B2B 12 | Strategy Execution

B2B 12 | Entrepreneurial Mindset


Nothing can come out of an excellent business strategy if the people behind it lack consistency and focus. Therefore, everything on the marketing side boils down to proper strategy execution, which involves communication and collaboration. Vijay Damojipurapu sits down with Jeremy Epstein to talk about how every CEO must learn the ins and outs of marketing or risk becoming ineffective business leaders. They discuss how well-targeted implementation of strategies can successfully transform marketing from a cost center to a revenue driver. Jeremy also dives deep into his work in the world of crypto and OKR as the CMO of Gtmhub, helping business leaders fully embrace the full potential of their plans and work on it before it’s too late.

Listen to the podcast here


Starting A Consistent Business Strategy Execution With Jeremy Epstein

I have with me Jeremy Epstein, who is the CMO of Gtmhub. Jeremy, welcome to the show. I’m super excited to have you on the show because of your varied and colorful background. I say that with good intent.

There’s no person involved?

No. You are big on crypto. I’m eager to pick your brains on how you end up there and what you’re doing there. That’s interesting.

We could do that all day also. 

Besides that, you’ve grown a marketing career. I’m eager to peek or tap into your head and wisdom and get all those nuggets out for our readers. We can go on and on. We see Neeraj Agrawal who called you as one of the top go-to-market experts and who gets growth marketing. Kudos to that. I want to get the story as well from you.

Thank you. It’s an honor to be here.

There are only two responsibilities that an organization has: innovation and marketing. Everything else is a cost center. Click To Tweet

Welcome, Jeremy. I start my show with this question. I pose this to everyone and I’d like to get your take on this. How do you define a good market?

It’s the combination of strategies and a series of activities that you’re going to do in order to help your intended customers and prospects understand your value proposition.

As simple as that.

At the end of the day, if I want to get even simpler, it’s, “How am I going to tell our story?”

There are a lot of pieces below that. Is that a top-level?

You did ask me how I define it so that’s how I define it.

B2B 12 | Strategy Execution
Strategy Execution: A good market is the combination of strategies and a series of activities that can help your intended customers understand your value proposition.


That’s a good start, Jeremy. That is exactly what we want. If you need to unravel it and make it more consumable or actionable for our readers, what is your thought process around that? 

Especially when you get to the CMO and VP of marketing level, the fun part is coming up with the strategy. That’s what everyone is paying you, the theoretical big bucks. You get to do all the whiteboarding and come up with the game plan. If you’re a reasonably good marketer and you made it to that level, you probably have a decent strategy. Good for you. Where things start to fall apart, though, is in the execution of the strategy. How effectively are you building a team? Most importantly, how effectively are you communicating what your strategy is? If you talk to people in the marketing function, the number one thing that they’ll tell you that they don’t like about marketing leaders is an inability to effectively communicate. It’s ironic because marketing is all about communication. Here we are, we come up with these grand strategies and then we start to fumble the actual explanation of, “How is this going to work? What are your responsibilities?”

I get super passionate about this sometimes. When I think about the go-to-market, it’s my job as a leader and any marketing leader to say, “Here’s our game plan. Here’s the audience we’re going to go after. Here’s the series of activities I want to do.” More importantly in saying, “Vijay, you’re responsible for this. If you do this, I’m going to carry you off the field and dump Gatorade on you and my hero. If you don’t do this, I’m going to take you out back and shoot you.” That’s how it works. It’s very clear roles and responsibilities. That’s how I think about the go-to-market. It’s the measurement of, “I made some assumptions about what we were going to do. Was I right? What were the experiments that I ran along the way? What was the hypothesis that I have? What do I now know that I didn’t know then?” I’m continually iterating about that, but it’s alignment. Go-to-market is about aligning your team behind the strategy and giving them clarity across teams and the various functions and roles so that everybody can understand, “Here as an organization, this is what we’re going to do to drive our marketing objectives for the quarter of the year, the decade or whatever you’re doing.”

