Hi there, this is Vijay Damojipurapu and you're listening to the B2B Go-To-Market Leaders podcast. The show where I go behind the scenes with top go-to-market practitioners to discuss their mindset and tactics.

Today I have yet another amazing guest. He is based in the San Francisco Bay Area, super connected across both the Indian startup growth and scale ecosystem as well as the US, and not just in startups but in private equity specifically. Let me introduce PV Boccasam, advisor to private equity firms. Welcome to the show, PV.

Thanks Vijay. I'm so happy that you're running a podcast dedicated to robust go-to-market conversations. I know you've interviewed a bunch of my friends and colleagues in my network. I'll keep sending you better names than the one you have today.

I can be very assured about that for sure, but that's not the reason I had you on the podcast, just to make things clear. I start the conversation around this central question with each guest, and the question to you is, how do you view and define go-to-market?

Look, it has a lot of connotations, Vijay. The easiest one I can think about is that people generally think about it in terms of forward sales motions. I think about it in terms of reducing the risk and the anxiety to the buyer.

So my definition of go-to-market is, what are you doing to reduce the risk and the anxiety to the buyer? If I show up to a problem and someone else has already solved it successfully, it is very easy for the customer to choose who they would go with. A big part of go-to-market is framing it as what is the least riskiest and the lowest-friction path for the customer to buy, as opposed to us to sell.

It is a mental shift that go-to-market strategists have to do. It is great that you have this wonderful budget with the perfect marketing, but what is the customer actually buying, and how are you reducing the risk of buying from you? How are you reducing the anxiety post-sale?

I have never heard this angle of go-to-market before. True to your word, in the prep call you were asking what unique insight you could bring, and you definitely landed that insight, PV, in terms of reducing the risk for the buyer. Most of the thought process around go-to-market involves things internally: marketing, sales, the forward sales motion. Then there is the layer of having a view on the market: why is a buyer even interested in looking for an alternative, and why should they switch? But you are highlighting a significant factor in that, which is how to reduce the risk for that buyer, because they can be happy with the status quo.

Status quo is also a risk that you can highlight for them. Let me give you another angle. You and I come with a set of beliefs. Everyone has them. But I was reading a really interesting book around this: beliefs are not truths. If you wear the customer hat, what is the customer already convinced about? If they are already convinced about a particular tool, product, or solution, trying to convince that customer is very hard.

I think what go-to-market motions have to do is understand what the customer's conviction is, and articulate either a different belief system that you are bringing to the table or give them a view of the new reality. The new reality, especially in the age of AI, is this: if AI does not reduce their risk, if it does not improve clarity, if it does not enhance their operational rigor, if it does not purposefully drive some of the jobs to be done, then they should not do AI. Why would you introduce AI that reduces clarity, increases paranoia, creates chaotic disruption, and where no one knows what their job is? Why would you introduce AI?

We can go very deep on AI in the world of go-to-market, but you brought up a very important point earlier, which is conviction. Beliefs and a set of convictions from a buyer perspective. There is another angle, which is the conviction of the go-to-market team, involving product, marketing, sales, support, customer success across the board.

And partners.

Absolutely. That's a huge part of the go-to-market motion. Conviction from a buyer side is one, but more importantly, what is your conviction, your read on the market, your read on the buyer segment or the problem set, and why is what you are bringing to the market different? Are you convinced about it?

Let me introduce two concepts that are unique to how I spend a lot of my time thinking about go-to-market motions. The only way to break a customer conviction that they already believe is to have measurable proof. That might still not convince them. They might still say, look, I have never gotten fired for buying IBM. There is no reason for me to believe that moving from IBM Watson to Cloud Code is going to buy me anything. It does not matter what Cloud Code says or co-work or design or mythos. If we are an IBM shop, we are going to stay one.

So then the question becomes, what can you co-opt as the incentives to change behavior? If you cannot change a customer's mind or their conviction, you have to move to what is a coalition of incentives that you could create for them that would change their belief. Incentives are different than convictions. The intent was to say, look, I do not get fired for buying IBM, and they have deep conviction of that. But if you let them know that there is a new set of incentives, that they now do not get paid for what they know, they get paid for learning about things they do not know, then you have shifted the economic buying opportunity.

If someone says, why are you a huge evangelist of driving AI into private equity? I have written papers around AI operating partner roles. Every operating partner should have an AI to it, because I think it is going to have a dramatic impact on the margins. The way you handle the changes in customer behavior is understanding what incentives are going to change their behavior. Otherwise, they will not change.

That's a good wedge and segue into something bigger picture. If you can walk our listeners through your career journey, how you got started and then what led you to what you're doing today.

