E21: From Building Startups to Betting on Them with Jason Gelman of Primary Ventures

I'm excited to be joined today by Jason Gelman, who is an operating partner at Primary Ventures and co-founder of Jump, which is a revenue calendar for revenue leaders, which we'll learn a little bit about. Primary is an early-stage venture capital fund, so primarily seed and pre-seed, that takes a strategy of low volumes of investments, very high conviction strategy, and then backs that portfolio with a ton of resources like Jason. And they've companies like Alloy Alma, Chief Electric, K Health, Vestwell, and many, many more. And prior to Primary, Jason spent 4.5 years at Compass, where he was the head of revenue strategy and operations from somewhere around $100 million—memories are hazy—all the way through to a $6 billion revenue run rate and a successful IPO, which raised $450 million in capital at the time. So lots to get into, and appreciate you joining me, Jason. Thanks for having me.

And this is my very first podcast, so I'm really excited about it.

Good stuff. Hello and welcome to the Revenue Leadership Podcast by Topline. I'm your host, Kyle Norton, CRO at Owner.com. And every Wednesday we dive deep into the strategies and tactics being used to drive success by the best revenue leaders in the world. So join me as I sit down with revenue operators to discuss actionable frameworks that you can implement in your business today with no fluff, no sales pitches, and no platitudes.

This episode of the Revenue Leadership Podcast is brought to you by Superhuman. Superhuman is an AI-powered email app that helps sellers respond, collaborate, and close faster with features like inbox triage, with storage, automatic reminders, and collaborative email drafts, reps can filter out distractions to focus on what they do best: selling. Get the email experience that keeps deals moving. Try Superhuman free for 1 month at superhuman.com/pavilion. So what did I miss in the intro?

Give people like your 60-second background, anything that I failed to cover there.

Yeah, sure. So I actually started my career as a lawyer. Very quickly realized that that wasn't the thing for me and got an opportunity to jump into the tech industry and have been there ever since in the New York tech scene. I had this idea that I was going to be a business builder. I didn't quite know what that meant, but I love the energy and the innovation in the tech world, and that ended up manifesting itself in BizOps and then kind of RevOps. And that's where I Really got my experience over about 13 years at 4 different companies, 2 martech SaaS companies prior to Compass, and then Compass was really tech-enabled. And the idea was let's bring the best of the go-to-market SaaS playbook to building a modern real estate brokerage. And then for the last 2.5 years, I've been at Primary. This is the first time working at a VC firm versus building an actual startup.

Very cool. So first question that People might be wondering, what the heck is an operating partner? Yeah, good place to start.

So, uh, an operating partner is, uh, somebody that works at a VC firm that does not write checks into startups or serve on boards usually. Uh, but what they do is once the check is written, they bring some kind of, uh, functional expertise and domain expertise to working with the startup as a consultant, advisor, support system for those startups. And the role really varies based on the stage that the VC firm invests in. So I work at Primary. We are seed investors. Every time we invest in an amazing founder, amazing company, amazing vision, what are we also investing in? Pre-product market fit, sales, early scrappy hustle. And so that's my version of being an operating partner. You can imagine if you're a Series C or D VC firm, your operating partner there is probably not rolling up their sleeves and doing creative things around how do we get our first customers. It's much more the scaling the machine and board level and strategy level topics.

Makes a ton of sense. We could do an entire episode on founder-led sales. I think that's the most common LinkedIn message I get coming inbound is I got 3 or 4 customers What do I do? How do I scale this thing? It's, it's, it is a really difficult chasm to cross. And so it's great to see that you guys are supporting founders there. It's badly needed. Yep. And so is operating partner in your previous title, VP go-to-market, is that largely the same, just sort of a different seniority now?

Yeah, that's right. Okay, cool. You know, VC firms typically, and one of the things you have to learn if you ever do join a VC firm is it's an investment firm. It's not a startup. And so some of the cultural things and the things about operating rhythms, titles, org design, it's just different than a startup. And partner at most firms has some maybe equivalency to like an accounting firm or a law firm where there's like a partner team. And so that's really the only material difference is like I've joined the partner team. Cool.

And so you'll work across every portfolio company with Primary?