You articulated that very well as always, which is a series of activities. In short, it starts with that. Where a lot of marketing teams fumble is more than the execution pieces and it can be across communication within the marketing team where the leader is not clear or the team members are not clear. Even if that individual, let’s say it’s the growth, demand gen or content person is clear, but there are a lot of gaps and what I call as the multiplier effect, which is, “If we are marching towards a launch, what is growth and demand gen doing? What is content doing? What is field marketing doing? What is the brand marketing doing?” All of those pieces have to line up to that one consequential event.

You’re 100% right and I’ll throw, “What is sales doing? What is the product doing? What is the support team doing?” I like to say we’re all in marketing. It’s just that some of us know it. My all-time favorite marketing teacher is Peter Drucker. He said, “There are only two responsibilities that an organization has, innovation and marketing. Everything else is a cost center.” Our job is to make it clear, especially if you’re working with global teams. I have people in six different countries that are on my team. Communication is even more important because I have to be mindful of not using, say, American football analogies or using a movie analogy because it’s not obvious to a lot of people, especially people for whom English is their second language. I need to be mindful. As leaders in a global world, we all are. That’s where we have to be thoughtful in how we drive the execution. It’s great. Everyone’s strategy is fantastic but at a certain point, it’s like the Mike Tyson thing, “Everyone has a plan until you get punched in the face.” As soon as you launched the campaign, you’ve gotten punched in the face.

You also mentioned something that Peter Drucker called out. You’ve got product or innovation. You’ve got marketing and everything else is a cost center. Peter Drucker mentioned it in the ’60s or ’70s. I don’t recall the exact timeline. It was early. Somehow, somewhere along the line, things got muddled. The reason why I say that is, if you look at marketing at most organizations now, they are seen as a cost center. The number one reason is because marketing is not carrying the revenue burden that the sales team is carrying. I’ve looked at your track record and background. You’ve got a very accomplished track record. Somewhere along those lines, your thinking must have shifted. Can you share your journey when you started your go-to-market journey, but emphasizing how the thought process has evolved from, “Marketing is not just a cost center, but I should be a revenue driver?”

At a certain point, every business has a plan until they get punched in the face. Click To Tweet

I’ve been very fortunate along the way to work for forward-thinking leaders. Too many marketers, especially when they’re starting out their career, they’re not reporting to other marketers. They’re reporting to CEOs, founders or COOs who don’t necessarily understand. They think marketing is a trade show booth, T-shirt and bumper sticker. That’s part of it, but that’s not what it’s all about. Marketing comes down to awareness, perception and leads. Everyone thinks about the leads, but they don’t think about awareness and perception.

In my journey, I didn’t study marketing. I studied history in college. I like to say that history and marketing are the same disciplines. It’s just storytelling, combining facts and stories. I started my career during the dot-com era first in Tokyo for a marketing agency there where I read my first marketing book, which was The One to One Future by Don Peppers and Martha Rogers. That set me on the path and formed my thinking. I moved into sales for a couple of years. In New York, I had my own startup company, which was TaskRabbit but a decade too early. We missed that one. I worked at Microsoft in some marketing roles and a lot of channel development roles. Microsoft is where I learned about the operationalization and scale of marketing. That’s where you start to understand, “It’s great that you do all this cool stuff, but if it doesn’t have an impact in some meaningful, measurable way, then you’re wasting everybody’s time and money.”

The big thing for me happened when I started to play around with social media. I’ve been an early adopter going all the way back to my first Mac in 1984. I was blogging since 2000. I was number 186,000 on LinkedIn or some point in that, and Twitter in 2007. I started to understand that the arrival of social media would change the nature of marketing from this broadcast one-to-many mass discipline to everything that became a conversation. It became about relationships and understanding that there’s a person on the other side of the conversation. You want to monetize it, but you have to think about the value. What is the value of this relationship to them? The marketer’s job is to think from the other perspective.

