B2B 56 | Leading Others To Success

 B2B 56 | Leading Others To Success


Gong is a revenue intelligence platform enabling revenue teams to realize their full potential by unveiling customer reality. Today, Gong’s Chief Evangelist, Udi Ledergor, shares his secret to leading others to success. As a B2B marketing executive, Udi has showcased his expertise in leading the Super Bowl ad success. He delves into product marketing, and the product marketing’s role is to tell the company story. Join Udi in this insightful episode and see how he and Gong will help pave the path for your success.

Listen to the podcast here


Leading Others To Success: Building And Scaling Your Marketing Operations With Udi Ledergor

I have the pleasure of hosting Udi Ledergor, who is the Chief Evangelist at Gong. I’m sure that if you are in the B2B go-to-market and marketing world, you have come across and heard of Udi. Without any elaborate introductions, let’s get right in. Welcome to the show, Udi.

Thanks, Vijay. I’m excited to be here.

This is how I always open the show with a guest, and everyone likes to get right to the topic, which is, how do you view and define go-to-market?

Go-to-market is the process by which a company identifies its target audience. They understand the value that they’re bringing that target audience and how to deliver that value to the target audience. In other words, who are we selling to? What are we selling them? How are we going to sell this?

I like the way and how we emphasize that it all starts with the audience. You didn’t talk about any of the internals or the intricacies that have to happen on the company side, which is the product, marketing, sales, and customer success. You left it out, although it’s understood you are referring to those functions.

Form follows function. If you start with who’s going to report to whom and what we are doing internally, we might miss the bigger questions of who are we selling to, what we are selling them, and how they want to buy from us. If we figure that out, we can build the right org structure, hire the right people, and build the right product to deliver that value.

It all starts with the persona, the people, the segments, and the problems. It all starts and ends there. Everything else is helping the persona to address their problems.

That’s where the elusive product-market fit happens. Many companies fail to find product market fit there. There are multiple reasons that this can happen. One of them is that they were obsessed with building a solution. They’re searching for a problem that that solution solves. Sometimes, they’ll find it, but often they won’t. The other way around, where companies obsess about a problem and look for the best way to solve that problem is usually a more direct line into product market fit and a product you can sell.

I would love to get into that specific topic. Before this call, I was with another founder who built a successful company. They’re still in the early days for several years. They grew from 0 to 400 customers. They raised $18 million in funding. It comes back to what you mentioned, which is the focus on the problems and the people and continuous focus on that. Let’s go to the big picture. Let’s go broad enough. How about you share your career story and journey with our readers and what got you to what you’re doing now?

The first relevant memory would be, as a teenager, I was doing a summer internship in my father’s office, who was working at a big tech/IT company in Israel where I grew up. I saw a bunch of people slouching over their computers, typing away. I thought, “What a boring job. I’m never going to go into tech.” Those are famous last words.

I always loved the performing arts. I dabbled in magic, music, lighting, sound, and everything you can imagine in between. Marketing is the perfect grownup job for someone like me who loves putting on a show, creating an experience, and experiencing that bridge between all the sometimes complicated, messy stuff that goes on in the back to create this clean, simple-looking experience on the outside.

Magicians and musicians do that. When the best of them do it, it sounds and looks effortless. That’s what great marketing looks like. It is when you create a beautiful, simplified experience for your audience where you can simplify complex technology into a simple use case of “Why should I care about this?” You make it seem easy and obvious that, “How did not someone think of this earlier?” That’s how I got into tech or what pulled me in.

Great marketing is creating a beautiful, simplified experience for your audience where you can simplify complex technology. Click To Tweet

In practice, I served in the Israeli military for several years, as most Israelis do, at least back in my day. Towards the end of my service, I was contacted by a company that had won an RFP with the Israeli military to build a simulator for a rocket system that I was an expert on at the time. They were looking for a product manager to be the domain expert and help them build a simulator that closely resembles the operational system. I happened to be the right person in the right place. I interviewed and got the job. That was my first job in tech.

From there, I started exploring all the different things and functions. I taught myself programming. I went along to meetings with the sales manager. I sat around the engineers to see what they were up to. I built prototypes and dabbled with everything. While doing the engineering stuff was fun, challenging, and interesting, I found myself enjoying customer interactions more than anything else.

Fast forward a couple of positions later, I continued in product management for several years. While I was doing that at a company that did not have a fully-fledged marketing function, I proposed building the marketing function myself. I went to my CEO at the time after several years of being a product manager, and I said, “It’s time we build a complete marketing function, and I have the guy for you. I want to take on that job.” He agreed.

After I had hired and trained someone to replace me as the product manager, who happens to be the CEO of that company now, I moved on and became the first VP of Marketing. From there, I did rinse and repeat. I found myself at five different companies as the first marketer. I always sub twenty employees. That’s my sweet spot. I want to come in when there are a lot of things to figure out. I like scaling things that I build myself in those early stages.

I was fortunate to join five startups based in Israel selling globally. We took a couple of them public, got a couple of them acquired, and for the last several years, I’ve been with Gong, which is the third time I’ve worked with my CEO, Amit Bendov. I’ve worked with him at two previous companies over the last several years. When people ask me how I got this dream job, I say, “He called me and asked me if I’m able to help. I said yes. That’s how I got the job.” There are no heroic stories there. I’m building a good relationship and hopefully proving I was valuable in previous roles.

In the last several months, I’ve been the Chief Evangelist. I’ve passed the baton of managing the marketing team to an awesome new CMO that we hired, Brian. I am now focusing on lots of thought leadership and speaking opportunities like what we’re doing here. I’m running an influencer program. I’m taking executive alignment calls to show other executives how I use Gong as an executive myself and enjoying this new phase of my journey at Gong.

Thanks for that CliffNotes version. I’m sure there are lots of ups and downs in there, but something that caught my attention when I was looking up your LinkedIn profile is this interesting and intriguing title, which is Simulator Specialist. That’s what you’re referring to in building simulators for rocket technology.

That was what I was doing. I’m not a rocket scientist, but I am a rocket specialist. I couldn’t find a better title than simulator specialist. In hindsight, everything I was doing was a product management role. I was bringing the user knowledge and preferences to the engineering team and telling them what they should create. It looks to be like the real rocket system that they were simulating. I might go back and change that to product manager at some point, although simulator specialist is a little more intriguing.

It is a conversation starter. You’re simplifying and not giving yourself too much credit, but something that stands out if I or anyone else were to look at your career is how you pick and choose the right startups because that’s where the real formula is. What was your formula in picking those 3, 4, and 5 startups?

I’m happy to go into that. I had a few successes and less exciting choices that I made that I learned something from. The number one thing that I look for that has usually guided me in the right direction is the right leadership. If I had prior knowledge with the leader, like I did when I joined Gong, that would’ve been enough because this is the third time working with Amit. I’ve been working with him on and off for several years. I have well over several years of directly reporting to him. He’s the best leader and manager I’ve ever worked for. If tomorrow he went and started some not-for-profit social impact NGO, I’d probably join him there.

Leadership is where you can’t go wrong. The first time I went to work for him, I asked a mutual friend about him. He said, “You should go work for him because everyone who’s ever worked for him says wonderful things about him.” That was helpful. Do your due diligence on the leaders you’re going to work for. As a reminder, even if you’re in an early stage, fear the later stage in your career. You should be interviewing the company no less than they are interviewing you. If you’re going to commit most of your waking hours for the next several years to the company, it’d better be somewhere with people and a problem you enjoy working on. Hopefully, you are doing some good for the world.

B2B 56 | Leading Others To Success
Leading Others To Success: Leadership is where you can go wrong. So, do your due diligence on the leaders you will work for.


Leadership is number one by far. To generalize that a little bit, I’ve seen more success working with second-time founders or executives who’ve done some meaningful roles before the role that I worked for them. I’ve had some of my more questionable experiences with first-time founders who were young, never had a meaningful position, and what they thought was a great idea and wanted to build a company around it.

Sometimes, the idea was great. Sometimes, it was not great, but their people skills were green. They could be challenging to work with. You can expect that from a lot of first-time founders who have never built an organization and think that having great ideas is enough, but it turns out that the day-to-day job is a lot about motivating people, giving them a sense of purpose, hiring great people and continuing to build the company that way. That’s a little bit about leadership.

Two is looking for product market fit. This is a big one. As a marketer, I excel by having something to work with where there’s an initial product-market fit, and I can go scale that. As soon as we have a product that a certain group of people think is valuable, it solves a painful problem, and they have the budget and authority to buy that solution, I can bring lots more people like that. I’ll find the ways and build an image strategy, brand, and category if I need to. I’ll bring those people to buy the product. If we don’t have that minimum of initial product market fit, we don’t know who we’re selling to, and we don’t know what value we’re bringing them, how can marketing succeed?

I have seen failure both personally and with many talented marketers around me who come into a company without doing their diligence on product-market fit or maybe had a misleading picture of what that product-market fit looks like. We’re all bound to fail. Marketing cannot fix product market fit unless there’s a strong basis there. It’s clearly in marketing’s mandate. If you’re not a product person and you’re not looking to create the right product for the market, but you want to do the core marketing of creating demand gen and bringing people to buy that product, you’ve got to ensure that there’s early product market fit.

There are ways of getting hints of that. If it’s already a product with some sales and not an early stage, there should be reviews up on G2. There should be customer testimonials. You can ask to speak to a couple of customers and see how crucial the product is to their day-to-day, how they use it, and how happy they are with it.

If the product is terrible, people are probably writing bad reviews about it. If they love it, they are writing great reviews about it. You can ask to speak with investors of the company and see what got them excited about investing in that company. Speak to other employees and see what got them excited and what they were surprised about after they started working. Was it better, worse, or the same as what they thought it would be?

Do your diligence and make sure you know where you’re coming from because nothing is worse than leaving a job or celebrating a new job. Several months later, you are discovering things are not as you thought, not as you were told, and you wish you’d done that due diligence. It’s way easier to do it before than be surprised after. I talked about leadership and product market fit. I would also look, especially at times like this, at things like runway. Assuming this is an early-stage startup, it’s early to discuss profitability but understand what the sales trajectory is. If they haven’t started yet, yes, this may be a huge opportunity, but it’s also a huge risk.

If sales have started, what have they been? What’s the trend in the last several quarters? How much money have we raised? When do we need to raise more? How inclined are existing investors to give us more money? If we need new investors, what metrics are we coming up with that are going to get them excited about joining the company? All these are valid questions for anyone joining a startup. If you’re going to risk your best years, reputation, and livelihood for a company, they should be upfront with you about all these things.