Sure. Let me start backwards. Today, like I mentioned, I am an advisor to private equity firms. Right now I have two private equity firms that I work with. One has a very US-centric AI focus. The other has an India-based US-centric focus, which is India-based software and enterprise SaaS companies that want to come to the US. I am very happy to have the privilege to serve on the boards of these portfolio companies owned by these private equity firms.

How did I get there? Largely because I have had the expertise over the last 30 years to build a really good understanding of what it takes to scale private equity owned or public B2B enterprise software companies. My entire focus has always been around B2B enterprise software companies. Within this, it has always been around very complex enterprise workflows. I tend not to focus on lower mid-market high-velocity SMB sales. That is not my DNA. My DNA is high-touch multi-million dollar enterprise sales in categories that do not exist yet.

Working backwards from how I built that expertise: I got involved in a company both operationally and with the financial hat on. I was part of a crossover venture firm with offices on the East Coast and the West Coast. Both have since moved on to different strategies and one shut down. I had a prime seat to bring my operator hat to make investments with an investor lens, and then invest with an operational mindset.

My superpower, if you will, is the ability to be on both sides of the table. Operate with an investor mindset, and invest with the optimism of an operator. There is a balance between risk and growth in that. How did I get that? Because I ended up doing turnarounds of venture startups that we had invested in that peaked out at twenty million dollars. They were profitable, but they had really no place to go. I brought in a turnaround operator's mindset, made calculative bets, and sold those three companies as a turnaround operator to strategics.

How did I get to even that? The VCs I had invested with said, hey, you built and sold three large companies, and you took one public company called Appian public, which will do about eight hundred plus million dollars this year. We do not want you to start another company. Why don't you come help us with the portfolio?

Where did I become an entrepreneur in the first place? Because I was frustrated about how fast things were moving in a small company called Microsoft at the time. Microsoft gave me the confidence, the go-to-market thinking, the product mindset, and the competitive mindset in the very early years. I was there from the early 90s to 1997. When I got my seven-year itch, I decided to start my entrepreneurial journey.

I went from working for one of the greatest companies on earth to leaving it during its lean years. I kid that when I left Microsoft in 1997, it did not do so well for a decade after I left. But then I ended up creating three categories that still exist today. When I started Entevo, there was no category of identity and access management. We created that category called IDAM. When I sold that to Symantec, I moved on to creating yet another category called GRC, which still exists today as a multiple-billion-dollar entity.

What does GRC stand for?

Great question. GRC stands for governance, risk, and compliance, which is now a core part of anything we talk about. Then I moved on to understanding enterprise risk management. I went from identity governance to GRC, to a higher level which is enterprise risk management. Then I took that risk management mindset and moved to private equity, because underlying venture and private equity capital allocation is the notion of understanding how to underwrite risk.

That breaks the full circle of what I do, which is understanding where risk comes from, how to underwrite it, and how to make money from it.

Amazing story. It reminds me of the Steve Jobs quote: do what you love, and you never know how the dots get connected. The way you articulate your journey, it is not like you had a vision of, hey, I want to be in private equity. But each step that you took for the next phase built you for the next phase.

That is right. Stepping away from a cushy general partner job at venture capital to go back and fix a turnaround company, a twenty million dollar, ten-year-old company with culture issues and churn issues and positioning issues, why would I want to do that? Well, if I had never done those three things and gotten my ass kicked, I would never have learned the discipline of what it takes to sell to private equity. Going through a private equity diligence process kicked my ass. I learned what it takes.

When I say to my current CEOs that I am supporting, look, private equity is going to strip you naked anyway. You might as well be buff. Give every part of your business a workout. If your arms are strong and your legs are weak, they will tell you, go do more workouts of your legs. Not everybody can be strong in all areas. It takes a lot of reps in a lot of different areas to get really good at it. But you have to be really clear. Are you a product-driven enterprise? A sales-driven enterprise? Or more of a market-partner driven enterprise? All three have three completely different GTM motions, and all three have three completely different CEO DNAs.

You cannot take a product GTM DNA and put them in a sales GTM DNA. I have had the unique fortune of having screwed up companies in between to learn the other DNA. I was a product-driven GTM guy before, because product came first. Then I realized, no, it is really about understanding buyer personas and thinking about a biodome. So I moved to a sales DNA. And I realized that meant truly scale. The zero-to-twenty game is different than the twenty-to-one-hundred game. If you want to go from one hundred to four hundred, or four hundred to a billion, you have to understand the partner DNA. Because you can only take it so far on your own. You will have to influence sales. How do I get Accenture or TCS or Persistent or any of these companies to build a hundred or two hundred million dollar practice on my product, on my platform? So all three DNAs have three different mindsets, and now I get to help other companies do that.