I had the good fortune to be the Head of Marketing at Sprinklr for four years, from our Series A financing round when we had about 30 people at a $20 million valuation until we were hit unicorn with a $1.8 billion valuation and 1,400 people. That was a crazy ride. Again, I was blessed with a phenomenal CEO who said, “Yes, I want you to drive the revenue.” I understand that revenue is going to come when you do things that make other people feel valued in a relationship, conversation and community. That’s what helped me see the whole thing. I started to understand, “You have to think about your activities in terms of outcomes, but the way you achieve those outcomes is by treating people right.” Treating them well, doing the right thing and having confidence that you may not be able to attribute every activity to every single thing. That doesn’t matter. If your strategy says, “I’m going to do the right thing, treat people well and give them reasons to talk about us in this social media empowered world,” the value is going to show up. That’s been my philosophy. It doesn’t work for everybody, but it works for me.

You’ve given a good formula out there. You are the living proof of that mindset. The thinking shift has fairly driven your career growth. Kudos to that. There are quite a few points that caught my mind when you were talking about your journey. One is having the good fortune to work with a CEO who gets marketing. Unfortunately, not many CEOs get marketing. You did call a few points under that, which is, marketing is not just about swag or stickers. It’s a lot more than that. You also emphasized the point of, “The ability to create a community and drive value, you’re doing it one-to-many, but keeping that one person in mind.” That’s when the actual transaction happens. These are great points. Especially for those who are looking to grow in their career, my advice which you validated yet again from another accomplished marketer, is to look for that leader or the CEO who gets marketing.

If you’re in a situation where you’re with a leader who may not get marketing, you have a responsibility to yourself. If you care about marketing, even though it’s scary as all can be, that’s where you go. You have to have that come-to-Jesus moment as it were and say to the CEO, “I can do all these things, but that’s not marketing in its truest sense.” The way that I explain it to non-marketers, I said, “Marketing is like a wedding cake.” They were like, “What do you mean?” I said, “Look at a wedding cake. Everyone pays attention, ‘Look at the decorations and the flowers. It’s beautiful,’ but that’s 6% of the cake and 94% of the cake is a boring batter. If you don’t know how to make the batter, put it in the oven and have a cake that’s not going to collapse when you stack it on one level on top, it doesn’t matter how much icing you put on afterwards. It’s going to look like garbage.” Everyone else is like, “Look at all the icing.” I was like, “Forget the icing. You want people who know how to bake cakes. If you know how to bake cakes, you can learn how to put on the icing. If all you know how to do is the icing and you can’t bake a cake, you’re just going to have a big pile of junk and your marketing is not going to work. Which do you want at your wedding, Mr. or Ms. CEO?”

Strategy Execution: Go-to-market is about aligning your team behind the strategy and giving them clarity across teams and the various functions and roles.


As you are describing that wedding cake, this visual came to my mind. If you look at the stacked wedding cake and flip it, it’s your funnel. There are a lot of activities in those behind-the-scenes, that ugly batter that you were talking about, but once it’s done well, that’s when you get that sweet-looking funnel.

That’s the best build on the marketing wedding cake analogy I’ve ever had. It’s nicely done. No one’s ever come up with that before.

Continuing our fun-filled but insightful discussion here, how would your parents or kids, depending on who you want to choose, describe what you do on a daily basis?

My kids are baffled. They don’t even know what I do on a daily basis. If I had to be all kidding aside, my wife might say, “My husband tells stories about the near future.” What are the things going to look like? I try to say, “There are all these trends going on now. Remote work.” Now, it’s obvious to everybody. These things were happening before COVID hit us, but now they’ve been accelerated. It’s not so much, “What are we doing now?” It’s, “What are some of the likely outcomes as a result of the arrival of social media, COVID, mobile phone, blockchain technology? Pick your thing and then try to tell people. It’s that overused cliché, but it works well, which is Wayne Gretzky’s, “Skating to where the puck is going.” I try to tell stories like, “Here’s what it might look like in the near future.” All I’m suggesting is, “Here’s what we can do now so that it’s less painful to adjust than it would be otherwise. It’s a lot easier to make the one-degree shift now or two years from now than the 90-degree shift in two years.” I try to tell stories and paint pictures of the near future for people. They might say that or say, “My dad is crazy. I have no idea what he’s doing every day, but he seems to like it.”

