding to our campaigns, who are we sending emails to, and all of that. Those are the three core nodes. Around those nodes, we have a lot of different MarTech elements. We have content delivery, project management, ad service team, and lead enrichment, and all sorts of things that would be required for a typical effective ABM program. The last piece for us, as I said, is continue to connect all of these together so we can have a more holistic view on an ongoing basis.

That’s an art form. How are you thinking about your goals or objectives? Can you share a bit about that?

From the standpoint of where we are as a company or FinTech startup, that comes a lot of companies with lots of transaction volumes as our key customers and also prospects for us to go after. As we look at our ecosystem of prospects, we are focused on high touch marketing as an ongoing thing. We are not as focused on super small business marketing. That is not the right product-market fit for us at this stage. Our goal is to keep figuring out better and more effective ways to convert our prospects into customers for these high volume type account. That’s our goal.

I don’t think that is going to change for the period of time. Within marketing as we evolve, we have a pretty solid MarTech stack that allows us to in silo be effective at any given tactic or approach. One of the big goals for us is to go from there into a true influence approach in marketing. Now, we can track success at every step but our goal is to look at the big picture in a one-click automated manner. That’s one of the big goal for us, number one. Number two, the goal to be a good partner to sales. That goal was a 2020 goal, it will be a 2021 goal, and it’ll always be a goal for us.

In FinTech, the beauty of the evolution is new use cases would come up every single day and every single week. A lot of inbound interest comes to us with use cases even we don’t think of. The goal for marketing is to help discover those use cases, help figure out what the potential and possibility is with those use cases, work with sales to close the loop, and make sure that we are ready and defining the category around all of these use cases. Startups innovate and companies are building out all of these use cases. In fact, ranging from the largest banks all the way to the smallest FinTechs, everyone is thinking in a unique way. As someone that provides the infrastructure for a lot of this evolution, our goal is to be ready for it. As we go forward, the goal for marketing is to become better at evaluating and anticipating, and then be a partner that is more true at the top of the funnel than who we are now. That’s an ongoing pursuit as well.

Is it your team or is it in combination with product marketing or some of the functions that you identify all these use cases?

It’s all of us together. Partly it is because we only have so many people and we don’t have the luxury of having 50% of agencies that can do the research for us. We are this crappy organization. There are some other aspects to it. Sales team gets the most exposure to all these upcoming teams. We have to leverage them and they have to leverage us for making sure that all the execution and positioning is in place. That exploration within sales and marketing at the top of the funnel, those two pieces are very important. Beyond that, it happened at every single level. For a marketer who is a startup at this point in time, our exec team will come up with referrals and use cases. Our board will send things done our way and say, “I have this portfolio company that is trying something.” We get exposed to this innovation from many different angles and our goal is to be effective at responding to it.

I’m extrapolating and continuing the discussion on the 2021 piece. If you were given an X-number of dollars, where would you channel that? Would it be more on the OPIC side or more than a headcount, or is it a combination of those?

B2B 8 | Go-To-Market
Go-To-Market: Don’t think about something as a big strategic objective; rather, think of small wins and how, when combined together, they get to the final outcome.


Headcount would likely have much more impact than necessarily OPIC’s. That is also because we don’t have a very massive universe of decision-makers that we are going after. We are looking to engage with payments professionals that are working on transaction volumes at scale. These professionals are becoming more and more common across many different companies. Even your classic tech company now is starting to have payments professionals to automate, whether it’s their internal corporate expenses or any of the use case within. First of all, payment is becoming more common but broadly speaking, the universe of decision-makers that they’re going after is not that massive. There’s not so much for us a money game in the outside online paid work. What it is for us is, do we have the right content that we can put in front of these prospects as they’re exploring?

Content is a big objective, especially in FinTech, the better the content can be in terms of quality in terms of its ability to explain our business to our prospects, the better suited we are. Content is a big priority if we’re given more resources. The other piece, as we think of customer-centricity, if I were to look at scaling up, I would look at ways and means to get insights out of customer product use, scale, retention levels to get that intelligence to be a feeder into the marketing thought process. That would be the second objective. Beyond that, marketers are scaling across all facets. The more we keep doing what we are doing, we’ll still continue to get returns. It’s not like we are anywhere close to getting diminishing returns for anything. The more we invest, the better we are going to do with marketing.

It’s not surprising you say that content is a big challenge. Who I spoken with like the different CMOS and even the VP of Marketing at different organizations so far continue to say, it’s content. If I have to bubble it down, especially around the notion of, “Am I understanding my buyer and the user well enough?” Again, it goes back to not having the bias. Going back to a startup world where you don’t have the internal bias but then truly and out of curiosity, you’re trying to understand the problems of your buyer and the user. If you package all of that into content, that’s the key.

That mindset and skillset is extremely hard in the tech industry. That’s a recurring and resonating theme that I’m seeing across in the tech space. I have some pointers and guidelines as to what I’ll be sharing with my clients. That’s something that I can do offline. We’re coming up on time, so going into closing section over here, if you were to look outside in the industry across the B2B SaaS space, Salesforce, or other industries are hurting in the Startup world, who would you give a shout out to those 2 or 3 whoever leaders from go-to-market perspective who are thinking and executing very well?

Generally, I’ve been very fortunate to have been a part of Salesforce for such a long time. To be extremely honest, marketing is a first-class citizen in a large company. There are lots of large companies in the B2B world where overtime, marketing gets relegated into second-class citizenship a little bit. In many situations, sales become more and more powerful and then it starts becoming a one-way path a little bit more. The innovation died away but at Salesforce, that’s not the case. Lots of execs at Salesforce and everyone that I’ve had a chance to engage with have been accomplished and impactful on their own. I was lucky in that as someone that initially started their time at marketing doing business planning. I was a little bit on the buy-side.

I was able to ask questions to every single entity within marketing at Salesforce, if not to understand then to probe. Over time, there’s been a lot of friendships that have been built. A number of them are CMOs. CMO at Marqeta, Vidya Peters is from MuleSoft but now that’s a part of Salesforce. She’s been a highly impactful leader at Marqeta. I wouldn’t want to not name anyone but if you think of any exec Salesforce now, a number of them have been there for a long period of time. They’ve been inspiring on their own right. For me, it’s more of a shout out to that ecosystem. I’d say more of a shout out to the fact that they have been able to be so impactful for such a period of time. It’s helping out the entire tech ecosystem with all that they’re doing there.

Well said, Ajit. I completely agree with you. Salesforce is one of the few large organizations where marketing is a first-class citizen in your own words. It’s part of the DNA and it comes from the founder. If you look at Marc Benioff, he’s completely a marketing and a sales visionary and that trickled stone. Salesforce overall has been fortunate to have that whole thing and is still embedded in the DNA. The final question that I have for you is, if you were to rewind time and go back to the early days when you started in a go-to-market function, what advice would you have or what advice would you give to that person?

Let me make a couple of comments and then I’ll get to that piece. When I started at Salesforce back from my time at Opus Capital then I transitioned from venture capital into marketing, my whole thought process was someone that is smart can come in into marketing, look at the entire landscape, use hopefully, first principles driven approach, can understand the problem, solve the problem, and optimize the situation. That was the thought process that I came up with. Years later, when I left, I was nowhere close to having a solution to any of this. There’s one learning here which is to understand that go-to-market broadly, even something that is as black and white as sales is still an art form.

It is as good as what you make of it. It is as good as the effort that each individual in that organization puts in. The goal for a go-to-market lead or even a contributor needs to augment their strengths in pursuit of product-market fit for their company. That’s one advice. The other advice that I would give to myself, which I aligned to that shortly after was simplicity wins as complex as you can think, marketing, sales, or any of these things might be. The simplicity piece is what rules every day. Do you believe in your product?