Thank you so much for enlisting those. The three things, if I have to echo, first is around leadership, second is around product-market fit, and third is around the runway. I wish I had reached out to you earlier in my career because I didn’t do the due diligence. I know many others in my network who haven’t done that. That was one of the reasons why I prompted this topic, especially in this hard or even improving economic situation. People are still looking out there for new jobs. I want to give this piece of advice to you. Thank you for sharing that. On a lighter note, how do your family members, or even your friends, describe or view what you do in your corporate role?

I was looking at the question, and I was smiling because my husband would explain well what I did. My children, who are ages 8 and 10, would struggle a little bit. That says something about how difficult it is to explain marketing. It’s way easier to explain sales because even as children, they go and buy an ice cream. They understand what sales is, but marketing is a little bit more subtle and indirect. I’ve got eight-year-old twins and a ten-year-old. I heard one of my eight-year-olds being asked, “What does your dad do?” She said, “He works for a company.” That was her explanation. I thought that was sweet, but it also clearly indicates a failure on my part to articulate better what I would do.

This is something that brings me a lot of laughter, even for the guests. A lot of times, unknowingly, we get way serious and head down into our day-to-day jobs. It is those lighter moments, especially when we are with our family members. Quick pulse check and see how they view us and perceive us.

On a more serious note, beyond the nuances of the day-to-day work and explaining that to the children, I hope I’m modeling hard work as an ethic that I’m trying to instill in my children that no good things come easily in life. If they do come easy, they’re probably taken away easily. Working hard, but also setting boundaries for work time and family time, and knowing when to log off, put the phone aside, and enjoy family time, especially now that many of us are working from home. There’s more of an opportunity to practice that and model that for our children.

No good things come easily in life. If they do come easy, they will probably take away easily. Click To Tweet

I’m switching gears. I want to dive into two different aspects of your time at Gong. One is the early days when Amit reached out to you. You happily jumped and joined his team. That was the first phase, which is the early company-building phase and your role, what you are doing as a chief evangelist. Let’s talk about the first and walk us through. What is the thought process? How did you, Amit, and others go about finding the product market fit?

The product market fit was initially there. When Amit called me several years ago, he said, “Remember the crazy idea I told you several months ago?” I had coffee with him when we were working at two different companies. He left one company and said, “I’m going to start a company to solve this big problem that I had as a CEO where we had a quarter from hell. I didn’t understand what was happening. Looking at the dashboards, I could see what was happening but not why it was happening. I listened to a few calls, but I didn’t find anything systematic. I thought there must be a better way.”

He joined with a technical Cofounder, Eilon Reshef, our Chief Product Officer. They sat down to think about how they could solve this problem and provide more visibility to business leaders and revenue leaders on what’s happening. They thought that by collecting all these customer interactions, using AI way before it was cool several years ago, and analyzing them, they could surface insights that are actionable that would allow revenue teams to see what’s working, what’s not working, and change their behavior accordingly.

They build something basic. Nowadays, there are dozens of these call recorders. That’s how Gong started. We always had this big vision of how we’re going to help revenue teams. They rolled that out to twelve beta customers in late 2015 and early 2016. Several months later, they thought it was going well. They decided to check how serious these customers were.

They told them, “We’re going to shut off the beta in a few days. If you want to continue using this, you need to write us a check.” Eleven out of the twelve beta customers wrote a check. They didn’t want to shut it off. That’s when they knew that they had hit early product market fit. That’s when Amit called me, and he told me what I told you. He said, “I think we’re ready to market this outside of the friends and family. Can you come to help us?” That’s when I joined.

Did it take about six months from the idea to getting those early?

They started in mid-2015. By early 2016, they were in the markets. In several months, they had the first prototype out there.

We all know once we see the success story, 2020 is hindsight, but that’s typically the blueprint for successful high-growth startups. It’s all about customer validation and not hearsay but what you emphasize there. If I pull the plug on beta, are they ready to shell out money? Are they happy and okay with going away?

B2B 56 | Leading Others To Success
Leading Others To Success: The blueprint for successful high-growth startups is all about customer validation.


That goes back to what I said earlier about being obsessed with a problem and gradually building a solution to address it. We came out with the first solution that we thought would provide some relief from that problem. Once we got that validation, we kept building on top of it. Looking at some other companies where they tinker with the product and they build this whole house of cards over something that they don’t know how stable it is because they haven’t validated with the market, that can lead you down the wrong path.

We do something less drastic because the product is already out there. We’re not giving anything for free anymore. We’re not switching customers off when they can’t pay us. What we do now for new products and new capabilities is we survey customers and ask them on a scale of 1 to 5, how disappointed would you be if we took this away?

We’re not seriously taking it away, even though we do get some angry responses like, “Don’t you dare take this away because I need it.” It is always a good sign, but we want to see at least 40% of our users saying they would be disappointed or very disappointed if we took this away to know that we’ve hit product market fit. That’s a softer way of doing it rather than shutting it off unless they write a check.

You’re the Chief Evangelist at Gong. What does that entail?

Chief Evangelist is a unique role that I was able to put together with the help and support of Amit, my CEO. He used a great analogy when we started this process of adding new executives to Gong. In the last several months, we’ve hired a new chief revenue officer, a new chief marketing officer, and a new chief customer officer, and we’re on the hunt for a chief people officer.

The way Amit explained it to the company was when NASA sends a rocket to the moon, it’s not one rocket like that cute emoji that goes from Earth to the moon. It’s a multi-step rocket that the one piece gets us out to the edge of the atmosphere and falls off. Another piece ignites, and that gets us into the moon’s orbit. When that falls off, the final piece does a gentle landing on the moon. To get back, you’d need a different system.

There are few executives that have taken a company from zero to IPO, not in the CEO seat, but in the CMO and CRO seats, because you do need different people for different stages. I’m an early-stage marketer. I’ve joined five companies with sub twenty employees. I was always marketer number one. I’ve never inherited a team or a marketing operation. That’s where I thrive.

Speaking with other CMOs, I’ve realized that even going as far as I have. I’ve done the zero to tens of millions multiple times, but zero to $250 million as Gong, that’s rare. Most marketers are capped at zero to 50, 50 to 100, or 100 to 500, but zero to 250 ish is a long journey. It was time to bring in folks who have seen the hundreds of millions to billions part of the journey. Those are the people who joined Gong.

I carved out a new, fun role that takes on a lot of the things that I make the most impact with and also happen to enjoy. I mentioned speaking opportunities, thought leadership, running an influencer program, and executive alignment calls. I made that the core of my new role. I’m still making an impact without running a 60-person team. I don’t have an executive assistant anymore. I miss them all. I’m running my own calendar. I’m booking my own flights. I’m getting back to getting my hands dirty and doing work I enjoy without a lot of the red tape that comes with running a large team at a pretty large company.

You’ve shared a lot of insights over there. The most important thing that I took away, especially in the early days of the validation, plus your role as a VP of marketing and the CMO. What is the rationale for you and Amit to switch your role from being a CMO to a chief evangelist? The next segment is more around go-to-market success and a go-to-market failure story.

Before we jump into that, I was listening in and understanding your thought process. How did you build Gong? Even that famous show and talk of yours where you share the secrets around getting 4,000 plus leads from industry trade show. Something that I caught is first principles thinking. That’s the key if I were to convey your formula to others. Would you agree with that?

You’re putting it even more succinctly than I would, but many times, the success of go-to-market motions and marketing campaigns specifically is not about spending millions of dollars. I had a call with a CMO of a large company who wanted to learn about my experience with Super Bowl advertising. He told me, “It’s time for my company to build a larger brand. I saw what a great job you did with the Super Bowl. I want to learn more about that because I’m thinking of doing that.” I said, “I can tell you everything you want to know. I’ve done a couple of Super Bowl ads. I don’t think that’s what’s going to build your brand. It’s going back to the basics. It’s this ‘boring’ day-to-day demand gen stuff.”

It’s not boring, but it’s the stuff that doesn’t get headlines. People love to talk to me about the Super Bowl, and it was a nice cherry on top because 90% of what we were doing in demand gen at the time was working well. I could swing that budget and do an experiment that nobody knew if I was going to succeed or not.

In hindsight, it was fun. I’m glad we did it and elevated the brand a bit, but it was not a pivotal moment, at least not the way I see it in Gong’s brand building. It’s the day-to-day stuff. If you’re going to send an email campaign, and every marketer sends out an email campaign, and you don’t get the performance you want, you’re sitting there wondering what’s wrong, and you start throwing money at the problem. Let’s hire writers and do paid advertising. That’s not what’s going to save you. It’s looking at that email campaign hard and saying, “Would I want to consume this content? If not, why am I sending this out? Why do I expect anyone to read this if I wouldn’t read it? If this is pretended content that’s a thinly veiled sales pitch for my product, why would anyone want to read this?”

Thinking about, “How do you create content that is so good that you would want to consume it? If you want an even higher bar, how do you create such amazing content that people would want to pay you for it?” I know some people laugh and think that’s theoretical. Who would pay you for B2B content? When we created the Gong Labs articles, we would get, every few months, an email from an assistant professor at the University of Illinois, where they have sales courses. She would ask in the name of her professor, “How much would you charge us to license this material because we want to teach it in our university course?”

Another sales and enablement manager is excited about our content. She’s been passing it around internally. She wrote us asking how much it would cost her to license our material because she wants to use it in her official onboarding courses. We love hearing that because we know that we’ve hit that standard of creating content that is good. People are willing to pay for it. To avoid any doubt, we never charged a dime for it. We tell them, “Give us some credit from Gong, but use it as freely as you like because we’re not a content company. We’re a software company. We use content as a marketing investment.”

If your content is not hitting that bar, thinking that you can throw money at the problem is not going to fix it. It’s going back to basics. I like how you put it, Vijay. First principles, why would they open this email? Stop right there. Look at the subject line and look at the sender. Tell me why they would open an email that comes from Info@Acme.com or DoNotReply@SomeCompany.com. Why would anyone open that?

Think about all these little basic things. They don’t cost you money. They need you to switch your brain on and think as a consumer, not as a marketer because you have to rush a campaign out the door. As a consumer, why would I open it? Once you open it, why would I keep reading it? <Once you keep reading it, what would make me take action and click here to watch the webinar, download the white paper, or ask for a demo? If you can’t tell yourself a convincing story about why someone would be persuaded to do that, it’s not going to work. Don’t send it. Stop until you figure it out.