How do you do your job? How do you tell stories? What do you do at Gtmhub? Explain that to our audience.

I’d be a pretty bad marketer if I didn’t at least explain what Gtmhub is. We are an enterprise-grade system that’s based on the objectives and key results methodology that helps companies of any size orchestrate consistent strategy execution across their teams, divisions, business units and geographies. We talked about strategy execution before. We have come up with the strategy, but OKR has given you that approach. It’s proven. This is a methodology. We talked about Peter Drucker. It has its origins in Peter Drucker’s work, goes to Andy Grove in Intel in the ’70s and popularized by Google in the early 2000s. With OKRs, I am 100% convinced. Do I have skin in this game? Yes, I do.

If you're in a situation where you're with a leader who may not get marketing, you have a responsibility to yourself. Click To Tweet

Once you read this Seminole book on OKRs, which is Measure What Matters by John Doerr, I tell people, “If by page fifteen you’re not convinced this is the methodology that every company is going to use by the end of this decade, I’ll personally refund the cost of the book.” I’m not willing to do that for every single reader, but I probably am because it’s that convincing. What I try to do are two things. For people who have already decided that OKR is there for them, what I like to call they have OK Religion, I help them understand why we are in fact the most flexible and most enterprise-grade system from among all the competitive sets. There are some very worthy competitors out there. I personally think that they’re overly rigid and designed for a different era. Ours is designed for a much more multilateral, multi-axis world. That’s number one.

The second is for people who are maybe not as familiar with OKRs. We don’t talk about it. What we say is, “You have a challenge around horizontal alignment. Everybody knows that. You have a challenge where you might have a lofty vision or mission statement, but day to day there’s an inconsistency between your execution and what your stated objectives and goals are. We have a way that if you commit to it, you’ll be able to achieve your objectives consistently, which is to be inspired. It’s based on this methodology known as OKRs, which we can teach you. It’s easy to learn. You just have to commit to it.” I’ve put together the strategy. I recruited the team, which I’ve been fortunate. I’ve been able to get some phenomenal world-class players. I try to support them to be the best versions of themselves that they can be and then get out of their way.

What every top CMO does is show the path and let the team do the work.

The hardest part of my job is coming up with my own OKRs. Once I set my OKRs, I can communicate to the team and then we collaborate on everyone else’s. If I do a decent job and set the strategy, objectives and key results well, then the team flows in. It’s a beautiful thing to watch. It was almost like there were days where I thought, “I don’t have enough to do because my team is executing. I’ll go for a walk.” I’m so fortunate to be in this environment. That’s what I try and do. We have a lot of work to do. That’s some called kidding aside.

I did a quick bit of research on Gtmhub. Something that you guys do from a go-to-market for Gtmhub is you have a podcast. That’s one piece. You also have the social media pieces going. Of course, you have the field marketing and enabling the sales because you serve a lot of enterprise-grade companies, which is a complex enterprise buying cycle. Talk to me about the podcast. The reason why I asked this is when I speak with the VPs of Marketing in either my client’s or someone who’s interested in knowing what I do and how I can help them, a constant topic that comes up is content. Content is currency, but a lot of people do not know how to do content well.

Our philosophy when it comes to pretty much everything but certainly content is that no one cares what we say. They only care what other people say about us. What we try to do is create platforms to give other people a voice. Our podcast, which Jenny, our VP of Marketing, hosts, is called Dreams with Deadlines, which I think is one of the greatest names of all times. It’s been growing like gangbusters. It’s the number one podcast in the OKR space. She brings on leading practitioners, leading partners and thought leaders who are pushing the envelope in terms of what OKR is and gives them an opportunity to educate. We just want to educate. That’s all we’re doing.