As complex as you can think marketing might be, simplicity wins. Click To Tweet

Do you think your product is a winner? If it is, then figure out how best to showcase it in the right way. Keep it simple, keep it to the point, and think of it from the perspective of the other party. The other party understands less about your product than you do by default then bring it down to the level that they will understand it. If there is a need with your thought process, they will become customers. To the extent that they are customers and you continue to keep them happy, they will become your evangelists. That’s what it boils down to.

I think of those two words. The words that summarize everything are simplicity and empathy. That’s what I would say as well. Well said, Ajit. Thank you for a wonderful conversation. It was a pleasure to have you on the B2B Go-To-Market Leaders Podcast and good luck to you, Ajit, and to your team at Marqeta.

Same to you, Vijay.


Important Links


About Ajit Deshpande

Vice President of Demand Generation at Marqeta, Inc





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B2B 7 | Building Empathy

B2B 7 | Building Empathy


Allowing your customers to understand where you are coming from and how they can personally relate to what you have to offer is the best way to build the go-to-market. By building empathy with your audience, you’re on the right track towards starting a successful connection. Joining Vijay Damojipurapu is Charlie Wilson, Chief Revenue Officer of cannabis provider Greenbits. Together, they discuss how to maximize human interaction to achieve an unparalleled customer experience, as well as the importance of well-targeted product manager-marketer collaboration. Charlie also talks about the most crucial marketing points every start-up business must know, especially in this time of pandemic and with the go-to-market gradually becoming an independent function.

Listen to the podcast here


The Power Of Building Empathy In The Go-To-Market With Charlie Wilson

I have my friend and someone I look up to from a go-to-market perspective. His name is Charlie Wilson. He is the Chief Revenue Officer at an upcoming and high-profile startup in the legal cannabis space named Greenbits. Charlie, I’m turning it over to you. Welcome. How are you doing?

Thanks, Vijay. I appreciate the kind words and it’s great to connect.

As always, I start off with asking the first question. My significant question is what the show is all about, which is how do you define go-to-market?

At the end of the day, it’s about putting together a bundle in an approach to create brands, both perceived and real. Making sure that you’ve got the right audience and you’re ultimately delivering an experience that’s well-coordinated from the internal perspective so that it’s experienced and perceived that way from the external perspective. At the core, that’s what it’s all about.

There are a lot of moving pieces below that to make it happen. It’s not about what we in the company see from either a product or a services perspective, but how all of this ties back to the customer, the buyer and the user.

Your success in go-to-market is going to be a function of having to find those things well and coordinated those things well internally, which is why I really orient around that, as opposed to more an outward-looking perspective than an inward-looking perspective.

I’ve been speaking with my clients as well as several other guests. It’s always a combination. It’s not easy where you always constantly need to have your eye on the market on the external perspective. At the same time, you need to be grounded in reality and grounded in perspective as to what can we deliver and still be sincere as a company and a brand when we’re looking to deliver value to the customer in the market. Let’s dive a bit back, let’s rewind a bit. Let’s talk about your evolution as a Chief Revenue Officer. How did you start your career and what led you to actually take this role and go down this path?

Never allow yourself to be stuck in just a single role or field forever. Click To Tweet

It’s a story journey. I was an engineer as an undergraduate and graduate student. I had a focus on technical skills but early in my career, I never practiced pure engineering. I was in management consulting, so I had a broad base of experience. I joined the strategy group at Visa and a large organization. I had an opportunity to see a diversity of things. Through those experiences, I got interested in sales and marketing side of the equation. I never would have considered myself a salesperson or marketer in my early days.

I came to value and appreciate obviously the importance of those parts of the business and the relevance of those parts of the business. I started to cut my teeth in some sales roles, increasingly marketing roles and have evolved down that journey for the last several years. Most of my career has also been industry-wise and FinTech. My journey to Greenbits in particular wasn’t so much cannabis-driven, it was more of a business model-driven in terms of understanding that SaaS and FinTech intersection and seeing the opportunity within this particular vertical, which as you can imagine firsthand, it’s unique and evolutionary or evolving continuously.

Quite a few things that I want to double click in what you shared. It’s definitely a good journey. This is something that I keep reminding to several folks that I meet with as well as to the audience. Nuggets and lessons for the audience is you don’t need to be feeling stuck in a specific role or a specific field. You mentioned about you started off as an engineer but never saw yourself growing in that role and that’s where you start exploring and going down the path of more on the business side but more on the marketing and imagery to the sales and not the revenue ownership piece. I think that’s one piece. I am curious if I double click on that. What really attracted you or pulled you away from engineering towards more on the business side, starting with the marketing piece?

One, it’s a general interest and fascination with characterizing the business world. I think the technical background provides some important underpinnings that in this day and age are table stakes that many years ago were probably perceived as luxury. I don’t think sales and marketing disciplines historically were as data-driven as analytically focused. Clearly, for the last several years, they have become that way. Having that foundation and leveraging that foundation in the area where candidly I’d probably had more interest in the marketing side and the sales side. Being able to break down the market, segment that market, understand where you can set yourself apart, differentiate yourself, ultimately bring somebody through a buying journey and to a close sale. Seeing the enjoyment of that dynamic with both enterprise customers, which are a different beast, as well as small businesses and tailoring the go-to-market experience based on some of those customer profile dynamics.

I was looking forward to and wanting to push you on that piece, which is, I know you’re big on the small customer piece or the small customer segment. Early on in your career, you started off with customers and markets that are more enterprise-focused but somewhere along the line, you got pulled towards serving the small to medium businesses and the retailer. Tell that story. I want the audience to take away from that as well.

I was at Visa in my early days. Visa’s client-based are banks. Many of those banks are large. Those types of conversations and deals are more enterprise. In subsequent roles, I was still in an enterprise context. Probably the biggest thing that attracted me to small businesses was when I met my wife who happens to be a retail small business owner. I didn’t grow up in a family of small business owners but upon meeting my wife, I saw some of the trials and tribulations that a small business owner goes through. Small businesses in particular, they usually get into their business because of their craft and their passion, not because they like to do payroll or taxes or all the other things that are associated with running a small business.

It was also synonymous as my own career progressed, you had the opportunity to serve small businesses. They’re incredibly on and underserved. They’re incredibly difficult to serve. It’s a fun challenge from this side of the table. It’s what led me for probably the last few years to have a focus and an emphasis on delivering great products and experiences and getting those into the hands of small businesses, particularly a mom and pop-like stores. That’s true in our industry. We work with a lot of characterized enterprise, probably a stretch to mid-market like businesses in a traditional context but also a lot of new to retail, single-store operators. Pursuing a passion, a dream in cannabis and chasing that opportunity. We get the opportunity to bring them a suite of services that makes their lives hum a little bit easier.

B2B 7 | Building Empathy
Building Empathy: Small businesses usually start with the owner’s passion and not because they love to pay their taxes or do payroll.


First of all, from your personal experience, you actually can connect with that target persona or the buyer. I think that’s key for anyone in product marketing, sales and even to that extent of customer success. You need to have that empathy piece. From your story, it was clear that in your case, your wife, as a small business owner, you could see the tribulation that she is going through and she went through. You’re bringing that empathy piece to your current role, which is essentially helping Greenbits build a point of sale or compliance and the various other technologies. As you’re selling to the legal cannabis retailers, who are mostly small to mid-market as of now, that’s the majority of the market. That’s the key. The point I want to hit is the empathy piece and nothing like building empathy from your own personal experience.

It’s understood but I think it’s still often missed. You’ve got a lot of smart people who have good ideas, they can build great technology, can analyze and break down a market but I think a lot of times, businesses and groups miss the mark in terms of that true empathy and true understanding of the experience that the recipient on the other side is experiencing. We still struggle with this and work to improve this. You have to put yourself in the shoes of the person on the other side. When you think about a small business owner in particular, the breadth of things they have to deal with, in many cases, they are the sales organization, the CEO and the human resources departments. They play a lot of hats.