I can hear a lot of audience who go, and their main complaint would be, “You got things working for you, and that’s where you could invest that.” For them, it’ll be either the CEO, the marketing leader, or the sales leader saying, “Spin that next campaign and get those damn leads in.” On your behalf, I would go back and say, “Did you do your due diligence?” Going back to why you picked this job and why you picked this role, leadership, and product market fit. Have they worked on understanding the person and the problem?

Sometimes, multitasking leads to a lack of attention. If you’re trying to do five things at the same time, you’re not giving any of them the right attention to succeed, especially if you’re the first and only marketer or if you’ve got a small team. If you’re asking yourself and them to do many things, you’re not giving yourself a chance to succeed.

If you've got a small and ask them to do too many things, you're not giving yourself a chance to succeed. Click To Tweet

Cut down the number of things you’re doing and do a few things, and they will give you all the pipeline that you need rather than trying to spend money and do twenty half-baked things. None of them are going to work well enough. Focus on fewer things and get them right. Once you’ve got one right, you can scale that. It runs on almost autopilot. You can go figure out the second thing and the third thing. If you are trying to do 5 or 10 things at the same time, there’s almost no likelihood that you’ll get them right.

I’ve been studying similar to the NBA. We have 30 teams, but there’s something magical about those 1, 2, or 3 teams who make it to the playoffs consistently. It’s the same analogy that applies to marketers and CMOs. There’s something magical about those CMOs who’ve been on an ongoing basis. I’ve done research. It boils down to these three things. You can correct me and add to that, but it boils down to content, experiences/events, and community. If you layer one on top of another versus trying to do all 3 or 2 at the same time, that’s a magic formula.

There are variations on that. Some companies have succeeded without building a community. In hindsight, it took me time to realize that we had built a community, even though we never had that as a stated gold when we were putting out all this Gong Labs content. They have started forming a lot of conversation and discussion around it. The same people were commenting on the posts, sharing our articles, and showing up at our events. We created a community without calling it that and without labeling it as an effort to build a community.

We built such a huge following that not only is an audience for what we’re saying, but they’re also becoming ambassadors for what we do, speaking amongst them and arguing about what we’re doing, which is wonderful. The worst thing that can happen is that people ignore what you’re doing. If people are arguing and some of them hate it, that is a wonderful thing because that creates a conversation, and that’s what you want. If nobody’s commenting about your content or about what you’re doing, it’s boring. If nobody hates it, probably no one is excited about it either.

Let’s dive into a go-to-market success story and a failure story. You can pick outside of Gong Labs and the Super Bowl ad because people have heard that story so many times.

I’ve got many to pick from. I’ll pick a random one. A great story was when COVID started several years ago, and we were a few weeks ahead of going out for a road roadshow. We were going to hit 5 or 6 cities because we did a similar one six months earlier. It was a great success. We had everything lined up, booked, and dates, and the world shut down. We needed to decide what to do.

Many companies at the time decided to sit and wait. I don’t blame anyone. Sometimes, you don’t know what to do. You sit and wait because nobody knows how long this is going to happen. Are we going to be home for two weeks or two months? I don’t think anyone imagined it was going to be a few years. Nobody knew. We decided that being biased for action is almost always better than sitting and waiting. There are times when you need to sit and wait, but I’m personally not good at sitting and waiting. Ask my family. I’m much more biased toward action. Sometimes, I’ll take the wrong action, but I’ll take action. Most of the time, it works out well.

Here’s one way that our chief product officer puts it in other contexts. You can think of life as a series of decisions. Most of the decisions are a revolving door. If you realize you took the wrong turn, you can turn around, go back, and take another turn. Most of the life decisions are. There are few decisions that are past a point of no return. You make a decision, and you can never go back from it. There are few of those in life. Jumping off a cliff might be one of those, but we don’t often have to jump off cliffs. Deciding which marketing campaign to run is not one of those decisions.

B2B 56 | Leading Others To Success
Leading Others To Success: Think of life as a series of decisions. Most decisions are like a revolving door. If you realize you took the wrong turn, you can turn around, go back, and take another turn.


When everyone was sitting and waiting to decide what to do and see what happens, we decided, “We’re not going to skip a beat. If we said, in two weeks, we’re doing a roadshow, we’re going to do a roadshow, but we’re not going to do it in person because we can’t, the world is shut down. We’re going to switch to a virtual roadshow.”

I gave my team two weeks to figure out which platform we were going to use and how to run a virtual event. We’d never done that before. Let’s figure this out. We did it. For the first virtual event that we decided on two weeks before it happened, we had a thousand RSVPs, and a few hundred showed up for the live event. We went, “That’s more people that would’ve shown up to the combined road show that we were going to run. Let’s keep doing these and get better at them.” We did.

We got good at virtual events. The numbers eventually went up to multiple thousands of people joining an event and being amazed by the experience that we were able to provide them. We got to a point where we had an average attendee time at the event of over two and a half hours. We had some crazies who stayed for 6 and 7 hours because we were running a full day of events. Even during the lunch and bathroom breaks, we had live musicians, DJs, and magicians. It was like a three-ring circus to keep people excited. I could see them dancing and commenting nonstop in the chat. They were having the time of their life. It didn’t feel like a conference. It was like a party in their bedroom.

That was one of the many things that my team did well when we had to pivot very quickly and adapt to what was happening. The easiest thing to do, but the laziest thing, was to sit back, wait and see what happens. We decided, “No, we’re going to take bold action.” We might get it wrong. We spend a few thousand dollars on a virtual event that maybe won’t work, but if we get it right, we’re going to pioneer virtual events for our space. We’re going to get people excited before they get fatigued out of it, which happened a couple of years later. That was a story. I’m proud of what my team did there.

On the flip side, you’ve got type one decisions and type two. That is irreversible but always optimized for the reversible. Most of them it is reversible. On that note, what was a failure story and the lessons that you and your team took?

There are many failures to choose from. Anybody who only tells you about success stories, I would doubt their sincerity. We have lots of failures, but here’s one that I personally learned a lesson from, and this was also during COVID. This was in June or July of 2020. This is after the horrendous murder of George Floyd. It was in the rise of the Black Lives Matter Movement.

We had a quarterly campaign to run to collect reviews for a review site. We had done those campaigns a dozen times before, and we found that we could increase the participation rates if we offered folks a $25 gift card for Amazon or Target. Nothing ever went wrong with those campaigns. We have the idea of what if we try and do something good and we tell people, “We’d like you to write a review for us. We will gladly donate $25 to the Black Lives Matter organization for every review that you write us.”

We didn’t think this through. We felt intuitively that there was a little bit of sensitivity there, but we didn’t realize how much. We sent out the campaign to 6,000 people that we wanted to get their reviews from. Within an hour, I got half a dozen responses. It’s negative. People are writing to me personally, saying, “Udi, this does not look like a Gong campaign. I don’t know what you were thinking. If you want to donate money for a good cause, donate it. Don’t tie it in with something beneficial that you’re asking me to do for your company.”

I got a handful of those in the first hour. I had to make a decision, “What are we doing next?” You could make an argument that if I only got six responses. I pissed off six people, but I sent it out to 6,000 people. That’s one-tenth of a percent. It’s not a big deal, but I decided it is a big deal because my assumption was that for every person who took five minutes to write me an angry email, there are twenty people who are angry. They’re either too angry to write me because they don’t, they don’t care about improving me. They’re angry at me, or they couldn’t find the words or time to take the time. My assumption is if you’re getting a handful of bad feedback, there’s a lot more. They’re not writing.

Within an hour, I decided, “Here’s what we’re going to do. We’re going to send an apology email to all the 6,000 people that got the first email. It’s going to come from my name, owning the mistake and explaining what we’re going to do about it.” We immediately took all the budget that we had allocated for donating to Black Lives Matter. It was $5,000. We immediately donated it without waiting for a single review and letting people know that we’ve donated it. We apologize for the wording of the campaign that went out. It was insensitive on our part.

I sent out that campaign. Within an hour, I got 40 responses. All of them were positive, saying, “Thank you for owning up to that mistake. When we got your previous email, we knew something didn’t quite feel right, but we didn’t have the words to put a finger on it and tell you what was wrong with it. We’re glad that you figured it out and made it right.” That was an important lesson learned.

The two lessons, if to break it down, are one, be hypersensitive to social issues like that and do not do anything that could even be perceived through any lens as taking advantage of a painful situation to benefit your company. That’s one lesson learned. Two, if you do F up as we did, be quick to take ownership, make it right, and apologize. You’re going to get a lot more fans out of doing that than letting it drag out and see, “Let’s see how many people pissed off. If it was only six, it’s not a big deal.” We did the right thing. We got a lot of good karma points for doing that.

B2B 56 | Leading Others To Success
Leading Others To Success: If you make a mistake, be very quick to take ownership, make it right, and apologize.


It also talks to your leadership and as a person where you are being vulnerable in admitting your mistakes. That goes a long way where you’re creating that convenient or comfortable space for your team. It also shows that you’ve got a good pulse on your customers and audience.

That’s the way to do it. This story was a serious one, but we had other cases where we sent out an ugly typo in a subject line that went out to thousands of people. We also send out an apology email with a little joke in it, owning up to the spelling mistake. It was silly, and we’re all human. Why not admit it? People love doing business with other people who are real human beings and not just shiny brands that pretend that everything is always perfect because it’s not.

Something that comes across during our conversation is, as a marketing leader, a CMO, and a chief evangelist, you emphasize and focus a lot on content, demand, and brand. Something I’ve not heard a lot of is about product marketing. If I speak with a lot of founders and marketing leaders, it goes to 6 to 8 categories. You have the positioning and messaging, competitive intelligence, and sales enablement, especially if you’ve got a sales-led organization. You also have new market launch, new product launch, product adoption, and product content. There are more. What are your thoughts on the role of product marketing and go-to-market? What do you think are the challenge areas for Gong or others that you see in the industry?

Product marketing is the area that I’ve messed up more than any other area. At Gong, we did well with brand, creative, demand gen, comms, events, and content. We built some amazing things in ops. We did a lot of amazing things. In product marketing, I messed up multiple times. I got away with it for a long time because we had that early product market fit. Initially, it was easy to explain the value that we bring, to whom, what it does, why you need it, and why you should care. I didn’t have to build a strong product-market function.

When I did have to, I scrambled and made a few mishires that were good people who did not succeed for multiple reasons at Gong. That team is being rebuilt for a third time. I’m crossing my fingers. They get it in ways that I did not. With that disclaimer aside, the biggest role of product marketing is to tell the company story. You can break that down into company, platform, product, and competitive differentiation.