In some way, yes, but we have at least 100 companies in our portfolio. I don't work with all of those. Certainly some of them are scaling or growth stage companies where I might be able to help and create less leverage. But let's say there's a pool of 50 companies that I might be actively in touch with at a given time. I could not possibly do deep work for 50 companies at once. And so the The way that we try to do it is, uh, first, there are certain companies that clearly need the most help or are asking for the most help. That's one way we can sort of prioritize. Another one is companies that we just invested in. And so we're A, building a relationship, building up our relationship and working together. And B, that's a really important time for us to learn the business, learn the customer. So that's an example of how we could prioritize. And there's a few other ways as well. And so in reality, what I'm doing is probably working very, very closely with 6 to 10 companies at once. Keep— and then I'm in touch and in rhythm with another 10 to 15 companies, like whether it's a one-to-one or check-ins or, you know, trading notes or doing some work there. And then I also do bring in outside consultants at some points where there are direct matter gaps, gaps with domain expertise gaps that I can't build. So like we do have other people that come in to help where I just don't have the right relevant experience. Nice. Okay, cool.

And so what's Jump? I read revenue calendar. I had— I didn't know what that was, but it sounds interesting.

Yeah. So Jump is a new startup that I'm a co-founder of with two other friends and partners of mine. What we're doing is building a tool that's built for revenue leaders. So they are the user that we have in mind. And it's really to solve a problem that myself and my co-founder Jordan Kennedy have experienced ourselves over many years of running revenue organizations. And the short explanation is that we think that the calendar for a sales-led organization has a lot of important data and insights, but it's stuck in the calendar. And we have always had issues getting data out of the calendar to drive insights and impact. And so that is the thesis for the company we're building. And we're actually doing it in a different way than the traditional VC-backed startup. And I'm happy to explain more about that if helpful. Yeah, let's hear it. Yeah. So one of the reasons I joined Primary was that I felt like there was a lot of innovation happening in the world. And when you're operating heads down at one startup, it's very easy to like all the innovations happening and you're just kind of focused and grinding. And we're going to build the best tech-enabled real estate brokerage in the world. And it's like, well, hold on, what's happening in the rest of the world? And so part of joining Primary was to really see a broader sense of innovation. It was also though, for me, I had always had the ambition to start my own company and I felt like I needed a little bit of a creative spark again. And so Primary, it's like I get to work with all these amazing founders doing these really ambitious things. And when I got there and started to work with all these different founders, I got inspired. Like I said, if I'm coaching and teaching founders how to do this and bring a product into the market, I got to be able to do this myself. And so that was point one. Point two though, is that when you work at a VC firm, it really gives you sharp insight into which businesses should raise venture capital and which ones shouldn't. And a lot of interesting software products that come in that solve problems for customers, but that probably should not raise venture capital. And venture capital, you know, you get on the VC treadmill, you are really shooting for very, very large outcomes. And so VC is a great tool for certain kinds of businesses that have the market, the potential, the ambition, ambition, innovation to like become an enduring iconic company. But then you see a lot of businesses and it's hard to figure out how they're going to— is that the best expression of the business? And so when we came up with our idea for Jump, partly informed by my experience at Primary, I said, I think this idea can help customers, but I don't think it is a worthy business for venture capital.

Let's go one layer deeper there. So you get a bunch of these companies coming across your desk. How do you like to explain who should raise venture versus who should bootstrap or go a different funding route?

Yeah, I don't know that there's like a perfect one-size-fits-all answer here, but we're living in the age of sort of like AI innovation and transformation and what used to require lots and lots of capital to get a company or an idea off the ground doesn't require as much right now. And so there's a lot of examples of companies that maybe 3 or 4 years ago would raise venture that should really, could really be started as a test and you can build a product, get it to market and validate the idea and keep optionality open. And so one answer to this is a company that comes in, has almost no product built or a little bit of product and has no real customer proof points may not be a great candidate for venture capital in today's day and age, especially in a crowded market, like something like go-to-market SaaS, where there's a lot of incumbents, there's a lot of new entrants and the lines are getting blurred across all these different categories. And so each new company that comes in to raise a seed round, the bar is just really, really, really high. For a seed investor to say, like, how does this one company become the next Gong or the next, you know, category-defining business? So that's one, which is like, go show that you have amazing revenue traction and usage traction early and then raise venture capital because you've clearly like broken through. The other one is, I think that people misunderstand, like, I probably understood this a little bit before I joined Primary, but now I really deeply understand it, which is I think you raise from institutional investors, even early stage, you are in the VC game. Like, meaning you can raise a seed round, but oh, it's early and, you know, and we're, but every, we only do as a firm 12 to 15 deals a year and we see 1,000 or more. And so those 12 to 15, part of our underwriting and our process for research and diligence is like we're betting on a founder, a product, and a market that has ambitions to go big. And some founders may come in and not realize that you raise a seed round, oh, but I'll figure out what my growth ambitions are later. And you have to be really aligned with your investor on exactly what you're going for.