A lot of times they’re in that situation because they have a passion for baking cupcakes, for instance, or mountain biking and selling retail mountain bike parts in a retail environment. Not because they like to do those other things and often, they’re underwater and those other things. If you understand that, you appreciate that and you incorporate all those other distractions and stresses that are on those businesses, you can be more effective in positioning and getting your product or service to that audience that’s very underserved because they’ve typically been difficult to serve, historically.

Building on that point of empathy, which is very crucial in the whole go-to-market piece. Personally, from my own experience, I’ve had the good fortune and been grateful for all the several product marketing or even head of marketing roles. In that capacity, as a head of marketing, my responsibility and you have the company-wide customer, which is the market segment but the internal customer is sales. Sales is the number one customer for the marketing team and something that I’ve realized after I’ve started the company that I’m running, Stratyve, which is serving or helping essentially the B2B SaaS companies build go-to-market either clarity or go-to-market efficiency.

I’m playing and wearing multiple hats or roles and at the same time, I’m actually wearing the role of a salesperson. Ever since I’ve embarked on this journey, where I need to do the outbound or I need to do prospecting. I need to help understand the buyer from their pain points and their challenges was this internal from me, “How do I close the sale?” That’s an entirely different mindset. Personally, again, going back to the meta point that we’ve been talking about, which is building empathy and nothing like having a personal experience to build that empathy piece.

I think something that has impressed upon me, the more I’ve progressed through my career, that domain experience and that firsthand experience is critical. I think of myself and lots of people can go into an environment that they’re unfamiliar with and be successful, but I will tell you to have that domain experience to have the firsthand experience is valuable. Not to say that it can’t be overcome but it goes a long way in establishing that empathy and unlocking or uncovering, or at least being aware of some of those intangible elements to be successful in serving a particular segment or audience or individual.

In your role as a Chief Revenue Officer, you have the complete visibility into what the marketing team is and should be doing as well as the sales team is and should be doing. You got that end-to-end perspective. I want to hear from you as to how you create that alignment and empathy piece, not between the two or across those two functions but even with the whole buyers in the market.

There is nothing like building empathy from your personal experiences. Click To Tweet

It’s not rocket science but data-driven, clear and concise communication. Those things allow you to make sound decisions around where you put your energy and they allow you to execute effectively. Much of the working world is about the human interaction and to the degree that you’ve got sound communication between those organizations, you’ve got a common understanding between those organizations and others. You can be at a heck of a lot more effective. I think where things break down or where they succeed, it’s less about the specific disciplines of marketing or sales per se. It’s more about common sense and foundational things like structured communication and effectiveness there. There’s always going to be a good tension between sales and marketing in terms of where one ends and the other begins.

We try to impress upon our team and our organizations that there’s not a black and white line or a clear line. There’s a very healthy overlap. You used the term empathy. The more that the marketing team is empathetic to the experience and what the sales organization is going through, the more effective they can be in assisting or helping in that respect. Conversely, the more empathetic the sales organization get to the things that the marketing organization is trying to take on. You see some companies, particularly startups, there’s a notion like, “Everybody in the company does a role in customer support,” because you build empathy for the customer. The more the sales organization can spend time and live the life, so to speak, and the day of the marketing organization and vice versa, the more the marketing organization can live a day in the life of the sales organization. I think the more effective they can be individually and certainly collectively. It’s never easy to get that quite right but that’s what we strive for.

I want to get your thoughts. There is a growing notion around the whole revenue team which comprises both the marketing and the sales, but there’s also the whole new field of revenue ops. I want to get your thoughts on those.

We actually have a role open for a revenue ops individual. Historically, I think we probably looked a little bit more like other businesses are certainly where the trend or the precedent was before we had sales ops and marketing ops. I talked about the empathy and the communications but the other piece I talked about was the analytics and the data. The degree that you have somebody in the revenue opposite role, you’ve got somebody in the interstitial space between sales, marketing and arguably customer success. The by-product of that is you get data and analysis and insights in an unbiased and independent fashion. You’re not getting the skew or the biases that maybe the marketing organization or marketing ops person might put on a situation or conversely the sales ops.

You’ve got somebody who is sitting in that interstitial space to make sure that the organization at large is getting the most relevant information and guiding and the most appropriate sound direction. You remove some of the silos. You remove some of the biases and some of the potential areas of tension by looking at that across those functions, as opposed to within those individual functions. We’ve embraced that and have adopted that end of the process of continuing to expand that.

This is something that’s been playing on my mind especially when it comes to the go-to-market. This show is all about go-to-market. Even the work that I do of Stratyve is all about go-to-market. If I tie it back to the experiences that I’ve had previously when I was working at other companies, it was mostly around product marketing, “owning go-to-market.” If you’d be in the shoes of a product marketer, it’s extremely challenging. Product marketing can come up with a good market strategy but to execute and make things happen both within the broader marketing organization, as well as with the sales organization is extremely tough. It’s not within the scope of that role. That’s something that’s been playing on my mind and seeing the trend playing out in the industry, which is the go-to-market piece is slowly beginning to come out of product marketing. It’s more of an independent function, more of an independent team on a role that’s sitting across and outside of marketing sales or even customer success to that matter.

I would extend that and in my mind, two of them are the most influential individuals in the organization, depending on your designer and depending on obviously the industry and who you’re serving are the product manager and the product marketer. Those two individuals and those two roles are at the center of the universe. To your point, they’ve got to drive, coordinate and organize a lot of different individuals and functions in order to be successful. We look at it the same way. That product marketing role is critical, particularly in our industry where finite universe of operators and a lot of word of mouth. The ability to clearly convey the benefits and the products and create great experiences within the product and the service is critical to our overall sales and marketing success. In our particular industry, I would say those roles are even more amplified than they may be elsewhere.

Going back to the whole rev ops role, I’ve also seen the rev ops role reporting possibly into the CFO organization as well. The CRO/ CFO is a dotted line because at the end of the day, it’s about alignment but at the same time, that role has to stay true to, “I’ll be hitting the numbers. I’ll be hitting the metrics that we need to hit as an organization.”

That’s fairly similar within our organization. Particularly on the analytics side, you want the finance organization to be close and then again, very consistent in terms of understanding the data, the sources of data and what the data is explaining or telling us. My organization, which is not a finance organization but there are a very close collaboration and a very keen interest from the finance organization in terms of those insights, knowledge and those experiences.

Switching gears a bit over here. Essentially, we highlighted or talked about how you as a Chief Revenue Officer of Greenbits, come up with maybe the 2 to 3 key go-to-market programs. How do you think about it from an annual goals perspective as well as break it down into quarterly goals to a functional individual? Sharing that piece will be insightful for the readers here.

I’m a big believer in usually fewer is better and simplicity is better.

B2B 7 | Building Empathy
Building Empathy: Being data-driven and having clear communication allow you to make sound decisions on where you should put your energy.


It’s extremely hard to do it. The reason being is the shiny thing syndrome, as well as they say the fear of missing out. This whole matrix is playing out there.

In a startup, oftentimes you have to do many things. I think you have to be incredibly focused on what’s critical. If I go from the long horizon to increasingly shorter horizons, when we map out the annual priorities, we try to focus on a small number of critical initiatives and basically, work your way back. I personally like to break things down into 90-day periods. It’s enough time where you can make tangible progress and have the freedom to be able to demonstrate and make that progress but it’s also not so long that you run the risk of getting too far off course. Backing down from those 90-day periods of those three-month periods, you’re starting to further decompose the objectives and meeting that annual target or goal by the individuals or the groups themselves.