B2B 12 | Strategy Execution
The One to One Future: Building Relationships One Customer at a Time

We have a series on our blog called Voices of OKR where we give other people and practitioners, “Here’s how we do it. Here are the mistakes we learned.” We have something we call the OKR Champions Roundtable where we invite our OKR champions. We’re blessed with some of the largest companies in the world like Adobe, CNN and Red Hat. Many phenomenal names like Société Générale and many others. We have over 800 customers and 100,000 users in 75 countries. We bring them together and give them an opportunity to talk with each other about the challenges that they’re facing. For me, content comes down to allowing your customers, prospects and community. I’ve even given a platform to people who use competitive products. I don’t care. I’m here to educate. I’m here to help because that builds trust. If you build trust and you say, “I’m just here to help.” Do you know what my real goal is? It’s to get every one of my clients promoted. That’s what I want. If I get you promoted, we’re going to be in good shape.

How can I help you be smarter, better, more informed, make an easier sale to your boss? That’s what the content is. We put out a buyer’s guide. We call it the 51-step Guide to Avoiding OKR Career Suicide. It’s all the things you should think about. We talked about, “Here’s what you need if you’re buying an enterprise OKR system. Here’s why we think you need it. If you don’t agree with us, throw it out the window.” At the beginning of the introduction, the first page is, “We’re an OKR enterprise software company. Do we want you to buy our software? You bet we do.” We know that. We don’t want to run into that issue so we’re going to tell you, “Here’s how we’re thinking about this. If you don’t like it, burn this thing. We don’t care. We’re just here to help because we’ve been doing this for several years with all these companies.” I guess the caffeine is kicking in. I’m super jazzed up. It’s you. You’re asking me great questions, Vijay.

It’s all about the serving mindset. That’s what it comes down to which is serving mindset and helping. You nailed it, Jeremy. I was going to say that it was you. “The venn is essentially helping you, Mr. Buyer, get that promotion.” That’s it.

It couldn’t be easier than that.

Shifting gears a bit, talk to us about your big goals for 2021.

From an internal perspective, I’m trying to operationalize our marketing. We raised our Series B. We closed it on December 31st. We raised $30 million, which was the largest Series B in the history of the space, which was great.

No one cares what you say as a business. Customers only care what other people say about you. Click To Tweet


I didn’t do much, but we’ll take some of the credit. Now, I’m focused on building out the marketing team and building out our operational capabilities so we can have more process and rhythm. From a marketing overall perspective, I think our awareness in the space is not where I want it to be. We’re perceived as one of the top 3 or 4 players in this space. I’d like us to be across the board and perceived as the number one player. I have a little bit of work to do there. I don’t like to call it a funnel so much. I call it the journey. We get a lot of people who are still very early on in the education process. We do have a probably lower than I personally would like conversion rate from MQL to SQL to opportunity.

It’s respectable. I would like to do a better job of finding more middle and high-intent buyers and then also figuring out for the early or low-intent buyers. What can I do to educate them programmatically at scale without spending the time on the sales? If we can accomplish those things, that will put us in a good position. The product team needs to do what they do because we’re a product company. The sales team needs to do what they do. There’s only so much I can do. From a marketing perspective, I like where our story and messaging are. The visuals are strong. It’s getting better at telling the story and some of the mechanics. It’s to operationalize this and prepare us for that next level of growth as we start looking towards a Series C down the road.

It sounds like you have primarily or heavily a top-down go-to-market, which you tackled the buyers and influencers. What is your thought process around a bottoms-up? It may not be fruitful in this scenario because OKRs itself have to come from top-down and trickle down. Have you seen that maybe it pulls from the bottom-up phase as well?

I wouldn’t call it bottom-up. I call it middle-up. I’m giving away the strategy here, but it doesn’t matter because it all comes down to execution. I can leave my strategy on the front step of my house and someone can come to take it. It won’t matter because they don’t have the Gtmhub OKR platform. Unless they buy it, in which case they would, but they’d still have to do it. The senior executives are horizontally-minded executives, people who are looking across and realize there’s a problem with horizontal alignment. That’s one thing that we look at from an executive perspective. The second thing we do are the OKR champions, the people who are tasked with implementing. It’s helping them go out, be better prepared and more informed. Most importantly, above all, it’s to feel they can trust us. That’s all it comes down to.