Yeah, makes a ton of sense. And so Jump is trying to pull out information. So you'll provide the calendar for a sales team to use that's better integrated into a CRM or a data, data layer or something like that. Yeah.

So Jump, what Jump is doing, we're going to— so our thesis is like unlock the calendar. There's a lot of important things in the calendar and we're going to build 3 different products around that. But the one that's live today that we're working with our very first customers on is called the Revenue Calendar. And what it's doing is going into the calendars of all the different people that speak with customers in your organization, SDR, sales, CS, AM, and leadership. It is finding all the external meetings. It's unifying them onto one calendar so that if you're a revenue leader, you're a CEO that's commercial leaning, or you're any other VP or C-level that has to be in the flow of like, what, which customers are we meeting with? It gives you one place to see all this information. And the idea for us and the reason we built this was almost to solve like a problem that we had. Was by the time you get to the call recording, it's too late. Like the goal of revenue leaders is that they provide the most leverage. And, you know, by the time the call recording, the meeting happens, the call recording happens, great. You can coach and teach on what to do next. But there's a lot of stuff that you can do if you know where to proactively intervene and your revenue leader, you know, like yourself, your CEO, every Monday morning you show up, your calendar is booked solid. You're already in tons of meetings every week. You have to sort of chase people around if you want to know what the flow of the week. And so for us, it's like, this gives you a chance to optimize your time as a leader, your leverage, and be where you want to be, whether that is helping internally prep for things or check on things and mitigate risks, or it's external, like I want to join 3 customer calls a week and like, which are the right ones for me to join?

Very cool. Um, okay, let's get into our, our two main topics. So topic one is you making this operator to VC transition. A lot more and more folks are doing that, so I'd love to understand why and how and lessons there. And then we want to dive into what you've learned now on the investment side that you wish you would have known as an operator, because I think viewing the same problems from new angles is, is such an interesting way to, to acquire new mental models and really learn. So we'll unpack that for all the operators. So let's start with the transition to VC. So a recent post of yours, you mentioned why people advised you against going into it, and obviously you did it anyways. What, what did— what made you want to go into venture in the first place?

Yeah, so I can't tell you that this was intentional, like I had a specific plan to do this. The opportunity did fall into my lap through a friend of mine that had been consulting for Primary and they were going to open this role. They sort of talked to her about the role. She couldn't do it. They said, who do you know that has an identical skill set to you? And she introduced them to me. So that's how it happened. Um, when I was leaving Compass, I did have some idea I was doing some soul searching that I had done similar roles and I'd sort of climbed the ladder in revenue strategy and operations for 12 or 13 years. And I was ready for something new. We had just gone through COVID, a very intense IPO process. I had just started a family. I just like my priorities were changing a little bit. And so I didn't know what new or different meant. And then this opportunity sort of materialized. And so I started to research it and develop my own thesis about it. And I talked to Primary, got excited, talked to some mentors and they said, don't do it. And then I talked to Primary again and got excited. And then I talked to some more mentors and they said, don't do it. And the don't do it was like, you're an advisor, not an operator anymore. Like you're hanging up your guns kind of thing. And so that was one. Two is like, you don't really have any impact. You're kind of like a little bit of a talking head and you're like a frameworks guy. 3 was like, you're getting more senior in your career and like you're just at this point where like you're well networked and you could be on the next big rocket ship. And so like if you miss that opportunity, there's a huge opportunity cost to that. And there was a bunch of other things. And so like that's what I was hearing. And then I started to say like, okay, well let's make the most optimistic case for trying this. Like what would be the reasons to do it? And I started to just cycle through these ideas over and over again. So it was like one was information asymmetry. I felt like in my career as a job candidate, as someone who isn't particularly well networked or has a huge brand or audience in the world, I go apply for jobs and I have zero information, like access to inside information. And every time you do one of these runs, you do 3, 4, 5 years and it's like, how do you know you're picking the right company? And so I said, number one is if I go to a VC firm, I'm going to have a lot of information asymmetry. The second thing is I don't have a big investor network and my north star at the time was, I think I want to be a COO president of a company. Like that's like the next big thing for me. And I said, if a great growth stage company was to open a COO type of role, to run the business with a CEO who's technical and I was in the room, why would I not get that job? Well, I have a lot of operational expertise. I've done different business models. I've scaled up different programs. I've done more than just like the RevOps, like tooling. I've done a whole bunch of things and that's great, but I've never fundraised. I've never been in the boardroom except the exec team for the board meeting. And then I wait for all the the dump of new projects I have to do after the board meeting, but I've never been in there. And so I felt like the investor side and the board meeting side was a big gap for me that I wanted to fill. I also felt on the picking side, like watching an investment firm analyze markets, trends, like across industries, across business models, across customer personas was a level of access that I just had never I've never had before. And then the other one was I get to be a trusted advisor to 50 of the best early-stage CEOs, and I get to try before I buy, and they get to try before they buy. If I find a mutual fit where I love the business and they love me, that's a— they could pull me into their business that way. And then the last factor was I said, hey, I'm at a seed-stage VC firm. My instinct there was I was either going to come into Primary and eventually join one of our portfolio companies as a COO, or maybe I would get backed by Primary and spin out a company and I'd be the founder and CEO and they would fund me. And I said, okay, so that's the positive side. That's what this could unlock for me. And the distinction that I really felt strongly about was everyone that told me not to do it, it was like an impact thing. It's like, you're not going to have impact in this role. And everything that I was excited about was a learning thing. Wow, this is, wow, I'm going to meet new people, I'm going to be in board meetings. And so I basically chose learning over those concerns about direct impact and owning a specific outcome. And I can talk about the experience, but I'm very happy.