I think that the criticality you get what you measure and what you had said, it’s important that you’re measuring things that don’t create a red herring. An MQL is only as good as the quality and the integrity of the definition of that MQL, for example. Making sure that you’ve got not only the right metrics but the right definitions behind those metrics to make sure they’re unfortunate drive in the right behaviors to ultimately hit those annual and multi-year objectives.

If I have to extrapolate on what you mentioned here, you’ve got their annual objectives around the revenue numbers, the sales booking numbers, the pipeline metrics. When it comes to marketing, you got MQL piece but then there’s also the inbound traffic, outbound campaigns and so on. Tying all of these into the various initiatives that marketing and sales have to do for the next 3, 6, 9 months. I think that’s critical.

We generate deals from both outbound activity as well as inbound activity. Making sure that we get the right mix and the right balance there for our business and where we can be uniquely differentiated and competitive.

In doing all these things, how are you thinking about the big initiatives for 2021? I have a follow-up question after that, but let me stop here. How are you seeing 2021 for your organization?

We socialize this with our board. We’ve gone through a planning exercise for the year ahead. As a company, we’ve got four priority initiatives over the course of the next year. Two of them are initiatives that are new to us. There will be a big element of go-to-market relevance in the year ahead and our ability to execute effectively will be critical to our success but again try to maintain a finite number. We make sure that we were focusing on the things that we can get the greatest leverage from that can most substantially move the needle, advance our business forward, advance our customer’s success in the most profound ways over the course of 2021. Some of them pertain to new geographies, new products and services that we want to attach and introduce to our customer base.

The follow-up question I had is what do you see are the big challenges? You did mention about go-to-market as a big piece for 2021. What do you see are the key challenges?

It’s the coordination across the organization. I’m fairly confident that we’ve got the segmentation right. We can figure out where to identify these people, get the right messages in front of these individuals. It’s ultimately bringing those things together in unison where the messages get to the right people the right times, the execution of the product development hits the market the right point in time and lines up nicely with all of that. It’s not too dissimilar than what I think people experience in any other business or service offering a product or a service offering.

I was actually in conversations with a couple of my clients as well as with some of the guests who are CMOs and VPs of marketing and to share with you, Charlie, a couple of things that are top of mind. One thing is around, 2020 has been a challenging year from a COVID perspective but at the same time, all of these marketing leaders have been and are still very proud in how they have had the team pull together and still execute. Maintain that focus and still execute from an operational perspective, a mental health perspective and being dialed in perspective. One challenge that comes up is, “Now that I’ve done that for 2020, how do we do that with 2021 without being too diluted or being fatigued by this whole notion?”

I am proud and I applaud our team for 2020 now. I would say 2020 has had its challenges. For our particular industry, we’ve been fortunate. Our businesses thrived. I think our customers’ businesses have thrived and have been in a position where they’ve been able to operate and they’ve been able to continue to grow and expand. There have been hiccups, nonetheless. 2020, looking back, was a successful year. I think the team did a great job with lots of fluidity, uncertainty and challenges. An interaction like this where everything has gone to remote. I think technology companies and our teams are generally well-suited to make that natural transition to a fully remote work environment but there was transition and change and adjustment nonetheless. The ability to have the in-person interactions, collaboration, that’s been null and void which has made things difficult.

The go-to-market piece is slowly beginning to come out of product marketing and become more of an independent function. Click To Tweet

The part that’s been most challenging is the ability to have those interactions with customers, whether it be in the sales and marketing experience or with existing customers. That’s been the part that’s probably most challenging. I’d say going into 2021, we feel good. There’s some momentum that we need to maintain. There’s fatigue but I’d characterize our fatigue is the fatigue of the startup, not so much 2020 derived. Personally and myself, I’m very optimistic about 2021. I feel very fortunate around 2020 and take that we’ve actually got momentum behind us as we go into 2021 where I recognize some businesses are probably feeling like they’re having to dig themselves out. Fortunately, we’re not as subject to that as some.

Double-clicking on that. Your customers and the market use of the legal cannabis retailers. From an outsider perspective, I’m assuming that clearly their businesses would have been hit but at the same time, not getting too much into detail of why cannabis sales would take off. I want to get your thoughts on and your view on how the industry overall has been affected or not been affected. I want to get your perspective on that.

When COVID showed up in mid-March 2020, most of the United States and businesses in the United States had a tremendous amount of uncertainty and that was true with our industry. Fortunately, cannabis is not a federally illegal market, it’s a state legal market. You have a very fragmented market state by state rules and regulations. In our industry, for all intents and purposes, nearly every state with the exception of one deemed dispensary and deemed the cannabis industry as an essential business. They were able to stay open during those March, April, May months. The other dynamic is when you had a lot of people home probably stressed out, to some degree bored, anxious and a lot of real and understandable reasons.

Our operators not only remained open, they actually thrived in a lot of respect. Our customers, we’re fortunate through that process. There were lots of regulatory adjustments and emergency regulatory rules that people had to accommodate with curbside. Imagine our industry has cannabis plant involved and it’s a heavily cash-intensive industry. A by-product of that, as you think about, “Curbside pickup.” There are a lot of logistical challenges that come along with that dynamic when you’ve got a lot of cash and cannabis products outside the four walls of the store. Our operators had to accommodate and adjust to certain things for our customers. Fortunately, they were in a position where at least they had the opportunity to make those accommodations where a lot of other industries were purely shut down.

There were some things that were delayed. New businesses that were going through final inspections. Some of that got delayed. States and industries like Nevada, particularly Las Vegas, very tourism-driven segment of geography. Not a lot of tourism happening in Las Vegas. We saw operators there struggle certainly for a period but by and large, our industry has been fortunate. Our customers have had to deal with the fluidity that COVID has presented but fortunately, they’ve been open for business. In fact, we’ve seen record numbers during the balance of 2020. We’re hopeful and optimistic that that carries forward into 2021. In fact, you see the election, the general industry, our particular industry, we had five more states legalize through this latest election. We feel excited and confident.

Definitely exciting times for the industry as well as the players in the industry. I can see that happening. As we wind down a bit last couple of questions here, Charlie. You did mention about some of the goals for the big initiatives for 2021, as well as some of the challenges that you foresee. You mentioned about rev ops as being one of the key hires or somewhere you’re going to channel some more budget into. Can you expand a bit upon that aspect based on the go-to-market initiatives, what do you see as the key hires? If you had the extra budget, where would you put that extra money into?

B2B 7 | Building Empathy
Building Empathy: If the marketing team is empathetic to the experiences of the sales organization, they can be more effective in assisting them.


Prudent capital allocation is critical. We have much more opportunity than we do. Resources are at our disposal. There are a few different areas. I think the ability to expand our available market a little bit more quickly. It’s fragmented in the United States state-by-state and there are some nuances to the way that our industry, product and service works, where we have to be a little bit more methodical. We can’t blanket all states at once. There’s a vibrant federal illegal opportunity up in Canada. There are always areas where we could expand geographically faster. The product we’re a relatively new industry in a relatively new company.

In the grand scheme, your product and service offerings are still relatively immature. We’re in the early innings, we got a long way to go, so we can accelerate some of those capabilities that allow us to deliver more functionality to our customers. Drive price points and average revenue per account higher would be areas that we would look at. I think one that we’ve had in the back of our mind that if I could carve out a big piece would be on data and insights. There’s not a lot of knowledge around this industry. We have visibility and sit on a ton of data that I think we can package up in service to our customers with new insights and capabilities. That’s probably an area where if I had some additional resource and budget would carve out a new and distinct and separate initiative to go after that.

Expand on the data and insights piece.