The biggest role of product marketing is to tell the company story, and you can break that down into company and platform and products and competitive differentiation. Click To Tweet

Gong went from being in a mostly non-competitive space for a long time, and we were the only player people were talking about, to a competitive space because the category that we envisioned all those years ago, we helped usher in as a reality. Everyone agrees that revenue intelligence is a must-have. It’s here to stay, and it’s not a question anymore. We have to shift our product marketing message from explaining why there’s a need for a category like that or what problem it solves. That’s been established. The needs are how we are different and better and why should you care about it compared to all the other solutions in the market. That’s the journey the product marketing is going through.

Product content has a role to play in positioning and messaging. Product adoption is a problem area, given how good the product is in itself.

We’ve been blessed with widespread adoption. Gong has over 4,000 customers and hundreds of thousands of users. The product is being used. That’s why I said it was easy for me to get away without great product marketing, for the most part, because the product did a lot of the work itself. A huge kudos and credit goes to our product and engineering teams that have built something truly incredible. None of my marketing success or my team’s marketing success would’ve been possible without the product that we were supporting.

It’s product content and sales enablement, given this new shift in the messaging. I know you have other things you need to get to in a busy workday. I have a few questions for you, Udi. Who are the 2 or 3 people that played a key role in your career growth?

Amit Bendov was a huge mentor to me in our previous jobs. That made me a candidate for my current job and the CMO job at Gong. I will always be in his debt for helping my career the way he did. Other people that I haven’t necessarily worked closely with, but resources that I keep going back to, are Robert Cialdini’s book Influence. I keep referring to it. Even though it was written in the ‘80s, it is still relevant as ever.

Everything that is happening now on social media and mediums that Robert never imagined in the 1980s is all built on the same principles of human persuasion and psychology. If you dig into those, and I’ve read dozens of books and topics, you’ll create better campaigns. You’ll understand consumer behavior and create better campaigns. That’s another huge resource.

One more is to understand market shifts. It’s a bit of a cliche now, but a good book is Geoffrey Moore’s Crossing the Chasm. It’s another classic from the ‘80s that explains how markets move and how your marketing, go-to-market, and product needs to change as you move from the innovators to the early adopters, to the early majority, and the later majority and the laggards.

B2B 56 | Leading Others To Success
Crossing the Chasm Marketing and Selling Disruptive Products to Mainstream Customers

What are the resources that you lean on? You mentioned books and people. I’ve seen your LinkedIn. You’re a big player in Pavilion and other go-to-market communities.

Now that we’re back into in-person meetings and communities, I’m enjoying leaning into some of the communities I belong to. One of them you mentioned is the Pavilion, which holds great events. We have small chapter dinners, larger events, and summits where I enjoy hanging out and meeting people who are friendly and helpful. None of us are pretending that everything is going perfectly. We can sit down and crack problems about team structure or certain parts of marketing that are becoming more difficult and hear how others are dealing with it. I try to go to a lot of those if I can.

I’m also fortunate to be an investor in GTMfund, which is run by Max Altschuler, Scott Barker, and Paul. We had a wonderful weekend offsite a few weeks ago in Napa. Eighty of us came together and had a wonderful weekend together, meeting people who are at similar stages as me in our careers and figuring out what’s next for them and how to balance their full-time jobs with investing and speaking. Doing other things was a huge resource for me.

If you don’t belong to a community that meets in person, that’s ideal. Depending on where you live, it might be hard. If you’re in a small town somewhere, you might have to start with a virtual community and hope they have a couple of in-person events that are even worth flying to. I would highly recommend finding an in-person peer community of like-minded people at similar career stages and functions as you go and share the day-to-day burdens. Even hearing from others about their difficulties and realizing that maybe things are not as bad as you thought for you is also a great relief that you can get from those communities.

Find an in-person peer community of like-minded people. Click To Tweet

I’m part of Peak Community, among other communities. I’ve seen you on the show with Sandra Malders.

I’ve spoken at Peak. That’s another great community there. There are many. There is the Product Marketing Alliance. I’m sure I’m going to offend a bunch of others if I keep going.

My point was not about, “You miss these communities.” It is more about the importance of being part of a community. The final question for you is, if you were to turn back the clock, what advice would you give to your younger self on day one of your go-to-market journey?

Become best friends with sales. That was a realization I came to way too late. Become best friends with your sales leader. You’re never going to succeed unless you do that. If you have this adversity or rivalry with sales and the finger-pointing and the blaming, why aren’t they following up on my leads? Why is marketing bringing crap leads? That’s not going to lead to success. You have to work like a two-headed dragon always together. You can’t win alone. If you try pointing fingers, you’re going to lose out. Become best friends with your sales leader. I’ve written an article about it and done some speaking on it. Welcome to Google Sales Marketing Alignment and my name. You’ll find some of my thoughts on that.

Thank you so much for your time and for sharing a lot of these insights. Once again, good luck to you and the team at Gong.

Thanks so much for having me, Vijay.


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B2B 55 | Rocket Lane

B2B 55 | Rocket Lane


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

Listen to the podcast here


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

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

Thanks for having me on.

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

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

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

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

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

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

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

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

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


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

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

It’s been a fun ride.

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

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

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

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

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

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

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


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

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

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

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

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

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

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

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

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


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

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

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

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

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

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

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

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

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

Many people don’t even think about it.

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

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

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

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


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

Was it a Zoom virtual or in-person session?

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

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

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

It was after the first 60 to 70 conversations.

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

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

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

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

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

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

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

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

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

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

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

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

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

Is this from your time at Konotor?

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

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

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

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

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

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

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

You should test out everything quickly. Click To Tweet

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Hire leaders faster.

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

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

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

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

Thanks so much, Vijay.


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B2B 54 | Category Design

B2B 54 | Category Design


If you want to specialize your business, this space will provide you with that path. Today’s guest is John Rougeux, an executive member at Pavilion and a partner at Category Design Advisors. From the failures to their success story, John brings us into the domain of category design and what they do in the market to help others become a dominant player. He also explains why CD matters and why its go-to market relies on word of mouth and referrals. Get to see how category design evolves in their space when you tune in to this episode. Don’t miss it!

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A Marketing Leader’s Journey In Category Design With John Rougeux

In this episode, I have another great guest and a conversation that’s coming up. I have with me John Rougeux who is the Partner at Category Design Advisors. Welcome to the show, John.

Thanks for having me, Vijay.

This is a go-to-market show and this is what it is all about so let’s start with that topic. How do you view and define the go-to-market?

I’ve always used a pretty simple definition. It’s the set of activities that you’re doing to get customers aware and excited about what you’re doing and turn that excitement into revenue.

That’s already a straightforward definition and view. I’m looking at your LinkedIn. You have been a marketing practitioner. You led and built marketing teams. In your capacity, you are working with various companies of all sizes. How do your clients perceive the go-to-market?

For some context, the types of clients that we work with tend to be ambitious startups. They’re companies that are either defining a new space for building a new category of themselves or participating in an emerging category where there’s no clear leader yet. They’re trying to improve their odds of dominating that space and being the go-to solution.

With that context in mind, a lot of what our customers have to do is educate the market on what they are doing, what problem they’re solving, why that problem needs to be solved, and what happens if it’s not solved. Use that as a wedge to then talk about their solution, why that matters, and why it’s categorically different from other things that buyers might have encountered already. It’s much different from a straight comparison type of situation where you stack up a bunch of features next to each other, specifications, or even pricing models. We’re talking about going deeper than that and talking about fundamental differences.

That’s one of the reasons why I’m super excited about this conversation. More often than not, especially when we talk about the go-to-market, the guests that I’ve had so far are like, “The founders are the go-to-market practitioners.” It’s typically around the go-to-market execution engine versus where you and I will be taking this conversation. We’re out to lean on you for your expertise and perspective is how to think about a category and how these go-to-market themes and go-to-market leaders can start thinking about category creation and enhancing their position in the category.

One of the myths that we try to bust is category design always means creating a brand-new category and being the first company to do that. Categories have a life cycle. They evolve. We’ve leaned on a lot of work by an author called Paul Geroski, who wrote a book happily titled The Evolution of New Markets, where he goes in-depth about this idea of categories evolving.

B2B 54 | Category Design
The Evolution of New Markets

I want to explain that and that’ll provide a good lens for thinking about how companies should compete in a category and what their category strategy should be. The research that Paul Geroski did follows as such. Before the category exists, what you have is an unsolved problem that exists in the world. Problems have to be experienced by people for them to be a real thing. You’ve got a group of people who are dealing with some problems and there’s no good solution for that.

Sometimes, this situation persists indefinitely. There’s a solution to these problems where we’ll never have a solution. That doesn’t constitute a category. It’s just a market opportunity if you like. What typically happens, though, is something will change. Maybe a new technology comes about or the problem gets worse enough to where people identify that it’s worth solving. Someone has an insight. They say, “I can build a solution that addresses this issue.” That’s when a startup is born or maybe a new venture within an existing company.

If that inside is valid, then you’ll typically see other companies latch onto that idea. They’ll come up with their attempt to develop a solution for that problem and group of people. In the early days, those solutions may look very different. One company solution might be viable and another company solution might not but they’re trying to experiment and get to a place where they’ve landed on the right solution for that issue.

As that process progresses, typically, what happens, as Geroski taught us, is one company has convinced the market that its design is the best suited for that problem. It’s what he calls the dominant design. When that happens, two interesting things happen next. One is that when customers see that there’s a go-to solution for this thing. They feel a lot more comfortable buying. You start to move from early adopters to more mainstream audiences because people don’t want to risk buying something that’s going to be obsolete, incompatible, or doesn’t work right. When they see that there’s a standardized solution, those barriers come down and the purchase becomes a lot less risky.

When that happens, the company that’s established that dominant design tends to dominate that space. The other players in that market have to either come along with that or exit the category. When that dominant player comes into play, the market cap of the category grows and the number of competitors decreases. I’m trying to condense a couple of hundred pages of that idea into a few minutes. We would like to understand where your category is in its evolution. It’s important for you to figure out what kind of strategy you need to set for yourself.

The company that has established that dominant design dominates that space and the other players in that market. Click To Tweet

Thank you for setting the context and the thought process behind the whole concept of category in the first place. Before we dive deeper into this topic, let’s unwind a bit over here. For me, it’s all about understanding why did you decide to go into this space. What motivated you? In that context, if you can share your career story? What led you to what you’re doing?