I can tell you, as someone who deals with a lot of early-stage startups and therefore interacts with a lot of advisors and operating partners, there is a big opportunity for impact. Because I don't know how many times I hear a founder tell me something that somebody else told them. It's like, oh, you should think about doing this, you should spin up this. And my instinct is like, that's a horrible idea. Like, what's going on? And, and I— conversely, the right piece of information for an insight, the right framework for an early-stage company can be really inflection-changing. And I've been lucky enough to sometimes get to share that nugget. I get to see a founder who hears something from somebody else and, and that transforms the way that a company operates. I would definitely disagree with the assumption that you can't have a lot of direct impact. I get where it comes from. Like, it's easy to think that from the outside, but yeah. Yeah.

And a couple of things to know about this, if for anyone that would consider this role in the future, your experience driving impact matters. It matters a lot which VC firm you choose. Yeah. Some VC firms, like I know other operating partners and the priorities for them, if they had to stack rank them, are diligence on new deals, LP reporting and presentations, and then the third or fourth or fifth place thing is working with portfolio. Yeah. And so if that's the firm you sign up with, you will not feel like you're actually moving the needle for any of your portfolio companies. When I was working through the decision process, I made myself a promise and I said, I will never ever be the frameworks and storytelling and big idea guy. Like if I do this and I don't feel like I'm solving problems and I'm just saying generic frameworks and inapplicable stories and things that aren't actionable, I was like, I just can't be that person. I'll never do this job if that's the case. And so when I got here, a big part of what I had to explore in my first year was like, where can I actually make an impact? And what is the firm doing today where it's either not making an impact or the opportunity cost isn't right and there's another area I should really try to drive leverage in. And that is an ongoing process 2.5 years into the job, continuing to find the points where there's outsized impact we can make for different types of companies.

Yeah, that makes sense. I actually think frameworks is one of the useful things if it's an actionable framework. And I'll share with a founder— founders are always trying to hire. One of the things I get roped into is how do I get my first VP of sales? How do I figure it out? And I'll give them my framework of how I think about hiring that VP of sales and the questions and the case. I'll give them my case study that I've written, and that's more valuable than any generic advice because they actually have a guide to follow. Totally. So cool. Um, we're— I'm going to come back to this question of what makes a good operating partner versus not, um, but I want to stay on some of this journey. Uh, so what, what made you realize that this was the right choice? Like, how did you realize that Primary was the right fit and, and this is where you wanted to take your career? I mean, we've covered why, why take this, uh, leap. It's all about learning, which I think is awesome, but What made you think the timing was right today?

Yeah. So in terms of the timing, I moved to my house. So I left New York City in COVID, like a lot of other people scrambled to the suburbs. I moved to my house on March 22nd. Compass IPO'd on April 1st. I had my second kid on April 22nd. So in one month—

Of 2020?

Of 2021. Okay. Yeah. All in that 30 days. And so I had hit a point of general craziness and burnout that I needed something to change. And the version of me that would've met startup founders and been like, I'm all in on your vision and let's go build this thing and do that again.

80 hours a week.