You have emerging brands. You have CPG companies around various form factors. Infused beverages and edible products and bulk flour and pre-rolled joints, oils and tinctures. You’ve got form factors that manufacturers are trying to understand where consumer preferences. You’ve got a lot of new to the industry consumers. Either people that may be coming back to the industry, people that have never experienced the industry. There’s a ton of education on the consumer side. You can imagine the brand and the product companies are trying to figure out like, “What are the consumer trends and buying behaviors and patterns that inform their own product developments?” You’ve got dispensaries and retailers that are trying to establish their brand, build their own awareness, drive foot traffic into their stores and properties. Given that we sit on a large body of data that looks across that continuum, we think we can provide a lot of valuable services to our retail customers, as well as the brand companies, many of which are our retail customers as their vertically integrated businesses.

Data and insights and data signs and the whole notion. I think that’s a big thing from a go-to-market perspective especially. There’s going to be a continuous demand for the whole data science personnel and people with that skills. At the same time, the key is not the ability to run the data models but teasing out the insights and then channeling and coming up with the key go-to-market initiatives for marketing sales or even customer success. I think that’s key.

Leveraging that to inform where we go as well.

It’s great conversation, Charlie. I think you shared a lot of nuggets and advice for the readers as well as for your peers in the industry.

I appreciate it.

Last two questions. The first one in that bucket is if you were to look outside and across your shoulder in the industry overall, who would you call out or who do you give a shout-out to as someone who’s doing a great job from go-to-market perspective?

Our model is similar to some of the commerce models. The world of companies like Shopify and Square are two companies that have done a phenomenal job around understanding their market and communicating effectively to their target audiences. Building their product and service often and creating a comprehensive experience that is meeting the needs of their particular audiences, which both happened to be generally small business segments as well. We’re doing it in a vertical context but I have a ton of respect for the individuals within those businesses. The way that those businesses have generally operated from their early days to where they’re at now are incredibly prosperous and market-leading businesses.

In order to grow, soak up information anywhere and everywhere you can find it. Click To Tweet

One final question before I let you go. If you have to rewind the time and go back to not your eighteen-year-old self but if you have to go back to your first day of venue to go-to-market role within marketing, most likely it looks like out of your engineering into the marketing team. If you have to go back, what advice would you give to that younger self?

I would say soak up information from anywhere and everywhere that you can get it. There are lots of nuggets of good ideas and new and different ways of doing things and a lot of unexpected places. The other thing and these are things that I embraced through that period, but I would reinforce it and probably try to amplify it. These things we talked about, understanding of empathy, a broader understanding that you can then dry in and create more narrow and targeted focus, breadth of reading. There are some people who read a lot of business books and there are some people who may read no business books.

I like to have a diversity of reading and try to consume as much as I possibly can. I would say too as much of that as you can because I think as you draw in these various pieces of knowledge that we’re in a world, that’s soundbite driven, very Apple news-driven. I try to abstain and I would encourage people to abstain from those little short snippets and actually read books. That’s where you get more complete thoughts. You get more diverse and interesting insights that make you a more complete person and that more complete person can deliver a better experience of whatever you’re doing, whatever you’re doing whether it be a marketing or go-to-market role or any other role. I think some of that is lost on society at large and certainly is lost on the younger generation because candidly of what they’ve been fed. I think that’s important. I’m reading Thinking, Fast and Slow as my latest book and next I’ll probably pick up a novel, whatever that might look like.

That’s a great piece of advice and a great note to end on. Reading and carving out the time to read every day or at least a couple of times a week. I think that’s important. I personally experienced a lot of growth. From that growth and insights, I’m seeing that on how it’s helping me shape my thinking and how I can help my customers better. That’s a key point there. Thank you for your time, Charlie. You’ve done a great service. Sharing your insights, advice and nuggets to the readers. Thank you for being on the show.

It’s my pleasure. Same to you, I appreciate what you’re doing and great service. It’s great to connect. Thank you.


Important Links


About Charlie Wilson

B2B 7 | Building EmpathyProven leader with a mind for the big picture and an eye for the details. Twenty years of executive experience with pioneering technology, payments, and commerce companies. A natural networker, a quick study, and strong advocate of payment solutions for cannabis retail. Earned two engineering degrees: B.S., Arizona State University; M.s., Stanford University.



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B2B 6 | Lead Scoring

B2B 6 | Lead Scoring


Lead scoring is a vital element that sits at the intersection between marketing and sales. It’s something that companies need to think about from an early stage. It is a simple idea but it is often so poorly implemented that it doesn’t produce a lot of the results it is designed to produce. Breadcrumbs attempts to address the fundamental flaws of this process through a simple interface where people can design their own lead-scoring model within a matter of minutes. The company is the latest among several startups founded by Armando Biondi, the former COO of the digital marketing platform, AdEspresso. An active member of the startup ecosystem since 2009, Armando has a depth of knowledge and experience when it comes to go-to-market challenges and strategies. He articulates some of these in this conversation with Vijay Damojipurapu, where he also shares the story of AdEspresso and the recent work he and his team are doing at Breadcrumbs.

Listen to the podcast here


Breadcrumbs: Scoring Leads The Way It Should Be Done With Armando Biondi

I have with me, Armando Biondi. I’m super excited. I’ll run through the background of you and all the great startup journey that you had. Welcome to the show.

Thank you for having me.

I looked at your bio. The reason I was excited and looking forward to having you on the show is a couple of reasons. One is around the breadth and depth of experience, having done either the C-Suite roles, the founder roles or even a board member role in six or even more startups. You have the depth that is needed for the go-to-market and the breadth. The second reason is you have been, and you continue to be, an active member in the whole startup community and startup ecosystem. You are an Angel investor, so that’s a big deal. You are also a mentor and a board member. You’re not seeing the go-to-market challenges from the companies that you’re working at, but you’re seeing it across the entire startup ecosystem, maybe tens or even hundreds of startups. I’m excited about that. Let’s start off with the most obvious and the signature question for the show, which is, what is your definition of go-to-market?

The way I think about go-to-market is the all-encompassing definition. Meaning, everything that has to deal with how you bring to market a product or service or the combination of the two. There are marketing, price, and packaging element around it. There is a service or a support element around it to some degree as well like how you fulfill the promise of it, how you commit to that promise and the mechanics behind it, so there is an element to it. Those are the main categories that come to mind when I think about the go-to-market.

Double-clicking or diving in from a go-to-market perspective for an early-stage company or a product will be different from the go-to-market for a more mature product. The flavor of go-to-market for a product line versus go-to-market for a company, it’s entirely different. I’m curious about your thoughts on those.

This is already a potentially big topic meaning that if you want to summarize it relatively quickly and up to you how much time you want to spend.

We have plenty of time. No worries about that.

If I think about the go-to-market from a startup perspective or at least stage company, the reality is that the vast majority of people tend to overthink things. If you think about successful companies out there at an early stage or successful exits up to $5 million to $10 million ARR or revenue if you’re thinking about the SaaS world, the idea is that most of those companies need to nail one go-to-market strategy/back. They don’t need too many on top of that. If you accept that thought, one of the things that you see over and over again is founders being constantly in search mode.

Not realizing per se that they stumbled upon something that is working so continuing to look for other things without doubling down on the stuff that’s working now and that can continue to work up to a certain point. These can come in flavors. It can come through an inbound, content, outbound or paid even for the B2C company that we’re talking about. The reality is that most of the budget and funding that any B2C company would raise through pay. You have to nail one go-to-market strategy to be successful or even lead to many more.

Being your first customer helps a lot because you gain a lot of insights into what's working, what's not, and what people like you need. Click To Tweet

That will progressively change as the company matures and grows because at some point if there is one thing, which is always true about go-to-market strategies, is that there is a ceiling. They start to work less effectively or not as well as they were before. You exhaust that potential and you need to look for additional sources of growth. That is when you start expanding into multiple go-to-market strategies that you keep executing on in parallel and you have working in concert with each other and to drive growth.