You’re going to pick the software company with the people and brand that you trust. That’s what a brand is. A brand is about trust. It’s about establishing trust at those various levels. We need to build relationships with both of those. The economic buyer is going to sign off, but the implementer alone has to deal with the decision. The fact that we are the most flexible platform and we do have the largest number of customers and the most amount of experience, we believe we’ll help them. Fortunately, we have many customers who agree with us. Every now and then, we screw it up. For the most part, we won’t. We’re not perfect. No one would believe me if I said we were. I might as well get that out there. I’m just here for my competition to read this, they go, “This is what this guy is doing.” Bring it. May the best OKR platform win.

B2B 12 | Strategy Execution
Strategy Execution: Many think marketing is a trade show booth, T-shirt, and bumper sticker. In reality, it all comes down to awareness, perception, and leads.


Talking about problems and all good market machinery, it doesn’t matter what size or stage of the company you’re in. You’ll always have problems and challenges that you need to deal with. In 2021, you did mention a couple, which is more around from the awareness and even to the MQL down to the conversions. Those are the pieces that you want to tackle. When you encounter such problem areas in your go-to-market execution, do you typically bring in outside experts? When I say experts, I don’t mean agencies. Of course, you have your SEO agencies or demand gen agencies. Besides that, do you typically tap into experts, and for which areas do you do that?

It’s probably too early for me to answer that. Before we got our Series B, I didn’t have a lot of money. We do. We have a relationship with a highly regarded analyst firm to help us with some of our go-to-market thinking, especially positioning around some of the executive C-Suite that we think is relevant or irrelevant. Now that we’re maturing as an organization, we are doing that both in terms of consultants as well as getting the right tools. We’re not afraid to spend on those types of things because there are plenty of things we don’t do well. You might as well find someone who’s good at it and let them do it so you can focus. That’s what OKRs are about. It’s focusing on the thing that you do well and letting everything else go to someone else who does that better. That’s certainly part of our game plan going forward.

Do you mind sharing a bit about your MarTech stack and how it looks like? That’s a mess. I’ve spoken to CMOs and VPs of marketing. People talk a lot and praise the MarTech stack, but they also have the burden of, “That’s way too many tools. I’ve been burdened with the predecessor who built this, but we don’t have any need for it right now.” What does your MarTech stack look like?

I fit into that category. I love it and hate it at the same time because there are a lot of tools out there. My predecessor did a great job, so I’m not in that particular boat. We’re based on HubSpot and then everything flows. From there, our sales team uses Salesforce. We have a nice integration there. It’s a bunch of tools that go on and connect around there. If I said everything moved perfectly, I would also be lying. There are definitely some hiccups, but there are always things that you could be doing better. There are a lot of tools, keeping track of the data and keeping the data clean. These are not new problems. It’s the same problem, but with more tools, APIs and bills coming in.

How do you track or measure signal or intent? That’s a big challenge across the board.

I don’t think we’re particularly good at it. I should have added that in. That goes to our MQL, SQL and the conversation before. It’s doing a better job in terms of differentiating buyers or visitors in terms of intent and based on activity either on-site or off-site. It’s very immature. That’s one of our focus areas. One of my team member’s OKR for Q2 in fact is around that. We’ve already written that down. She’s already off and running. She’s a little bit ahead of the game. We need to do a much better job. What we’ve done a good job on is, I wouldn’t say we solved the problem, but we have a good top-of-funnel in terms of getting those MQLs. It’s that middle of the funnel, middle of the journey that we need to improve on. How we instrument that is, like I said, a big part of our focus. That’s why writing OKR is so important. I say, “Here’s the OKR. We come up with it,” and then people are clear on what they need to do. It comes back to our clarity conversation from before.