The quickest way I can describe it is if you’re a marketer and you’re trying to bring a radically new idea to life using the traditional playbook of capturing market share, your life is hard. That was the journey that I experienced. I spent some time at some early-stage startups early in my career. I was a cofounder of one of them. We were solving problems that didn’t exist before and had some different ideas about how to solve them.

We had some initial traction but everything I’d been taught to that point was how you compete against competitors and differentiate yourself but it’s always in the context of other companies. I started to explore other ways of going about marketing. That led me to business strategy and then discover category design as the framework for bringing new things out to the market.

You did leave an equally exciting part of your journey, which is your backpacker way back. What is that like?

My wife and I decided to hike the entire Appalachian Trail together. We had our first anniversary while we were backpacking. It was that early on. It’s about six months of backpacking solid. It was a lot of fun. It’s much more of a mental challenge than a physical one.

You didn’t go into the tech industry right away but eventually, after a couple of roles, you did move and take the industry and marketing function. You were a CMO. You were a host on the B2B Growth Show. I was not aware of this. I’m an avid listener. That’s fantastic. You went into a marketing leadership role and also were building a marketing strategy at BombBomb, which is similar to video marketing or video sales tools. It falls somewhere in that category.

The broad space is like video messaging. You put a label on it.

Here you are at Category Design Advisors. You did share that journey. What prompted you to make that radical shift? You did touch upon that. In a nutshell, you did mention what you’re doing and how we were taught what you need to do as a marketing leader. It was not paying off or did not die in the right way. Expand on that. That’s a very critical insight that we should dive into.

To go into that a little bit deeper, I didn’t find any good framework for taking something that people aren’t familiar with at all and don’t have any context for. We’re talking to them about that in a way that matters to them and shows why this new business needs to exist. A lot of what I was learning at the time was very tactical, like how to get more traffic to your blog, how you optimize an ad campaign or conversion rate on a landing page, or what the best practices for marketing automation are, tactics that are good but can only move the needle so far if you don’t have the fundamentals correct.

In one of the businesses that I worked for, we were developing a way for local businesses to generate word of mouth on social media. This is in the early 2010s when social media was in a different state than it is in the present. Looking back, I realized that a lot of our customers came through word of mouth and opportunities where we could be on the stage or a show and share the narrative and the story behind what we were trying to do.

One of my cofounders built a product for himself. He was addressing an issue that he faced. Other businesses latched on to that because they were going through a similar situation. When we removed that ability to tell that story and convey that narrative, it was very difficult for us to drive business. That puts a cap on our growth because all those tactics I describe like the conversion rate, optimization, this and that, and the other, don’t address the real issue. I was curious. I said, “How did people go about building businesses before digital marketing?” You couldn’t use paid social and things like that.

When we remove our ability to tell that story and convey that narrative, it's difficult for us to drive business and it puts a cap on our growth. Click To Tweet

One of the books I encountered in the process was The 22 Immutable Laws of Marketing by Jack Trout and Positioning by the same authors. Law number one is to be first in the category. Number two is if you can’t be first, set up a new category that you can be first in. That idea was foreign to me. I was talking to a friend of mine, James Carbary. He runs Sweet Fish Media, the company that runs B2B Growth. He said, “If you like that idea, you should check out this book. It’s called Play Bigger.”

B2B 54 | Category Design
The 22 Immutable Laws of Marketing: Violate Them at Your Own Risk!

This is about 2017 or so. The book was only about a year old at that point. When I read that book, I immediately knew that if I had this framework a few years ago, it would have dramatically changed our trajectory and our ability to grow the business. From there, I started to apply this thinking within the companies where I was working. I did some things that worked. I learned some things that didn’t work and made some mistakes because this was a very new discipline at the time.

What I realized though was I enjoyed the discipline. I started doing some consulting on the side and helping some early-stage founders through the process and found that I was adding some value and wanted to work towards doing this work full-time. I developed a relationship with Christopher Lochhead. He’s been a great mentor of mine. I ended up getting to know my partners at CDA and we started working together full-time.

Play Bigger is one of those books especially for founders and go-to-market leaders who are thinking about building big markets and number one position in the industry. Play Bigger is a must-read for those people. You read the book. Essentially, you connected with that mindset and the principles that are stated in that book. You were a mentor and in touch with Christopher Lochhead, who is one of the co-authors.

When I started the B2B Growth Show, it was my friend James. He challenged me. He said, “John, I know you know very little about category design. Go start a series on my show about it.” He was the first person to interview Christopher Lochhead.

What is the hook? How did you manage to get Christopher on the show?

I asked him just like you asked me.

Let’s get deeper into what is CDA. What do you folks do? What is your go-to-market?

Our go-to-market is pretty reliant on word of mouth and referrals. Frankly, it’s different than probably how our customers operate but we’re pretty selective on the number of clients that we work with in a given year. We’ve done closing on 45 engagements with companies over the years. We’ll do 6 or 8 a year around networks and the content we’re producing. Kevin, the co-author of Play Bigger, brings a lot of credibility and interest to what we’re doing. It’s not super complicated. Build relationships with good people, produce content that adds value to people, and the rest pretty much follow suit.

I’m on the website. I was looking at projects and engagements that you do with these companies. It’s very impressive. You folks work from early-stage startups to pre-IPO and even companies that are public enterprises. As a startup, it’s a big panda. That’s one of the case studies that you have in there. Your pre-IPO is Sprinklr, and then companies that are big and large like LinkedIn. It’s a very impressive roster. For each of those stages, what is the need? What is driving them to engage you folks in their go-to-market?

I mentioned the word ambitious and that’s a good word to capture how our clients are acting. If you think about athletes in the Olympics and they’re 4th or 5th in the world, their goal is to be that gold medalist. They will invest every resource they have to make that happen. That’s how our clients are thinking there. They have their ambitions set on not just bringing something new to life and establishing a new space but dominating that space and emerging as the equivalent of the Salesforce as that space matures. That’s why they’re bringing us in to help them realize that goal and improve the odds of being that dominant player.

When you talk about category design and when I start reading more into the concepts on Play Bigger, the first story that all of us, including the readers can relate to is, what Marc Benioff did with Salesforce. That was a huge eye-opener. For the benefit of those readers who are not aware of the story, which should be the minority of this, Marc Benioff came out from Oracle and Sable in the CRM space. He realized, “All of those were perpetual licenses versus why should anyone even own a license. Kill the software concept and have software releases and improvements daily word. You don’t have to worry about the maintenance of the software as such.

We take it for granted that that’s the normal way of doing things. At the time, I remember the Wall Street analysts didn’t even know how to value their revenue because it was all this recurring revenue model, which was foreign to them.

He’s shifted how all the software companies have to think about and go-to-market with this new concept and business model. That’s a classic example. For the readers who are not aware of category design, connect with the story of what Marc Benioff did with Salesforce. That’s the entry point. Thank you for sharing that context.

It was super helpful to why category matters and coming back to the keyword that you mentioned, how the ambitious founders and go-to-market leaders should think about and why they should pursue category design or category creation. With that as a context, it’ll be helpful if you can share with our readers a go-to-market success story and failure story around the category.

The way that I’ll describe it won’t be around the go-to-market mechanics and the things that a CRO or a CMO might cover. The way we look at it is if you get your fundamentals around your category straight as you write, then whatever go-to-market engine you build has a much greater chance of being successful. Whereas if you have some misses on your category strategy, then you might have the most finely tuned GTM engine in the world but it’s not going to get you where you need to go.

Why don’t I start with a failure first because that makes success a little easier to describe? One of the things that we try to look at when we help a client develop their category strategy is focusing on the problem that they’re solving and making sure that it’s a valid problem, the problem causes enough pain, and enough people are experiencing it. In other words, it needs to be a problem worth solving.

That sounds obvious. Why would you build a company around a problem that you hadn’t validated? This happens all the time. I’ll share a pretty high-profile example. There was a company called Quibi. They made a valid observation initially. It was that people were consuming more media on their phones while they were on the go. That’s a valid insight. They took that idea and built a whole company around this notion, like a mobile-first video platform.

In case you’re not familiar with them, the idea was that they would create original content. The content would be very suited to this on-the-go-on-my-phone type of behavior. Episodes were about ten minutes long. They had this interesting technology where you could rotate the phone and the video would look good in portrait or landscape mode.

They have some smart people. Jeffrey Katzenberg and Meg Whitman were two of their big investors or board members. They raised $3,750,000,000. They had a huge marketing campaign. Retrospect is so easy to see but the miss was that there was already a pretty good solution to the problem identified and it’s called TikTok and YouTube. They weren’t providing enough of an incremental benefit to be worth paying a whole other subscription to. On top of that, I’ve heard their content was pretty bad so that didn’t help but even if their content was decent, they would have run into all the same issues.

The company folded within a year and a half of being launched. This is a great example of a company not understanding that this category of mobile or first video platforms was already pretty well established. There were already some pretty good options there. They’re trying to come in, redefine that, and dominate in a way that didn’t provide orders of magnitude of benefits. It’s a losing proposition. No amount of money, advertising, or marketing could save them.

That’s a failure. I can share a success. It’s one I didn’t work on myself. I don’t want to take credit for it but my partners Dampen and Kevin did. They work with a company called Sprinklr. For some background, Sprinklr broadly plays in the customer experience space. There are already some established players there. Call tricks are one. The way they are perceived in the market was they were another me-too customer experience tool, of which there were dozens.

At the same time, their CEO knew that they had something different and they were building something special but the market couldn’t see that. We have a term for that. We call it Category Jail. It’s when the market misses mentally and miscategorizes what you do. What they did was use the category design process to build a narrative that captured what they were doing as categorically different and set the stage for them to build on a different trajectory going forward.

They call it unified Customer Experience Management or unified CXM. It was more than just a label, though. It was a way to identify all the problems that happen when you use a hodgepodge of point solutions and try to cobble them together. There are all sorts of gaps that still happen in the customer experience when you do that. That was an aspect of the problem they honed in on.

They went through that exercise right before their IPO. When they did that, it changed the way that investors perceived them. It went from a me-too solution to, “This is something different.” They not only have a different take on what they’re doing but the opportunity is much greater because this isn’t just another set of point tools. Their IPO is successful.

They’re a multibillion-dollar company. Making that IPO successful for them was key. That’s an example of the end stage. That same process still unfolds whether you’re at series C or even if you’re very early on. If investors don’t see why you matter, they miscategorize what you’re doing. They’re either not going to invest or undervalue you, and you want to get the valuation you deserve.