Usually, what happens as well is that companies tend to move from high-performing, highly measurable type of tactics/strategies. If we’re talking about advertising DR, direct response-type of motion and as they evolve and they start topping out that channel, they start migrating towards the less performing and less DR type of channels. It’s more brand-related and intangible and then layer all the different strategies on top of each other. That’s very common when you’re thinking about these types of companies in motion.

That’s a good summary. That’s the last topic. We can pick and do an entire episode on that one question, but we have a lot of ground to cover over here. Switching gears a bit, I did a quick research and looked at your profile in how you grew up the ranks. You started out as an employee first and then went up to the VP of the C-Suite level and then somewhere along the way, the whole startup bug caught you. You’re done Pick1 and then the Batch 5 & 7 then, of course, AdEspresso, but now we’re talking about big names. AdEspresso got acquired by Hootsuite and then now you’re at MailUp. I’ll also let you share the new thing that you have on your mind. Walk me and the audience on how you grew from the ranks of “employee” to switching on going into the inside.

That realization is that I generally have always been a very bad employee. I’m not an employable person. The reason for that is I tend to get excited about hard stuff or hard things. I constantly challenge myself. As a consequence, I tend to ask a lot of the people around me as well. I am the most excited when I can participate in the upside of the value that I’m contributing and creating. The reality is that the employee world is not built for that. What you’re trading off when being an employee or when you’re making the decision, consciously or unconsciously, is creating security for the upside.

When you’re an employee, you have a series of guarantees, stability, paycheck, benefits and all that good stuff. To some degree, that takes away a little bit of the upside that you can get. You’re accepting that the upside is going to be captured by your employer. When I started realizing those things inside my head, I said, “It’s time to try this entrepreneurial thing.” I started my first company which was Pick1. I started my second one, which was social market research for enterprise companies based on Facebook. Based on that experience, they don’t go super far. We ended up selling that. It was a good outcome. It’s not a lot of money, but it’s great learning. As a consequence of that, I started AdEspresso realizing that Facebook cared more about the advertising side as opposed to the research side and was willing to produce data, but not keep data away.

AdEspresso is essentially Facebook advertising and split testing for medium businesses as medium enterprises. At the time, Facebook split testing wasn’t the thing. They ended up taking “inspiration” from many of the ideas that we had implemented in the product. As a company, we ended up growing very aggressively in three years from 0 to 50 people for about $6 million in ARR and about $300 million in Facebook advertising budget process through the platform on a yearly basis.

AdEspresso is one of the top five ad tech partners for Facebook globally and the number one by a number of advertisers because every ad partner was focusing on a small number of big advertisers while we were doing the opposite number of small ones. That led us to the relationship with Hootsuite and we ended up selling it to Hootsuite, which was an acquisition that made a lot of sense back in the days because social media management solutions out there on one side were the biggest mid-market, Facebook advertising partner on the other side. Through that experience and then stayed on with Hootsuite as a global head of growth operations, overseeing ads products within the portfolio as well as the ads that we showed up growing about 3X since then.

There are a couple of realizations. One, the laws for speed and growth to the obsession of not only growth but also efficient growth. You can spend a lot of money to buy a lot of growth, but that only lasts up to a certain point. Only a number of companies can do that because it’s a functional market that you have available. One of the things that are very interesting about the times we live in is that we live in a world where we have the biggest markets available in terms of the number of customers and companies in those. We live in a world with the biggest markets ever and the most accessible ever because everyone has a smartphone in their pocket and a credit card attached to that. It’s a lot of new dynamics that are different compared to many years ago where getting in front of customers was a very expensive endeavor. Nowadays, not so much anymore. That unlocks a whole city’s off new dynamics and behaviors, which are very interesting to observe.

B2B 6 | Lead Scoring
Lead Scoring: Go-to-market strategies have a ceiling. Eventually, they start to work less effectively than they did before.


You mentioned about AdEspresso when you started it. There was a Facebook audience and Facebook usage taking off on a daily basis. On the other side of the Facebook platform, you have the advertisers and into the edge, Facebook was investing a whole lot because, at some point in time, they need to monetize. How did you run to the idea of creating this platform for advertisers and what were the steps you took to test and get traction with the initial set of advertisers? After you land 5, 10, 15, 20, you see a blueprint laying out but learning was 5 to 10 is a key.

It’s a combination of two things. On one side, AdEspresso was born out of a need that we have as a concept. We were the first customer of the product to some degree and we are very clear. My cofounder, Massimo, had an agency back in the days when he was building products for bigger organizations on one side, on the other managing small Facebook advertising budgets on it. That’s one insight. Being the first customer always helps a lot because you have a lot of expertise, knowledge, as well as insights into what’s working, what’s not working and what the need of other people like you. The other piece of insight is tied to the realization that because Facebook back in the days was this new and upcoming ad channel that was trying to compete with Google.

They had stolen Sheryl Sandberg from Google to go and replicate the Google Ad infrastructure inside Facebook. The special insight that we had was realizing that there was a mid-market study that other companies were not necessarily paying attention to. If you looked at the Google history, you could clearly see that they started from enterprise big brand type of spenders and then bought down-market to the mid-market, and then smaller guy type of them. You can imagine that Facebook would follow a similar path. If you cared more or were particularly intrigued and interested in that mid-market space if you squinted, you could see that these people or this new wave of advertisers would be having money to spend but not much knowledge in how to do it. There was the opportunity in enabling them to tell that story through content, which is what we did and how we ended up winning the market and being a big household name when it comes to Facebook advertising.

Having that key insight was very smart of you. You say your cofounder, Massimo, who had that insight into, “As our customers, we are running into the same challenge that other advertising partners and customers would have.” The takeaway for me from all of this is where the big company like Facebook and Google are going after the bigger brands and the bigger budgets but then there’s a runway of, which is exactly what you tapped into, “No one is addressing the mid-market or even the SMBs or how do you tap into that pocket.” It’s a great learning experience for me as firsthand from all the experiences or insights that you have there. Switching gears over here. You did touch upon this, Armando, which is if you have to say the 2 to 3 paradigms into your common thread across the startups that you have gravitated towards from an investor or even startup that you founded. What are the common threads, if you will?

In terms of things that are different/have changed.

If you give an example of what you mentioned about AdEspresso.

There are a bunch of things that are significantly different. In particular, when it comes to go-to-market, the most fascinating thing that I observed over and over again is that if you think about now versus 10 to 15 years ago, it’s interesting because we tend not to think about it, but the internet is more than 25 years old, which is nothing if you think about it. We are the last generation that is going to remember a time before the internet. You think about the new generation, it’s like, “They thought it was there already. It was already a thing.” There was no ICQ or like that weird stuff. If you think about that and years ago, there was a significantly smaller number of people online.

An order of magnitude. If not, almost two. It was significantly more expensive to reach those people and was inefficient in building a business relationship that would lead to the transaction. Those are all things that are fundamentally different days compared to then. There is an order of magnitude and more people online that it’s significantly more efficient and faster to be able to establish that relationship with them and to turn that into business or relationship to get to the point where you execute the transaction. It costs almost nothing. It’s not nothing but comparably, it’s cheaper, faster and efficient to be relevant. I thought whenever there is an order of magnitude more of simplicity, there is also another magnitude more of competition.

It’s easier but also more crowded. It’s easier to reach them out, but how it stands out. It’s a different game in that sense because it’s not about being efficient as possible in reaching those customers out. It’s how do you stand out compared to everyone else who’s trying to do the same thing and reaching them out with the same level of efficiency. It comes down to that content adamant that I was mentioning before like, “What’s your story? What’s your brand? What’s your unfair advantage in terms of better perception or telling the story that’s closer to the segment or the cohort or the vertical of customers you’re trying to attract?” In that sense, going back to the other element around markets being the biggest ever, one of the things that are very interesting to me is that years ago, you will have niches of verticals of needs and problems that would be very small because many people are having those problems.