Each story you shared, we can go deeper into it. Let me surface what will be super helpful for the listeners. How and when did you arrive at what your DNA is, which is you're not cut out for SMBs, you're surely not cut out for consumer, but how did you arrive at the notion that you are made for enterprise sales?

When I was at Microsoft, we had a very unique position to be the largest consumer company in the world. We were selling boxes. You would go to Egghead Software or later download software. You would go pick up a Dell laptop and turn it on and get Windows or Office. But when Microsoft decided to go to the enterprise, this was 30 years ago, I don't know if they knew how to spell enterprise, because they really thought that people in large data centers would stick a CD in across thousands of machines and hit setup.exe. I went out and visited a whole bunch of customers and said, that is not going to happen.

If you think about how the enterprise products inside Microsoft evolved, they literally had no idea of how to go from pushing boxes through distributors and CDWs into classic enterprise mode. In consumer, they learned their lesson too, with trying to sell the Windows phone, which turned out was not the same thing as pushing boxes either.

To answer your question, it helps to have your blinders on. If the jockey on this horse knows only to stay in this lane, you are going to figure out how to run faster, better, smarter, and more efficiently in that lane. The only lane I know is B2B enterprise software. Now, that software lane has evolved from selling enterprise software to selling what I call ghetto SaaS, which is ASPs, hosted people's software like Oracle. To pure SaaS. To SaaS that was sold in an enterprise software world. To SaaS sold as subscription software. To on-prem software sold as subscription software. To what we have now, which is vertical SaaS software that can potentially be sold as services. Purely software-as-a-service evolving from services-as-software, largely driven through forward-deployed engineers. To what I call outcome-based software, where you only pay for the outcomes I am producing.

It goes back to the other point that GTM is around understanding and getting paid for measurable proof. For example, if I were a cybersecurity company selling into a large enterprise, I would only pay the cybersecurity company for every cyber event they resolved. They could charge me $10,000 for resolving the event. But if you are having five trillion events in a global enterprise every day, and only two or three events are material to my business, I will pay you for that. You can charge me $10,000 an event. That is an entirely different shift in go-to-market mindset and even the business model.

If a security vendor is making twenty, thirty, fifty, a hundred million dollars selling their security solutions from the gazillion companies they have bought, I would tell the CIO of the largest software company, at the end of the year I might still pay them a hundred million bucks. But show me ten ten-million-dollar events that were worth solving that you solved for me.

If I have to extract the insight to the question I raised earlier, why enterprise versus SMBs, it is almost like the scale and the complexity involved is what I'm sensing, which is completely different from an SMB self-serve or maybe a small sales motion.

It comes back again to this question of measurable proof, or capture of enterprise value. I am happy to pay you a hundred million dollars in the enterprise. But can you, let's say in cybersecurity, show me ten ten-million-dollar events that were worth solving that you deserve a hundred million for? I would happily do that. If you are GE or Boeing worldwide, I do not know how big the cybersecurity budget is. If I were an enterprise sales guy selling for the aerospace defense industry, I would tell Boeing at the end of the year, on January first, my job is to show you that I prevented a billion dollars in loss for you. How much is that worth? That is worth a hundred million dollars for me.

I will underwrite a hundred million dollars worth of value for you today on December 31st. You better keep the check ready, because I am going to come back with receipts. I can prove to you measurably that I stopped attacks from nation states, sovereign states, that are going after your IP and assets. That is worth billions of dollars. You are paying me one to ten percent of its value, pay me by the end of the year. But you must first demand from me the measurable proof that you captured value. Then I can do all my belts and dashboards and say, okay, I have been able to solve ten-million-dollar events for you. That makes me deserving of your hundred-million-dollar check. And by the way, if you remove me for next year, you will have no idea what risks you are underwriting for the upcoming year.

Especially for enterprise, it's super critical to be clear on how you're so sticky in their existing workflows. To take that out is a lot more expensive. And going back to the point you mentioned earlier, it's all about how do you understand and reduce the risk while delivering the value.

A hundred percent. I am going to add one more layer to it. If your customer cannot retell your value proposition internally and externally, you do not have a GTM motion. Because you have neither allowed them to capture the value, nor deliver the value, nor communicate the value. It is your job as a part of your go-to-market motion to capture the retelling of that value internally and externally. And if you do not help them do it, you have not done your job. You say, I provided value, PV. Okay, show me where it is. Tell me who has communicated it to whom, and has your customer told its internal customers why Vijay's software is valuable?