That’s a great story, for sure, especially the term. Customer experience management is so overly used. A lot of the CRM companies are positioning themselves as CXMs. The cool story about Sprinklr positions itself as CXM but it looks like a niche within a unified CXM. That’s what sets them apart. Once the market and the investors see the story and see them as a player in a much bigger or different category than the existing players, the valuation will go up, and that will show up in their stock price.

The takeaway is that when you do category design well, you are controlling the narrative. You’re not using a narrative set by somebody else or building your narrative around points of comparison to other tools.

Two questions that come to my mind from that success story. At what point in time is it right for the founders and the leadership team to think about category creation and category design?

The answer is day zero. What the process looks like for a very early-stage company, a couple of guys in a credit card versus pre-IPO, is different. We did an interview with Craig Rosenberg on Scale Venture Partners on our show. This is one of the things we were talking about. When you’re in the formation stages of the company, picking a problem that no one else has addressed or a radically different approach to a problem that is far different from the status quo is very powerful in terms of creating a business that can do something meaningful and can get people excited about them.

When I say the process looks different, there’s a lot more conviction you have toward the tail end around what that solution looks like and what partnerships and the whole ecosystem might look like. You’re putting those thoughts into stone at that point and pushing hard into the market about specific language you’ve built and specific aspects of what this category needs to look like.

When you’re early on, you have some hypotheses around this problem. You’re trying to validate your ideas as quickly as possible. You might have a good handle on the problem. Your solution might be wrong and you’ve got to iterate on that. You’re more like writing in pencil but still going through the process and thinking about the problem first and the solution second is something every early-stage company should be doing in my mind.

It’s easier said than done. In the early days, the founders and investors were all like, “How quickly can we get from problem validation to product market fit?” The path that they take to get to that point may not necessarily be thinking about category creation or educating a market about a new category or product that they should invest in and buy at this point.

If you do it right and you can show people that there’s a problem that hasn’t been sold, that’s a very powerful way to gain traction. The other path you have to take is you’re competing in a space that’s already established. You’re trying to come up with a better, cheaper, or faster solution or maybe have a niche that you can serve better than someone else. I’m not saying you can’t do that but that’s not an easy path either.

If you do what you're doing right and show people there's a problem that hasn't been sold, that's a powerful way to gain traction. Click To Tweet

The second question that came to my mind when you were sharing the GTM success story is slightly controversial but interesting. I’m sure it must have been debated a whole lot. There were mobile phones even before Apple came out with their iPhones. It was an established market and category. What did they do? Everyone knows what they did. They didn’t have to create a new category but they’re leaders by a far distance in the smartphone category.

Do you remember when we were talking about the evolution of categories and had played over time? At that point in time, the dominant design was the Blackberry. The Blackberry was more geared toward business users. It wasn’t something that your grandma would buy. There was still this unmet need of people wanting to browse the internet and people wanting to listen to music on their mobile devices to make phone calls and texts on a single device. The Blackberry wasn’t suited for that for the market at large. It was a good dominant design for that niche business user space but it didn’t address what the broader world needed.

B2B 54 | Category Design
Category Design: The Blackberry wasn’t suited for the market at large. It was a good dominant design for that niche business user space.


Apple was a genius at understanding the problems that people had with the way Blackberry worked and traditional mobile phones or things they couldn’t do. They use that to inform what this new design or this new take on a smartphone should look like. As you know, that is established as the dominant design. Even if you have an Android phone, it still has a similar industrial design. It still has an app store, which is a key component of that dominant design. It still works and feels the same way as an iPhone.

The main takeaway is the point that you mentioned early on, which is the category evolution. Apple was the first player in that category evolution like step zero. They created a whole new bump in the category. It’s just not the business users of the Blackberry users. Now, it’s a much larger market. They’ve expanded the market a whole lot and they are one leader.

They didn’t create this smartphone category but they designed it in their favor and expanded what that category represented into something much larger.

I appreciate the insights and the thought process around category design, category creation, and category evolution. Switching gears, coming back to more of the story behind John. What are 1 or 2 skills you are known for in the industry of the market? When someone thinks, “I’m struggling with design. I need somebody to talk about this so I should reach out to John,” what are those 1 or 2 topics that people reach out to you for?

As category designers, what we tend to be good at is critical thinking and assessing things more objectively. I’ve run into this challenge myself. It’s very easy to lose sight of the forest for the trees when you’re in a startup or even any company. When you’re so close to it, you can’t see things objectively. Our ability to look at things dispassionately and assess what needs to happen from a business perspective is something that we find tuned pretty well over time.

It's easy to lose sight of the forest for the trees when you're in a startup. Click To Tweet

Instead of talking about me, let me talk about one of my partners, Kevin Maney. He’s arguably one of the best people in the world at articulating difficult-to-explain technology in a way that everybody can understand. Jeff Bezos used to even call on Kevin to help him unpack some ideas he was thinking about. I’m lucky to work with someone like him.

It’s not very often that many people get a chance to work with such industry thought leaders or category creators in this case. I’m sure you must be excited and grateful to be working with Kevin and others at CDA.

It’s a good group. There’s a lot of fun.

The other question that keeps coming up is, what are the resources or the exciting topics that you research or lean on? You mentioned the fact that you host a podcast. You must be listening to other podcasts and reading books, I’m sure. What are the other resources that you lean on or people you lean on?

I read a lot of things that are not pure marketing or pure business books because I like to get inspiration from unexpected places. One of the books that I’ve read a couple of times is called The 33 Strategies of War by Robert Greene. It’s pretty dense. It’s not like a bedtime story or anything. He uses a lot of historical examples to talk about how different countries or militaries have engaged with each other. Many times, he explores the dynamics of different competitions, which is useful when you think about businesses and how they interact. That’s one.

We have a community that we started called Category Thinkers. It’s about 600 folks in there who are all thinking about or working on category design in one capacity or another. That’s a great place for us to fuel our thinking as a group. I’d like to share what I’ve learned. I learned things from other people from other corners who are thought of as something I haven’t discovered. That group dynamic and community have been valuable too.

I recall you saying about that community. I did join. If I did not, I’d be part of that. It’s cool to understand. More than coolness but it’s about how other people are thinking about category when it comes to that go-to-market. That’s my perspective and what I’m curious about. We’re going to be part of that. Shout-out to that group. For the readers, join that group.

If you’re not there, let me know when you join. I’ll make sure I say hello to you when you pop in.

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

Look for input from others more readily. One of the mistakes I made was thinking I knew more than I did and not knowing what I didn’t know. You can only discover that by getting perspective and feedback from other people. I would have been even more proactive about reaching out and finding people who were ahead of me or came from different disciplines who could share a perspective that I didn’t have.

B2B 54 | Category Design
Category Design: Reach out and find people ahead of you or from different disciplines who could share a perspective you don’t have.


Thanks for sharing that. That’s something that I grew up with as well, almost on a daily basis. More often than not, we think that we know and we have to be sure. We are confident. We believe that this is what it is, what my stands are, and what I will be doing. I wish I started earlier in building that personal board of advisors and having them as a sounding board or even giving them the comfort and the luxury of saying, “Vijay, you’re wrong. You’re going to screw up on this.” Creating that space is important. Thank you so much for a wonderful conversation, John. Good luck to you and the team at CDA. We’ll be rooting for your successes.

Thanks for having me, Vijay. It was a real pleasure.


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B2B 53 | Aligned

B2B 53 | Aligned


Success in today’s market isn’t about rigid plans, but the ability to adapt and evolve your go-to-market strategy. Our special guest, Gal Aga, co-founder of Aligned, shares his experiences, challenges, and successes in building effective GTM strategies that adapt to changing markets. Gal emphasizes the importance of understanding your Ideal Customer Profile (ICP) and why it’s crucial to niche down before expanding. He further explains how this laser-focused approach can unlock doors to previously untapped markets and foster rapid growth. Discover how Gal moved from traditional direct sales to product-led growth (PLG) at Aligned and the transformative power of shifting strategies in response to market dynamics. In this transition, Gal proves how it requires a flexible mindset and the willingness to unlearn and relearn. So, if you’re navigating the turbulent waters of go-to-market strategies or seeking to redefine your approach, this episode is your compass. Tune in now!

Listen to the podcast here


The Aligned Approach: Secrets To Navigating Complex Sales Motions With Gal Aga

Welcome to this episode of the show. Thank you so much for taking the time to tune in to yet another episode, or maybe it’s your first episode. My sincere thanks for that. I have the pleasure of hosting another founder. This time, it’s an Israeli-based startup founder. His name is Gal Aga, and he is based in Israel and is the Founder of Aligned. I’m sure we will dive a lot into his go-to-market thinking and go-to-market approach. With that, welcome to the show, Gal.

Thanks so much. I am excited to be here. Go-to-market is one of the most interesting and close-to-heart topics, so I am very excited to discuss it.

I feel the same here. That’s why you are on this show. I am super excited for that. With that, how do you view and define go-to-market?

It’s one of these things that there are a lot of different versions out there. When you go and start building one, a lot of people put a lot of things into the mix. For me, it’s on a high level first. It’s a strategy or blueprint of how you deliver your product or service to your end users. It involves all of the different elements around it. From who is the buyer persona, which targets or which markets are you targeting, the ICP, competition, your sales motion or sales strategy, how you are going to promote the product, whether you are going to market it, and the pricing element. That’s how I have done it in the past.

It involves all of those things. You did mention about the different functions that you need to work with internally. That’s the product you start with, and then there’s marketing and sales. If you are a SaaS business, there’s the customer success element, which is the wholesale aspect as well. I know you are implicitly referring to it, but at the end of the beginning, it always starts with the buyer and the customer in mind in the go-to-market.

The best ones and the clearer ones that I have seen have always started with the buyer persona, defining all these different people. There is more than one. There’s the decision maker. Who’s the potential champion? Who’s the economic buyer? What are they, buyer persona or end users? From there, it’s easier to build the rest of it.

There is a whole ideal customer profile. It goes at the account level as well as the different stakeholders at the account level and so on, which I’m sure we will dive more into our conversation going forward. This is a great start. Let’s take a step back. Why don’t you tell our audience about your career story exactly why and what got you to the point in starting your startup and what you are doing?

I was fortunate to find my passion early on, which was in sales, and then, at some point, building go-to-market teams or revenue teams. It was then more to the wider scope of go-to-market. I have been in SaaS B2B sales for several years. I took the path from AE to sales manager, sales director, head of sales, VP, and CRO.

I have built. I love building. I was typically very involved early on when you need a lot of methodologies and hands-on strategy. I love building playbooks and go-to-market decks. I have done that multiple times. I had the opportunity to be involved in taking the company from the early stage of $1 million to $10 million. At some point, I also did the $20 million to $100 million range. I was very curious to see how that would work. I started in a telco sales, selling telecommunication technology.