Brand has power. It talks about the story and the story is everything to people. Click To Tweet

Now, those issues are tens, if not hundreds of millions of people or companies. You see these companies that are very super niche, very specific, and deep in how they define themselves and speak to an Ideal Customer Profile, an ICP. How they define that, they are specific in that as well. Because those niches are as big as ever, they end up being companies that are $10 million, $15 million, $20 million, $25 million, $30 million, $50 million companies a year. That is the single most fascinating thing that I can think of when it comes to go-to-market. The companies that end up winning now are better at this new game of standing out and how you do that in this new playground where everyone can be efficient as everyone else is a new compelling problem to address.

You have few thoughts and few comments over there but starting off on a lighter note, you mentioned something very relevant. By the way, we are disclosing our ages over here which I have no qualms around is we are the last generation and after our generation, everyone we’re born with the internet. On that, I took my kid to one of the safest local cities over here. He went and looked at one of the vending machines. By default, he was touching the screen and expecting that screen to be a touch screen. I thought that was funny and that’s something the audience would love. A couple of points, you mentioned about companies that are vertical and niche-focused and that itself is a very large space.

I’m sure there are several but one of the names that come to my mind is Veeva. The CRM for the healthcare industry. You’ve got big elephant or their Salesforce. When you talk about CRM, it’s Salesforce, but then you got the other players who are also making it big, which is Veeva and Surado. Your point is well-taken and well-noted which is you can pick a niche or niches depending on which part of the geography you’re from and you can create a big play for yourself because that’s a big market. Another example that comes to my mind and I was at the startup earlier in my career before I started my company. I was at Greenbits. Bits are essentially doing point of sale and compliance software for the legal cannabis industry.

It does a huge and growing market. You talked about point of sale, you’ve got Square and several others, but then you focus on the cannabis industry, you’ve got all these big players. Small players but aiming to be big. One other point that caught my attention in your narrative is the emphasis that you invest a lot in the story and the brand from the very early days of your startup. Not many founders do that. That’s a flaw in my mind.

We live in a world that’s extremely DR-oriented. You can measure anything and everything. It’s a very analytical and direct response. You put $1, you want to get $1.2 out. That’s good. The fact that you can do that is mind-blowing. If you think about it, it was never the case before. That as a consequence, thus take away a little bit of attention from this idea of a brand and brands have power. Brands talk about affinity and stories are everything to people. You use brands up there like Nike, Apple and Disney, there’s nothing more powerful than that.

This is where you are having that go-to-market DNA within yourself, that’s given you an unfair advantage compared to other founders who typically come from a very technical background. They don’t think about brand and storytelling from day one. Hats off to you and your team for investing in that from day one. That’s a good segue into what you’re doing with your latest startup. Do you want to share some story and background around that as well as how you’re investing in the brand? I looked at your website, it’s amazing. I can imagine those visuals and associate them with your company. I let you share those details with our audience.

The name of the company is Breadcrumbs. It’s a simple idea. We talked about this idea of efficiency and efficiency growth. The idea of marketing being a core of every company is a growth engine. The reality is that’s necessary but that’s not enough particularly in a world where you can attract a lot of attention. At some point, the vast majority of the companies that can do a good enough job will attract some attention. One of the elements that are always forgotten or thought about too late, or not truly understood. As a consequence, you dump a lot of resources and a lot of time to get an okay result if not crappy result is this idea of the scoring and fortification or how an MQL or Marketing Qualified Lead, becomes a high performing SQL or Sales Qualified Lead.

If you think about this element of the intersection between marketing and sales as functions within organizations, it speaks about lead scoring. The way this happens from a mechanical perspective is lead scoring. Lead scoring is an unsatisfying concept. It’s a simple idea but poorly implemented. You get a lead, you score this lead, you assign a body to this lead based on a series of criteria like how big is the company, how much revenue and funding, how many customers, geography and which industry. You then pass it over to your CRM and you put in the date. Every operator knows that following up on promising lead tomorrow versus three weeks from now is fundamentally different. The time element, there is a decay of that value. There is a shelf life that’s not yet accounted for in this system.

B2B 6 | Lead Scoring
Lead Scoring: In this environment where everyone can be as efficient as everyone else in reaching the market, the companies that end up winning are the ones who are better at standing out.


What we believe is that it should be a more sophisticated way of thinking, talking, measuring and acting on these leads more programmatically at scale, more dynamically including this time element. Not only the time element, but there is also conversation around lead scoring being most of the time a BlackBox. No one ever in the history of the human species ever trusted the BlackBox. It’s your company, you want to know what is going on. You want to see what’s inside. That’s another fundamental flaw of how lead scoring has been thought off so far. What we are doing with Breadcrumbs is we want to give people more freedom and a simple easy-to-use interface to create and design their own lead scoring model in minutes instead of weeks of work. It’s not only faster but it’s also better because it does take into account that timeliness element that no one has considered. That’s the idea around it. We’re building a product. Hopefully, it’s going to be useful for other people out there.

I personally have seen having run marketing teams in different companies earlier. I’ve seen initially early on, there’s no lead scoring. There’s this constant fight between marketing and sales. The quality of leads you pass, you are just meeting a quota, but I’m not meeting my sales quota. That constant tussle is there. If you go to the next level, which is, “Now we start assigning a score to each lead, it’s more of a personal opinion and bias versus taking the data out there.”

The relationship between marketing and sales is flawed all the way through from the very early stage to the very later stage. If you think about it at the core, that type of antagonism is due to the fact that marketing measures in a very quantitative way. How many leads are you getting on a monthly basis and sales measures leads in a very qualitative way? How many of them are closing and how fast? There’s a fundamental disconnect between those two things. There is a need for something that translates one language into the other from your marketing stack to your sales stack or from your marketing teams to your sales team.

There is more general awareness and acknowledgment that’s happening. At least, I’m seeing based on the marketing and sales leaders I’m speaking with which they do realize the friction and they’re consciously looking to address that now. If I hear or speak with any of the VP marketing or even the CMOs, back in the days, it was the top KPIs or MQL are traffic coming in. Now, there’s a lot of awareness and alignment on, “That’s good to have metric but the real metric is how many leads am I giving for the sales to close this quarter or this year or the next quarter?” There’s that element which is marketing celebrating that they hit their MQL quota versus marketing is celebrating their sales hits, their number for the quarter. That shift is happening now. I’m seeing that.

Everything is crazy if you think about it. We can talk about this however you want. Now, information is still very siloed. If someone visits the pricing page of your website five times, we don’t know about that. If someone starts and is very engaged with the product, someone else from the same company signs up for a trial, and someone else visited your pricing page, you want to know about that. There’s traffic around not only timeliness but also frequency, recency and the costing of that activity in time. There are activities happening very close to each other disproportionality amplifies value. That also is not captured or represented in any way.

People talk about intent to purchase and all of these are key attributes. Unfortunately, there’s not a lot of technology out there to build and incur with that intent. The aspect that you are mentioning, I’m eager to see how it takes off. I’m cheering for you guys. This is a core problem in the go-to-market space and I’m looking forward to the success story of that.

It’s mind-blowing to me thinking about this. One of the reasons why we started Breadcrumbs in the first place is that even the most sophisticated people, the ones that do it like it should be done, spend six months and several hundreds of thousands of dollars to implement iteration one. Because it’s so time-consuming and energy-intensive, they never touch it again. Meanwhile, their social organization or their marketing organization changes. Their strategic priorities as a company and pricing structure change. The idea of having something that’s significantly more flexible and not only you can implement it in minutes instead of weeks, but you can iterate on it as quickly.