So spot on. Just two days ago, I conducted a cross-functional workshop with product and sales when they were looking to do a massive displacement for a big competitor. My whole point was, yes, you can build an amazing narrative, but are you enabling your champions in your target accounts to tell that story on your behalf? They may be passionate about your product, but do they have, on an emotional basis, been moved and enabled to tell the story internally on your behalf? That is super critical.

Exactly. When it comes to enterprise GTM motions, especially in the context of the uncertainty and the fog that surrounds us around macro, micro, and geopolitical risks, my view is that the GTM leader's only job is to be the clearest thinker and doer in moments of great uncertainty and risk. If you are not providing clarity to the customer, you are just adding more risk to the customer. The reason people get away with selling complex software, especially in cybersecurity in a world that keeps on giving, is because the target keeps on moving. How come we have multi-billion-dollar security companies and the security threats keep going up?

That is why you have to really think through what this new enterprise stack looks like. I approach it from a capital allocation perspective. If I have one dollar today, would I spend it on product, on compute? On customer marketing, customer education, customer coordination, customer context, customer trust building? Think of it as building customer trust. Or would I spend the dollar on vanity marketing and vanity metrics, which includes hiring a whole bunch of people? To simplify it: am I going to spend that dollar on compute (code), or on reducing risk for my customer, or on throwing bodies at the problem (labor)?

It's quite clear where the GTM for AI-native companies is heading, because the growth we've seen for AI-native companies is five times traditional non-native SaaS companies. The question is why. Because the cost of building has come down drastically, which means they need to focus more on building traction. They need to clearly understand the buyers, the go-to-market, and the distribution.

Exactly. The product building is becoming a commodity with AI. If you think about my view on what the enterprise stack looks like, an enterprise is a system of systems. At the lowest, foundational layer is a system of trust. At the topmost layer is your system of engagement, a system of interaction. Everything below that is what people are jockeying for. Am I a system of record? A system of intelligence? A system of orchestration? A system of journey? A system of context? Whatever. But before you layer the compute stack on, there is a system of trust.

The question is, for that given dollar, are you going to first create the system of trust with your customers so they can believe you? Or are you simply going to buy more compute and more code? Or simply add more people so you can sell more bodies and systems to solve the problem? How you allocate capital in this new enterprise stack across computational elements, context-specific workflow-specific enterprise issues, coordination between silos (AR, AP, invoice, goods receipts, supply chain), or the foundational trust, defines your GTM.

To make this more actionable for the listeners, how are you applying this framework to the portfolio companies you're advising, or how did you apply it in the three exit scenarios you had?

It is a philosophy and a framework for go-to-market. It is how you view the enterprise, both as a buyer and as a seller. Enterprises today do not wake up every day and say, I want to buy a platform. Because if every vendor is selling a platform, how many platforms are they going to have? It is like saying every element in your kitchen is a plate or a bowl. What are you going to do with a hundred bowls? You need a combination of multiple things.

So if you consider an enterprise itself as a platform, because they are running the business today, it may have legacy systems or what we call foundational systems, but that is a core system they are running today. That is a core platform. You cannot come around and say, here is another platform. My first counsel to listeners is: do not try to sell a big P platform. Unless you are a ServiceNow or a Salesforce, do not even try to sell a small P platform. Because even Salesforce is a small P platform; even ServiceNow is a small P platform, because they still have to connect to all the other systems the customer has: claim processing, payroll, and a whole bunch of other stuff.

The bigger issue is going back to the old jobs-to-be-done concept: what system are you eliminating or automating? Systems of record are not going to go away. Systems of measurement and observability are not going to go away. Systems of intelligence, insights, and dashboard applications are not going to go away. They are all going to be submerged into the question: on what customer journey will the system be applied?

So most AI-native SaaS applications are going to be systems of orchestration of either a system of record interacting with a system of intelligence, or a system of customer journeys, that is based on a layer of trusted LLMs where you know they are not hallucinating. They have actual enterprise data with enterprise LLMs built into them. With a compelling system of engagement on top. And the system of engagement does not necessarily have to be chat. It could be a video walkthrough of how to audit a shop floor filled with robots. It is no longer a set of documents you threw at me saying here is a bunch of compliance documents. It is a physical video walkthrough that you take your phone through to walk through the compliance and safety practices on a shop floor that has humans and robots working together.

So when you bring this framework and the lens to some of the companies you're advising, or maybe you applied it as a turnaround CEO, how did you translate that into go-to-market execution? How did execution have to change?

You have to put yourself in the minds of the buyer, not the seller. What does the customer buy, not what we are selling. If the customer is buying a system of journeys for claims processing, the output they are looking for, the measure of proof, is: the cost of processing an insurance claim was thirty-eight dollars. Can I make it thirty-eight cents?