That was Orange Telecom?

Yeah. It was a huge school. I started from the basics. It was before SaaS was something that people even were talking about. I fell in love with sales there and started researching and saying, “I want to build a career there.” There were these superstar sellers there that were selling the more strategic telco equipment. I remember seeing how they were selling, how much they were earning, and the potential.

I started researching and found this thing called SaaS. I researched SaaS and started my way there. My company very quickly understood that this is where I want to be, self-learning all of the insight sales methodologies and all of the SaaS methodologies. At that time, the CEO saw the potential and promoted me to head of sales.

I did, at that point, the decision to go back to selling after building. That was very early. I was building a sales organization myself. I went back to selling and did the enterprise AE path. I wanted to learn from experts. I found someone, a mentor. From there, I went from the sales director, VP sales, CRO, and Aligned. What brought me to found my own company is I knew that it was going to come at some point. Leading, finding more challenges, and doing more things have been my big passion. The opportunity came very early on. I had a passion for sales, so everything got connected. That’s where I am.

You are lucky in so many ways that you found your interest and passion to be in sales from day one of your career. Not many are fortunate. Kudos to you for realizing that and then making the bold steps to seek mentors and create self-learning paths inside sales as well as whom you want to work with. You were even going down the ladder so that you could grow up exponentially in a sales career and sales path. You have done that.

There’s always the notion. It’s not so much where sales or a salesman and salesperson has a very negative stigma, especially if you think of a card salesperson. That’s not the case. We all know that, especially for those who are in the industry. I’m curious. How do your family or your friends describe what you do at work?

The first thing that comes to mind is my son. I love Tesla. I am an Elon Musk fan. I was talking with him a lot about Tesla. He is interested in Tesla. He chatted with me a lot about the potential and the idea. At some point, I explained in one of the chats about the stock market. He describes to his friends, “My dad is Gal Musk.” My son already knows how to say it, but I’m far away from it. Hopefully, one day, I will come close.

It’s interesting how the kids perceive and what type of monikers they bring or gives to the parents when they learn what they are doing at work. Coming back to Aligned, you started Aligned clearly because you were motivated by what you have done in sales. There have also been the gaps that you started seeing while growing up in a sales career. What is Aligned about? What are you trying to solve and for whom?

Aligned is a customer collaboration platform that helps revenue teams better manage the complexity of their deals and their customer success projects. Think about a typical sales process or onboarding process where you have more than 1 or 2 calls to close that is not very transactional. Your customers are juggling a lot of different email threads, e-links, attachments, and tools you can get to mutual action plans in a spreadsheet.

B2B 53 | Aligned
Aligned: Align is a customer collaboration platform that helps revenue teams better manage the complexity of their deals and their customer success projects.


There are a lot of these different things all in attempts to go and enable a champion to sell for you internally or to enable multiple people to get what you do or get your offer. It brings all of these elements into a single collaborative customer-facing workspace where you can centralize all resources, mutual action plans, and key discussions with the customer.

It is a single link instead of all of that back and forth. Everyone involved in the deal can stay on top of the next steps and timelines. Stakeholders always have everything in front of them. It helps your champions sell free internally when you are not in the room. It helps sellers access more stakeholders. It helps keep onboarding or a sales process on track. It helps your action plans. It helps you sell smarter by also analyzing buying behavior in that workspace. That’s pretty much it. Overall, it reduces churn and closes more deals faster.

What prompted you to come up with or pursue this idea in the first place? Why this?

Specifically in my sales career, I have focused on the complex selling motions more like mid-market sales or getting a new startup off the ground, pioneering into a new category where you need to do a lot of why do anything, why ask stuff, excelling, and challenging. One of the cofounders, also named Gal, used to work together at the same company called Syte. It was a very complex sales motion to the retail tech.

We were hiring AEs. I was seeing all the time in my mind what makes a difference between the top sellers and the rest. It was a huge difference. The top sellers were doing $500,000 deals and $700,000 a quarter. Most of the reps were either 70% of target or some of them hitting $100,000. It was a huge difference. I remember one of the reps was closing a deal. She was doing a lot of things in that deal where she wasn’t selling. That was the a-ha moment. We saw that she was not selling. She was curating a buying experience and making it easy for the champion to sell for her while she was not there.

It was all about educating and bringing success criteria formats, building decks, putting in the decks throughout the process in a lot of the next steps and timelines, and updating the decks. She was summarizing all the time the next steps over email. She was creating a mutual action plan over email. A lot of the time, email summaries that mutual action plan.

We saw that, and a few years later, Gal opened a line together with Yotam, our third cofounder and CTO. He always had that dream to open after Syte. I was a CRO at that time. When they started Aligned or started thinking about the idea, he brought me as an advisor. We look back and remember that we knew we wanted to do something in sales. We looked back at these experiences and said, “That’s it.” We researched it more and saw that buying is getting more complex. Buyers are shifting away more from the seller. Gartner is writing about this all the time. Only 5% of the buying journey is spent with the seller. Meaning, most of the time, sales happen when you are not there in the room during the sale.

When we look at how selling happens, it has not changed for years. The sales stack is bloated, but the actual selling and execution of the deal, not emailing and getting pipeline. The actual deal management is still PDF, PowerPoint, or Excel while you have Miro workspace, Slack, Notion, Figma, and workspaces for collaboration in every other area of this. That is the inspiration and motivation. That’s the long version of the story.

The term that caught my attention and which should resonate, and maybe you should use it in your positioning and messaging if you are not already, is curating a buying experience. That’s key. You revealed the playbook of top sellers. That lady was not selling but made it easy for the internal champion to “sell internally” on her back.

That’s what it’s all about. With the budget scrutiny and especially everything that’s going on, if you are not doing that, it’s so easy to choose the status quo. It is so easy for the CFO to challenge your business case when you, as a champion, go there. If you have not been enabled throughout the process, if you don’t know the answers to everything, and if someone didn’t support you, you are going to get stuck as a buyer.

B2B 53 | Aligned
Aligned: If you don’t know the answers to everything, if someone really doesn’t support you, you’re going to get stuck as a buyer.


That’s the origin of Aligned. We all know that developing the product and having a hypothesis is one thing. How was the early days? I believe the company was incorporated in 2021 or 2020, depending on where you look at all the legal aspects and things like that. How were the early days? What is the hypothesis around the ICP? How has that evolved?

In the early days, we made a mistake there. We were thinking already too long-term. We were saying, “This is going to take all over the world. This is CRM level category,” which we still believe it is. We can have CRM level scale, but we were saying a little bit at the beginning, “Anyone that’s selling should be able to use this.” At some point, we understood that the beauty is in going a bit more niche at the beginning and tailoring and doubling down on targeting. We optimized it to not be any B2B, but B2B tech. B2B tech is probably going to have higher complexity in the sale process or early adopters of tools.

Secondly, we were defining what complexity is, so anyone that has more than 1, 2, or 3 touches to close. There has to be either a lot of stakeholders to manage, a deep process like a POC to manage, and a deep onboarding or long onboarding. It could even be a pretty transactional sales process with a lot of content sharing because of a lot of education and enablement. That’s where we narrowed down the ICP.

Your sales team or outbound team is focusing on these in the discovery call and prospecting.

That’s correct.

Let’s go back to our conversation earlier in the show, which is the definition of the ICP and how that has to constantly evolve as you evolve your go-to-market. Thanks for sharing your lessons on how you evolved your ICP for Aligned. Coming back to some of the growth aspects and the growth story around Aligned. Feel comfortable to share only what you can share in a public forum. How has Aligned evolved or grown in terms of funding and fundraising the number of customers, revenue, and even the number of employees?

We closed our seed round in the craziness of 2022. It was July or August 2022. We founded the company in October 2021. We did initially a pre-seed almost a year later. We closed the seed round, and when we closed the seed round, we already had the signed partners and initial revenue. From there, we, a year and a little bit after that, have been growing between 50% to 100% quarter-to-quarter.

I can’t share everything, but we are, at the moment, 17 employees around 10,000 users of the product, and around 150 paying customers. That includes also free users in the freemium. Aligned has actual two go-to-market motions. One is product-led and the other is direct sales. That’s one of the biggest challenges to get off the ground with the product with that go-to-market because you are constantly building both. One is for optimizing. These are the high-level details. Was there anything else that I missed?

You did cover the funding, the number of customers, and the number of both the free trial and the paid user. I appreciate that. You did cover the number of employees as well. That’s fine for a public forum. I understand that. Let’s get into the go-to-market success and the go-to-market failure story. You have seen both. I would like to understand your thought process around how you are managing product-led growth like PQLs, MQLs, SQLs, and so on. That’d be good to dive into as well.

I can start giving a high-level about that first. It’s even three motions. It’s PLG, PLS, and direct sales. I have built three sales go-to markets in the past. The sales part involves the product. It involves a lot of marketing within it. This is the most complex that I have done. When you nail all of them together, they are very powerful. For PLS, a lot of people don’t know that term. It’s Product-Led Sales. That means that it’s not only free users who are converting on their own, but you are using the free pool or free trials. It might be a free trial or a freemium type of model.

The free users involve decision-makers in larger companies that typically might buy a few individual seats. Users will pay out of pocket from small budgets or they will not maximize the potential. You are using that to get to a higher level of authority to build a sales opportunity and do a standard sales process. These are the three things that we are focused on. We have inbound leads and an outbound engine that’s driving demo requests top-down. We have inbound signups that are driving free self-serve deals and the product that sells. We are doing trade shows and driving deals there as well.

We covered both the go-to-market success and the failure story. What can you share from a go-to-market success point of view?

One of the things that come to mind that I can share is around pricing. We realized that we had, in Aligned, only a free and a pro package, and then the enterprise contacted us. We did a big research in the market. We saw that in the entire sales stack industry, there was almost no company that had that initial pricing point for self-service.

We opened $35 on a monthly. We opened that tier, experimented with it, and saw an interesting thing. In the beginning, a lot of people weren’t even buying that. It increased our conversion for the pro, but it created more differentiation. People were safe. They felt safer that there was a smaller one, but they wanted the one with more features. That was a big success.

In terms of failure, it connects a little bit to something that I said earlier. It’s another perspective of it. Our platform helps the entire revenue organization, both sales and CS. There’s even a partnership use cases and some SDR sales development use cases there. We initially looked at and mapped all of these buyer personas and defined them. Think about it. You have AE and VP sales. You have both the end user type of buyer persona and the authority for direct sales. You are looking at AEs, VP sales, CROs, revenue operations, ESMs, and partnership managers. It’s a lot.

