B2B 51 | Go-To-Market Engine

B2B 51 | Go-To-Market Engine


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

Listen to the podcast here


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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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


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

Coming back to Nitro and People.ai.

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

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

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

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

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


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

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

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

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

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


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

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


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B2B 50 | Factors.ai

B2B 50 | Factors.ai


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

Listen to the podcast here


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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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


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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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


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

We don’t put our own product.

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

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

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

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

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

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

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


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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Thanks a lot.


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B2B 49 | Carabiner Group

B2B 49 | Carabiner Group


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

Listen to the podcast here


Leading The Carabiner Group With Cliff Simon

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

Thank you for having me. I appreciate it.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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


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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

“All you do is just talk.”

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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


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

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

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

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

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

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

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


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

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

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

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

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

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

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

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

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

Where can people find and learn more about you Cliff?

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

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

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


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