If you deliver outcomes, no one cares how much time you spend. It's about the outcome. Click To Tweet

That’s a problem that I see when I speak with my clients or even others in the space. There’s a lot of noise out there. Buyers are inundated because of the slew of virtual events and phone calls. Phone calls have reduced a bit because a lot of people are working at home now so you don’t do the switchboard problem. At the same time, the emails, SMS marketing, all of these are inundating the buyers. One of the CMOs I was speaking with, he was saying, “One of the challenges is how to measure signal and intent correctly and help distill the signal from the noise. Not for my team, but for the buyer.” 

I’m very sympathetic. I do struggle sometimes because when I don’t have my CMO hat on, I’m like everybody else, like unsubscribe, take me off the list, blocking and what have you. I’m thinking, “Why is it that when I put on my CMO hat, I think it’s okay?” I’ve been working hard with the team to say, “If you’re not going to read this, if you’re not proud of this and don’t think this adds value, don’t you dare send it. I would rather you miss a deadline than send something that’s crap because it’s going to hurt the brand.” Nobody thinks about, “What about all the people who unsubscribed as a result of this bad mailing or the people who now think one notch lower of you in terms of perception?” Ideally, you hit the deadline and you have quality. If it comes down to it, I’d rather you go another day. I can’t sacrifice the brand just because I said, “We’re launching on March 18.”

We can go on and on. We talked about OKR, marketing conversion problem and signal and intent. Before I ask the questions, there is also another unique aspect to your colorful background, which is crypto. Tell us about what triggered you or what got you into crypto? What are you doing now about that?

I’ve been deep in the world of crypto for the last five years. I joined Gtmhub back in June. For the 4.5 years before that, I was working in the space as an advisor to some of the leading startups. I was the Co-Chief Investment Officer of a crypto hedge fund. I’ve written three books on it. I’ve had the opportunity to brief three-star generals at the Pentagon about crypto, given keynotes and what have you. I fundamentally believe that it’s a foundational transformative technology. It’s a key passion. I think cryptoeconomics is one of the most incredible things that’s ever been invented. I am fortunate that Gtmhub and my team are extremely supportive. It’s my 20% time.

I spend 20% of my week on my crypto-related activities, including managing the fund for my investors. We returned 92% in 2020 so that was good. Advising some of the startups in that space and continuing the blog. I probably had 657 blog posts and another 100 articles on it and evangelizing, studying and understanding it. To me, this feels like the arrival of the internet, but for value. It’s significantly bigger. The part I’m excited about is when I get the opportunity to merge these two worlds. When I can start bringing in cryptoeconomics, cryptocurrencies, non-fungible tokens, decentralized autonomous organizations and all of these concepts that I’ve been playing around with, bring them into Gtmhub to further differentiate our marketing and add value for our customers, that’s going to be epic.

The good news is I have a CEO who is fully supportive and a team that’s excited about it. Until they take me out back and shoot me, I’m going to continue to pursue these two paths. It seems weird like, “How do you have a CMO who does both of these?” Our belief is that, especially when you’re in marketing, you have to get out of the business. You have to be able to look at it from a different perspective. By forcing myself to go to a totally orthogonal industry, I’m able to let my brain rest in a working capacity and then look at the market for OKRs. In fact, I’ve sold Gtmhub to 6 or 7 different crypto projects because they need OKR. Everybody is going to use them so I was like, “You might as well use the one that I work for. Here you go.” It’s a nice opportunity to work on the cutting-edge of two big transformations. Blockchain and crypto are a huge transformation and OKRs, which are going to be the foundational methodology for business and digital transformation this decade. To work in both of these, it’s like nirvana.

B2B 12 | Strategy Execution
Strategy Execution: The arrival of social media changed the nature of marketing from a broadcast one-to-many mass discipline to everything becoming a conversation.