We were trying to build it like that initially. It’s very helpful, but then we realized that if we are trying to target all of these in terms of building channels like marketing or sales channels to go to market with, it’s going to be an overkill. In messaging, when you try to better one burdened hand, so you try to get all of them together, you are getting nothing. You are getting messaging that’s too fluffing.

If we're trying to target everyone in terms of building channels, marketing or sales channels, to go-to-market with, it's just going to be an overkill. Click To Tweet

Those were the biggest challenges. It took us a while to figure it out. We are still serving all of them. We are starting in sales. From sales, we are expanding. A lot of times, during the sales process, the sales VP will bring the VP of CS or the CRO will want to buy for sales. That’s the core messaging that we put out there. We do 80/20. We decided to do 80% of sales and 20% of the rest in messaging or effort. The CRO will start up sales. From there, during the sales process, it will expand to others or post-sales, it will expand to others.

This changed everything, both in the simplicity of going to market and in conversion success. Long story short, and it repeats itself, niche down as much as possible and be very accurate with the target market through ICP and then expand over time or find other ways to expand during the sales process or post-sales for expansion.

B2B 53 | Aligned
Aligned: Niche down as much as possible and be very accurate with the target market, your ICP.


We keep coming back to that core insight in the go-to-market, which is the ICP. You need to be clear. You can say, “I’m telling to sales organizations,” but that’s such a huge market in itself. You need to hone it down into who within sales. Is it SDRs or AEs? Is it the sales leaders? Is it the inside sales or the SDR leader? Is it the rev ops? There are so many of the personas.

We didn’t even talk about the different segments. We talked about the verticals. You said you are focusing on tech. There are so many industries. Even within tech, there are so many segments in terms of $0 to $1 million, $1 million to $10 million, and $10 million to $50 million or $100 million. There are so many of these segments as well.

I have seen some companies and it’s not my experience but an opinion, narrowing down a bit too much. For example, they are doing something like a specific industry within sales or one very simple and small problem. The challenge is positioning-wise. You might be very accurate, but when trying to do PLG, you want more volume. You want to go to a bigger audience.

Also, positioning-wise, you are, from the get-go, creating positioning of something too small. There’s somewhere in the middle. That’s what we are trying to go after. We are trying to be something that tells a story, tells the vision, talks about the long-term, can move quickly, and is not trying to build all versions at once.

You also mentioned the complexity involved in managing the PLG, the self-serve, versus the PLS, and then the actual direct sales. From a lead gen perspective pipeline and then close, how has that mix evolved for the last couple of months?

It has all been growing. It’s almost impossible to build everything at once. We didn’t try to do the actual at the beginning. We tried to only do and only build the PLG virality to acquire the leads initially and then move quickly to capturing demand, creating demand, and doing thought leadership. We focused a lot on that at the beginning because we wanted to have a very clear funnel. We have people signing up and buying. It is people signing up and us helping them unlock value. It is then getting from there to authority and then building a product-qualified account.

It's almost impossible to build everything at once. Click To Tweet

From there, there is the sales process. That’s going to be a sales process that’s post-value. It has post-value validation or value realization. You have a team already used it for a while, and then you don’t have a trial through the sales process. We were doing that while we were running referrals a little bit. We had a lot of referrals from VCs and a lot of connections and we were still getting inbound. That was already very hard because it’s a different sales process.

You have the people who started top-down. They have already trying and using your product for a long time. You are going through building business cases at a high level where this helps, doing discovery with the leader, and helping with comparisons, and negotiation. Whereas if you are starting top-down, even not the outbound and putting outbound aside, then suddenly, in the lead process, they were telling us, “I want to go and use the free.”

One of the biggest challenges that we had there was figuring out how to separate the two. It was only the point where we felt that we were executing a different sales process well. With top-down, we are executing in a certain way versus bottom-up. If it’s working and things are closing within a few weeks, then we said, “To unlock growth and drive enough pipeline, let’s also start building an outbound machine.” We were having all of these things together that we constantly worked on and optimized.

It’s a big challenge trying to build.

It’s taking the long road a little bit, but it builds a lot of strength for the company. It’s optimizing all of these small pieces. We are going to market in a lot of different directions.

It’s a big challenge. I was responsible for building a PLG, and a product-assisted sales at a Series B startup last year in 2022. The go-to-market motion that the board and the CEO decided to evolve from earlier was inside sales and closing to inside sales. The decision was made to grow the free trial pipeline and then make it self-serve and a close buy to the free trial. In addition to that, it was to move up to mid-market and then do a sales-led.

It was a mess trying to do all of these in 9 to 12 months. We had a whiplash. It was a challenge to figure out what direction we needed to give to the people on the product side, the marketing side, the content side, and the sales side. Who do we hire from a sales point of view? Is it someone who can do product-assisted sales or someone who can do cold outbound and close, or they bring their book of business and close? It was such a huge challenge. That was a massive failure story in the end. The company had to lay off 80% of the employees because they struggled with all these different go-to-market motions.

How big was the company?

When I joined, it was around 150 employees or so, and then we brought it down to 75. Eventually, they went down to 15 to 20 employees. That challenge is always there.

On one hand, it’s harder to do when you are that big because then, it’s product, marketing, and sales. It is so many things together with a lot of processes already in place, so it is hard. At this stage where we are at, it’s a lot of agility. On the other side, I also wouldn’t recommend going and trying to do what we did unless you have one of the founders that have done sales and built go-to markets in the past.

We had the confidence that we were two founders that have done these things in the past. We had the confidence that we could experiment with this quickly and get to conclusions or do this quickly and bring more strength. It is generally a best practice to try only PLG and then go to PLS. Try maybe only outbound and at some point, later on, add the PLG. If you can be a PLG company, it’s better to be a PLG company from the beginning. That’s always true.

The advice I give to my clients as well as folks who I advise in general is to think about how you build and layer on marketing channels. You need to nail 1 or 2 channels, whether it is LinkedIn, email, or something that’s working well. Maybe it’s SEO or content inbound. Something has to be working well, and then you start experimenting and layering on top. The same thing goes with this. If it’s PLG from day one, that’s fine. Figure it out and go all in into PLG. Fireflies.ai, for example, I had the founder here on the show. They were all into PLG. They have PLG motion. Once you have that going, then you can layer on sales. It’s not to throw things at the wall and see what sticks. Especially for the early stage, you are doomed to fail if you are going that route.

You need to give it time.

This was a great conversation. There are a lot of insights for the audience. Switching gears a bit over here. What are the 1 or 2 go-to-market skills or strengths that people look to you for? Maybe it’s PLG, sales, or fundraising.

It’s a few things. It’s one in the product-led sales that I have been having more people speak with me about. Secondly, it is specifically around the problems that we solve for our product, which is improving sales effectiveness in complex sales motions and how to standardize sales playbooks. We optimize direct complex or direct sales motion. People go upmarket or they go multi-product. They go into a more competitive space. This is where we typically help the most.

You must have had a lot of helping hands, mentors, or resources along the way. I know that you are a member of Pavilion, as an example. You also mentioned early on that you specifically joined the company to get the mentoring experience from a world-class leader. What resources or who are the 1, 2, or 3 people that have played a pivotal role in your career inflection points?

Professionally, there have been a lot of people. It’s hard to pinpoint one sales guru or go-to-market guru. There’s Aaron Ross with Predictable Revenue in the early days, The Challenger Sale, and Never Split the Difference by Chris Voss. There were a lot of these different people. If I can say a few that were the most unique, life-changing, and big dramatic shifts, they are from actual people in the self-improvement space like Tony Robbins and Jim Rohn.

I have been turning personal development into a lifestyle. That’s one of the things that Jim Rohn talks about. Work on yourself more than your job. That’s one of his mantras. That’s a big part of it, following people like that all the time and watching their clips on YouTube. Tony Robbins specifically talks about thinking habits. He talks a lot about thinking. Nothing has any meaning except the meaning you give it, how to control or how you interpret situations, and which labels you are putting on situations.

Work on yourself more than your job. Click To Tweet

Especially as a founder, I had a huge euphoria or huge event and then a few dramatic things going on that take you 180% degrees to the other side. You start telling a story to yourself of, “Everything is going in a bad direction.” You can find how you can flip it and focus on that and how it can turn out for the best. This is one big thing that affected me. The third person is my wife. She is a huge part of my life. She is always listening when I’m down. She knows how to pump me up and just be there.

Family support, for sure, goes a long way. Going to your second point, self-help gurus. As cheesy as they may sound, they play a very critical role. For me, I lean on Tony Robbins and Robin Sharma. There are quite a few. Jay Shetty is the newest one on the block in that relevant space. It goes a long way. Marc Benioff credits Tony Robbins a lot.

For the readers out there, don’t think it’s very cheesy. They play a very important role, all these self-help gurus. It’s more up to you as to what and how you lean and use those resources and coaches. I have a final question for you. If you were to turn back the clock to day one of your go-to-market journey, what advice would you give your younger self?

The answer that I’m going to give applies to a lot of different things in the workplace. It took me time to realize this. I’m very methodological. I like formalized. I like finding the, “This is how it should be done.” What I have learned over time is that any formula that I learned and then swore by, you need to throw it into the trash at some point because there are constant changes.

It is being flexible to unlearn about how go-to-market strategy should look like for a company that does this and that because that changes. I have done public sales and direct sales throughout my entire career. I built a PLG company. People tell me, “Why are you doing PLG? Why are you not doing only direct sales?” It has changed. The world has changed.

I 100% agree with you on that. The ability to question your beliefs when it’s not useful and unlearn and learn new habits is a big secret for personal success. In the early days, I used to focus on being perfect. I was detail-oriented. Being an engineer by tradition in the early days, it was all about that. Especially in the early days, if you are doing early business building, you cannot be detail-oriented, process-oriented, and strive for perfection. That will not work. A great conversation. Thank you for sharing so many of these insights. Good luck to you and the team at Aligned.

Thank you so much. It’s been a pleasure. I enjoyed this conversation.


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B2B 52 | Clin.AI

B2B 52 | Clin.AI


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

Listen to the podcast here


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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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


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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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


Was it a paid pilot or a free pilot?

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

At what point in time did Audrey decide to pay?

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

That was your first customer who cut your check.

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

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

4 or 5.

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

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

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

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

They’re outbound agencies and cold-calling agencies.

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

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

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

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

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


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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Thanks once again and good luck.


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