Sign me up. And I went out and met all these founders who I'm very inspired by, but I walked away from those meetings just saying, this isn't for me. I just don't have the energy for doing that right now. And at the same time, I felt like I had hit a glass ceiling in my career as like the, you know, the RevOps leader guy. And for me, it's like, no, I want to be the CEO or the COO of a company. Like, that's, that's my goal. And so part of like the right time and the right place to do this was I felt like Primary could elevate my career and unlock a lot more than like just joining the next Series A startup and doing that over again. Makes sense.

And how did you know you were ready to do that? Like, it's tough to know if you have enough operating experience to be able to have the pattern recognition and really be super helpful. What gave you the confidence that you're ready to take it on?

I think so. First of all, like, I didn't have a network in the VC world, really. I didn't have like a lot of people to bounce this off of that had done this job before. So I was a little bit guessing, but I did a lot of backchanneling on Primary and they did a lot of backchanneling on me. And it turns out the New York tech scene ends up being really small and we backchanneled the exact same people at the same time. And they're like, I'm kind of texting both of you about each other right now. And what I heard about Primary was it is in their DNA that they take the management fees that a lot of other VC firms put in their pockets and they invest it in this really robust operating team. And this will never go away. This doesn't, this isn't like a strategy today, gone tomorrow thing. Yeah. We're DNA. And so that was one. Two was I had looked in their portfolio and a bunch of the companies that I knew that they had just invested in, which I would be working with, I felt like, oh, that kind of rhymes with something I did before, or this kind of reminds me of this other thing. And like, oh man, I hope they don't make the same mistakes that I made 5 years ago. And I had a little bit of that. And then they brought me as part of the pre-offer process to meet a few of the CEOs in the portfolio to mutually kind of feel it out. And I love those jam sessions. I thought they were amazing and they had good enough feedback about me that Primary was like, let's do this. So there was a bunch of other signals like that. And I just got very, very excited about all the learning and growth that I would get inside of a VC firm like this.

Nice. Awesome. Do you think you want to be an investing partner at some point? Good question.

I think when I started, I felt like I was opening new doors. So door number 1 could be join a portfolio company as COO one day. Door number 2 is like found my own startup through Primary and get backed by them. They have an incubation program, which I can talk about. Door number 3 was, well, what if I want to be an investor? And so in the beginning, it was very much an open question. I think for me personally, the answer is no. I think our investors are unbelievably talented, unbelievably bright, and I have so much respect for them, but I have so much identity as a builder and a problem solver, and I just like the idea of bringing products to customers and just really deeply woven in my DNA. And what's nice is I get to work with founders to do that, and I have my own startup to do that. And so all the things that I teach and coach the startup founders on, I'm doing myself. It's like, hey, I'm trying to get the first 5 customers and let me explain what I'm trying and then see if we can apply some learnings to your business. So that motivates me a lot more. The investing thing, I do think I would angel invest and do that, but not as like an investment partner at a VC firm, at least for the next, you know, 10 years or so.

Yeah, makes a ton of sense. Um, so you said, uh, I can't remember if it's LinkedIn or somewhere else, but you wouldn't have been good at VC 3 to 5 years ago. So there's obviously, you know, an amount of experience, a, a set of skills that are required to do this well. And, and I sort of break it into these two things. Like, you need discernible skills to know how to build a growth model, help architect a comp plan, understand, like, do market analysis. And those are very tangible skills. But then there's some, like, pattern recognition that you need to be able to develop by seeing a bunch of companies and just going through it yourself a bunch of times to actually be good at this job. This is my, my view, having never done it, obviously. And so is that the right framework? Is it, is it those two buckets of things? And, and if so, um, How do you think about when you have enough reps to have the pattern recognition? How do you know when you've got the skills to go take the plunge?