You hit on a very important point. Especially for marketers and even marketing leaders, it’s important to detach yourself from the day-to-day. It goes back to what Google has been doing from day one, which is 20% of the time just dedicated to non-work stuff. It keeps you fresh and creative. It keeps your energy going and you bring them back into work.

In fact, we talked about Drucker right over there. I have his book, The Effective Executive. He talks about being aware of where your time is spent, the danger that executives have from being too caught up in their own business and the need to take that step back and look at the market from the perspective of the market. That’s your job as a marketer. I wouldn’t have taken the role if I couldn’t do it, but I’m very blessed to have that kind of support. As an organization, what we represent is the kind of organization that everybody is going to work in, which is if you deliver outcomes, no one cares how much time you spend. It’s about the outcome. It’s not about five days a week. You don’t work on an assembly line in the knowledge economy. Your job is to deliver an outcome. Not output but outcome. If you deliver the outcome, we’re happy. If you don’t deliver the outcome, we’re not happy. It’s very simple.

Especially in this remote and hybrid work environment that the industry is shifting into, it’s very critical. It’s not like the managers and leaders have complete insight into our visibility to what people are doing. Again, it goes back to marketing 101 which is stressed. If you were to give a shout-out to 2 or 3 folks out there in the industry who are executing well on the GTM front, someone who’s inspiring you, giving you new ideas and you look up to, who would they be?

I think the team at Drift does a nice job. They’re sharp. There’s a crypto project called the Helium Network. They do a nice job also with their marketing and storytelling. As far as the third one who does a great job with marketing, I don’t know. I’d have to think about that. Can I get 2 out of 3? It will come to me and I’ll be like, “Why didn’t I say something?” I don’t want to say clichés like Apple or Netflix. That’s lame and capped out. I’ve got to come up with something stronger. It will come to me.

A couple of others, Gong does a good job, Gong.io. Even Clari, they are into revenue intelligence and also doing their own marketing. There are a few others. Drift, I completely agree.

Drift is tight. I’m envious of Drift.

That is the beauty. If your marketing is right, you add so much of the premium halo effect around your product. If you take that out, the product is nothing wow.

It’s Intercom. With all due respect to Intercom, I love Intercom. We use Intercom. I’m just saying, it’s Intercom. I’m going to get in trouble for this one. I hope no one reads this episode. It’s going to kill my career, but I wanted to read for you. For me, I want no one to read because my career is over now. It was nice knowing you, Vijay.

One final question for you, Jeremy. If you were to go back to day one of your GTM career, what advice would you give to your younger self?

That’s an easy one. It’s a marathon, not a sprint. I ran so hard when I was young. I realized, especially with great marketing, it’s like coming back to our cake analogy. You can’t rush the cake. 

It goes back to our Buddhist monk mindset.

I’m a wannabe Buddhist monk. That’s my problem is I want. I’m already failing at my Buddhism there. I’ve got a long way to go on the path of enlightenment, it sounds like.

Jeremy, it’s been a pleasure having you on the show. Good luck to you and the team at Gtmhub and of course, your crypto initiatives as well. We’ll cheer you from the sidelines.

Thank you for the opportunity to join your excellent show. Much success to you this year.


Important Links


About Jeremy Epstein

B2B 12 | Entrepreneurial Mindset

Chief Marketing Officer, Gtmhub

Epstein spent 6 years at Microsoft and brings a global perspective with stints in Frankfurt and Tokyo. Jeremy served as the first marketing leader at Sprinklr, navigating efforts from Series A through $1.8 billion “Unicorn” status, as the company grew from 30 people to nearly 1400 over the course of 4 years.

Known for his orthogonal approach to marketing, Epstein has written 5 books on marketing, over 200 articles, more than 1000 blog posts and is a sought-after keynote speaker, with presentations in more than 20 countries.

In addition to his significant marketing experience in both enterprises and start-ups, Epstein is a well-regarded and passionate technologist who is a leading authority on blockchain and cryptoeconomics, having briefed 3-star generals at the Pentagon and worked with some of the most cutting-edge teams in the world such as Dapper Labs and Zcash.


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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.


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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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