What system should be in place that captures the thirty-eight-dollar cost they are doing without us, and the thirty-eight-cent cost they are doing with us? You could show the systems in place that say, here is where you are capturing value, and here is why the cost of approval or denial of a particular claim went from thirty-eight dollars to thirty-eight cents. So I am selling them a particular system, not a platform. Which means the professional services, implementation, partners, and so on all go away. What you are telling the customer is, if I show you the reduction in time, cost, and value from thirty-eight dollars to thirty-eight cents, and you are doing more throughput per claim officer every week than before you put our system in, here is the receipt, here is the proof.

Measurable proof is a consequence of putting systems in place. You start with the thirty-eight cents in mind, by helping articulate the belief. Coming back to what we were talking about: if the customer is convinced that thirty-eight dollars is cheap enough, the only way to solve the problem is to show that it can be done for thirty-eight cents. If you show them it can be done for thirty-eight cents with measurable proof, they will ask, how the hell did you do it? What do I have to do to change it? They will say, I am going to change this system, this system, this system. And if it means changing how they are onboarding insurance brokers, or how claims officers are spending their time reviewing documents, or where bad documents are being submitted, you should be able to catch that in the first five minutes of the claims processing process, not waiting until the last ten minutes.

This is a great piece of advice for all the SaaS companies who have to compete with the AI-native companies eating away their lunch. The lens they need to bring now.

What I am saying is, help reduce the decision fatigue of the customer. Do not make it hard for the customer to think about why they should go with you. Reduce the uncertainty and the risk for the buyer. By doing that alone, Vijay, you become a trusted partner, because you are telling the customer, I am reducing the risk for you. You understand that by going with us, it is less Buddhism for you. It is a less risky decision than staying with what you have today versus going with me. But that can only come through measurable proof.

We are coming towards the end of the show, last couple of minutes, which translate to my last two questions. One is, you're super active in the private equity world, both as an investor and operator. You have the eyes and ears of CXO-level: CEO, CRO, CMOs. What is the one topic that is super critical for the next six to twelve months for private equity-owned companies from a go-to-market angle?

For private equity-owned operators and CEOs, listening to their customers on how AI can be embedded into their enterprise workflows is not just a product and GTM selling question. It is about adoption and diffusion into the enterprise. Most technological advances have come from one and only one thing: adoption takes time, and where the time goes is in organizational redesign.

People talk about change management. What they really mean is that it is not enough to enable everyone with Anthropic Claude Code, or Cowork, or design, or methods. It is what happens after you give them all that. What is the impact to the organization, and how does the organizational design change? Do you want to absorb it? Roles are going to change. Tasks to be automated have completely changed. There are hours and hours of automation that were done that suddenly freed up thirty hours of a business analyst's time. How are you going to redeploy those thirty hours into productive use, instead of saying you just got laid off?

Private equity has to have a mindset that it is not just about cutting costs and improving margins. It is how do you organizationally redesign your 3,000-person company to behave like a 10,000-person company that is producing ten times more margins, ten times more growth, the same amount of capital allocation, without leverage.

I think we should do a follow-up podcast later this year on AI challenges and deployment for private equity-owned companies. That's entirely a huge topic in itself. Last question before I let you go, I know you have a flight to catch: if you were to turn back the clock to day one of your career journey, what advice would you give to your younger self?

It is never a sprint. It is always a marathon. Pace yourself. Finding the tempo and the pace at which you operate is going to be very critical. I wish someone had given me that advice: pace yourself, young man. It is a long way to go. It is very easy to burn out. Especially when you join companies like Google or Microsoft, there is a tendency to behave like the world is going to come to an end soon. What you realize is that whether it was the steam engine, electricity, or the mobile phone, it takes time for adoption. It takes a long time to be able to see your impact. So measure daily, but look for long-term impact, not short-term shocks.

Especially in this world of high-dopamine TikTok consuming, people need to rewire their mindset. Life is a marathon, not a sprint. It is important to conserve our energy for things that matter the most.

Excellent. Wonderful conversation, PV. Good luck to you and the team and the folks you're advising. Look forward to having you on round two later this year.

Thanks Vijay. Look forward to seeing you soon, and keep doing the great work for the GTM community.

Hi there. Thank you for listening to this episode of the B2B Go-To-Market Leaders podcast. I have all of the show notes and a full transcript on Stratyve.com. Subscribe on Apple Podcasts or wherever you get your podcasts, and leave a rating and a review. Your comments will help other go-to-market professionals find this podcast.