It’s extremely powerful. The most sophisticated people not only have one lead scoring model, but they have multiple ones. They have one for acquisition, attention, upselling or sale. Not only they have one for each and every one of these things, but they test multiple models in parallel to see which one performs the best based on which assumption. The more you can enable that, the more you can enable companies to be successful in accelerating their growth trajectory because if you can identify programmatically higher-value opportunities for you as a company and boost them up to the sales team, everyone’s going to benefit from that.

Based on what you’re saying here, there’s some sense of a machine learning aspect that’s going on. The machine has to do the job which people are either not capable of doing or it’s time-consuming that they ignore to do that.

The most sophisticated operators think about growth as something that can be designed through a combination of strategy and tactics. Click To Tweet

I saw a counter-intuitive thought there. If you talk with a lot of people in the industry, they will speak about ML for a long time and they will use this in their pitch as well. We think that machine learning is valuable. We also think it shouldn’t be the whole story, meaning that what machine learning can do is essentially digest a whole lot of data and find others there and surface things that will be hard to see or hard to compute otherwise. That’s by and large. What that doesn’t include in the conversation is what about the strategic direction that the company wants to go after for the next 6 to 18 months. Even if you are an enterprise company or your customers have been $50,000 ACB but either shape wants to go downmarket. Optimizing for and prioritizing $25,000 to $15,000 ACB, machine learning is not going to know that. How do you balance those two things out?

Data model and data modeling is a vast topic in itself. At some point in time, I would love to get a data scientist to talk about the impact in the go-to-market but that’s a topic for a different conversation though. I’m sure you’re spending a lot of time there but in the next 6, 12, 18 months, what do you see are the key go-to-market challenges are broadly the challenges for Breadcrumbs.io?

For us specifically, but you can generalize this to every company. Going back to the two things that I mentioned. On one side, how do you stand out in a world where everyone can reach anyone very effectively and how do you do it better. It’s a very interesting question. We can talk about tactics there.

The story, brand, colors, and visuals that you have on the website is pretty cool. It’s one part you need to scale it out and see everything.

I appreciate that. I love it. The other thing is how do you tie things back to growth? You can do a great job at all levels and then struggle anyway to generate revenue and/or to grow. One of the fundamental ideas that I’ve been thinking about for a lot and partially led to this Breadcrumbs initiative or, in general, it’s a very powerful idea is engineering growth. Meaning when the word engineering usually refers to technology and product, how you build stuff and that’s usually coding. If I think back to AdEspresso experience or the companies I’ve been involved with, what I see is the most sophisticated operators. Thinking about growth in terms of some things that you can design and the way you do that is a combination of strategy and tactic. Tactic for the short-term and strategy for the long-term.

You always have these three timeframes in front and center, short-term stuff, mid-term stuff and long-term stuff. If you think back to the most successful companies out there like Facebook, Google, Uber or Slack, you look at their growth trajectories, you notice, most of the time, inflection points. It’s breaking points where they were going in one direction and at some point, they tipped up and afterward, they’re going in another direction. What happens there? That was sometimes happen by chance. Other times, it was intentional. It was researched and experimented on for a while and implemented the right way or they had been implementing this for six months and waited for the right moment to deploy that. If there was something that was interesting to you at some point, but I think the most sophisticated operators or go-to-market growth revenue people out there, they most of the time, think about growth in this sense.

They’re the usual set of tactics, milestones and goals that you need to hit when you are in a very early-stage company. That’s a playbook that you’ve done over and over. That’s the least of the challenges for you and the team and then there’s the market aspect. You can control the market only so much. There’s not much but you are investing in the story, the brand and your milestones that you want to hit over the next 6, 12, 18 months. It’s a good initiative there. If you were to look at and share some of your investment areas if you were to hire 2 or 3 hires in the next 6 to 12 months, who would they be and why?

We’ve been covering the bases. Strengthening the engineering team, marketing, sales and support. Now, we are looking at the sales function. That would be the structure for and at this point with the company, we are about fifteen people involved. With that specific addition, we are going to have our base covered. For the next 3 to 6 months, it’s going to be a function of growth and market validation. Engineering, product and design would be a topic. You can never get enough of those. One thing in operations, we didn’t strengthen too much operations just yet. It’s going to be a topic very soon.

If you are to extrapolate, you’re going to invest in the product side, engineering side, sales of course, and the revenue. In Breadcrumbs.io, who is your target market for the next 6 to 12 months? Is it the small, medium size, similar to what you did with AdEspresso? Is it the enterprises or a mix and why?

B2B 6 | Lead Scoring
Lead Scoring: There is a need of something that translates one language into the other from your marketing stack to your sales stack.


It’s mid-markets. One of the other thing behind Breadcrumbs is people or companies think about lead scoring too late in the game, they should start earlier. We want to start early with them and grow with them. We want to help them grow and we want something that’s easy to set up and implement at first. It grows in sophistication as the complexity and maturity of the company grow as well. It was more of that growth, but we do want to start simple, easy early. In that sense, the companies we are optimizing or focusing on for now are generating $1 million to $5 million or $2 million to $10 million types of annual revenue. They have a marketing engine that works that’s generating a few hundred leads per month or more. They have a system motion, so they have an initial sales spot off and a couple of people that they hire. It’s the initial adversarial relationship, marketing and sales and things that are not picking up yet.

At least, from a hypothesis point of view and even from a validation point of view, that’s a good sweet spot to start off. That’s where the most pain is felt initially. Coming back to my Greenbits days where I was the head of marketing there, I see that we were in the single-digit like the $4 million or $5 million range, and that’s where the whole marketing and sales friction as the CEO and the CROs say, “Get me the leads.”

That’s the sweet spot when this topic becomes when we get paid.

We are heading towards the closing. I know you need to get back to other more important things for Breadcrumbs.io. One final question for you is if you were to do a shout out to 2 to 3 professionals or peers in the industry who are doing go-to-market very well, who would you look up to for inspiration, advice or brainstorming?

The company that I very much admire, which is HubSpot. They’re doing an extremely good job at go-to-market. They have been for a long time now.

Can you speak names there?

No, but they are doing a great job. For younger companies, no specific name comes to mind. The golden standard for me is absolute when it comes to go-to-market both because they have a lot of the elements that do contribute to a healthy growth trajectory. You can see that in their revenue. They have an inbound first. Atlassian is another one. They have an inbound first type of go-to-market like a bottom-up. You should list up very cheap and they end up being very expensive. They have a cross-sell, upsell type of mechanics that they built in the product. They not only have self-service of great paths but also commercial enterprise ones. It’s the most sophisticated go-to-market that I can think of right now.

I can see where your inspiration for your go-to-market is coming from. It’s the bottom-up approach. It’s clearly there. It’s a wonderful conversation, Armando. Thank you for your time and good luck to the Breadcrumbs team and to you as well. I’m looking forward and I’ll be sharing from the side.

Thank you so much and best of luck to you too.



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About Armando Biondi

B2B 6 | Lead ScoringAs part of Hootsuite’s Senior Leadership, he oversees all things Ads from a GTM/strategy perspective. He also oversees all things Inbound on a series of properties generating more than 2M unique visits monthly, as well as other high-potential special projects.

-Co-founder @BreadcrumbsIO (previously Co-founder & COO @AdEspresso, acquired by @Hootsuite). Angel investor in 150+ startups. Board Member @MailUpGroup.

He also served as a Mentor/Advisor for more than 15 startups and currently serves as an Independent Board Member. He likes to pay forward and have fun doing some angel investing (75+ startups so far). He love to learn new things, he accepts to suck until he becomes good, and doesn’t stop until I’m awesome.


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