Yeah, it's a hard thing to explain, but it's like a feeling I had. Like when I got here and I was in my first year, I said, wow, I would not have been good at this job 3 or 5 years ago. I actually think the biggest reason for this is my, let's call it age group or class or contemporaries are now VPs, heads of C-levels, founders. And 5 years ago, maybe they were the directors and up-and-comers and future leaders, but now they're like leaders. And so one really important thing that would not be immediately obvious until you start doing this role, is every single day one of the startups in our portfolio says to me, I need help solving X and whatever X is. One part of my job is almost like an account manager. Like I have to go out into the world and leverage my network of really trusted people or the people that they trust the most to bring them in to solve specific problems that are either in the go-to-market world or adjacent to it. And to be able to backchannel candidates with my contemporary network, to be able to get functional expertise through my network. These last 3 to 5 years, there's a huge wave of people that I've grown up in the industry with that are leading companies right now. And I think that's actually the biggest reason is my network reach and my closest friends that I've grown up with are now in these leadership positions or whatever. And so that to me is the biggest one. The second is also what you said about around business acumen, having a strategy mind, like really being able to break down strategy and map it to execution. Every new cycle you get doing that really helps. And part of the heart, part of the job is how do you go into a parachute into a new company where the founder and team are thinking about this problem space 5 full days a week, and you are thinking about it very, very little and quickly get to a point of decent credibility that you can help solve problems without asking for a lot of training and all that stuff. And so learning how to be a really good consultant is a hard part of this job. It's not anything I've had to do before. And so extra reps building different kinds of businesses or working on different kinds of problem solving at Compass, for example, I did a lot of things at Compass. Under the umbrella of revenue strategy operations. And each one of those things has been somehow applicable to my work here.

This is literally one of the questions I had written down. Like, one of my challenges doing advisory and working with the portfolio companies at GTM Fund and Stage 2 is you have such a lack of context. And at some point in my career, I realized, like, hey, there's no such thing as a best practice. There's, there's high probability practices, there's things that like tend to work a lot, but depends on the customer type, the market context, the stage of growth you're at. And so I actually became— this is classic Dunning-Kruger, but like I became much less certain of the advice that I wanted to give as I started to understand sort of the nuance and complexity of it all. And so how do you find the balance between having proven frameworks that you are confident in and you've applied in your real world versus finding the right nuance in the business? And how do you give great advice given these two things are at tension?

Yeah, this is the hard part of the job. So, okay, is the thing that I've tried to do is each new company I work with, It's like, what is the quickest possible win that doesn't require the deepest amount of fluency in their business that I could find and just solve one problem for them? And if I can do that, there's enough signal and early trust that they'll invest time in me teaching me more about the nuances of their business and their customers and all these things. And so that's number one for me is like, what is the quickest, smallest win that I can compartmentalize and deliver?

First, second, how often is that go smaller with your ICP?

That, that is sometimes it's not usually go smaller with your ICP because a lot of times they want to set up ICP experimentation like they know they don't have ICP and so like, okay, you're, yeah, you're even earlier stage.

Okay.

Yeah, it's like this is really early. It's like I have no customers and no one wants to meet with me. Like, what do I do? And so we have to set up experiments. And so I think one framing I would give is I try to be a little less on the advice side and a little more on the, how do we design the action plan that we want? And then let's go run a bunch of tests and go out in the world and experience it together and make decisions based off that. So that's one piece. The second piece is there are a lot of I would call basic foundations of go-to-market that a lot of these founders need help setting up, whether it's how to run a sales meeting or how to structure their discovery questions to some basic tooling, basic pricing and packaging to take to the market for the first time, basic assets. And the more you work with different companies, the more you hear the same requests across a lot of them. And then you're like, okay, hold on. Now I can invest in building some assets or templates for people because I'm getting the same question over and over. And so that's another thing we try to listen for is like, where is the repeat demand for the same things?

Yeah, makes a ton of sense.

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You had a long run as an operator, and a very, very successful one, especially with, with Compass. And now you're seeing both sides, and I'm sure discovering a bunch of stuff, you're like, man, I wish I had known that a couple years ago. What are the couple— what are the top few things in this first few years as an operating partner that you really wish you had known in your strategy and ops world?

I think from each startup I worked at, there was some, like, lesson that has come back around working at a VC firm that, like, clicks after all these years. So for example, one company I worked at had an unbelievable team, the best collection of talent that I've ever worked with in my life, but really had a product-market fit problem. And we were able to, as a growth organization, and I take very little credit for this, we had some tremendously talented people and leaders there. We were able to get this company to over $50 million ARR without perfect product market fit. And so anyone who's seen scale up before you're ready story is a really painful one. And then you see it from the VC side. We have companies at seed, A, B, C, D, and you see all these different companies and some of them are like ready to have the great unit economics, great foundation, great everything, and they're ready to grow in a really thoughtful way. And so you just see your past come back because you have exposure to all these different companies. And so product, like really hammering home product market fit and understanding what delivering value to customers really looks and feels like is a big one.

And I was laughing because I went through the exact same thing. Super talented team, but we were brute in growth. Every deal had to be perfectly executed, but we just never had product market fit. We never had customers that were willing to do customer reference calls for us, but we still jammed that business to $25 million ARR. And yeah, I learned that same exact lesson very much.

So just because you have the capital, being really honest with yourselves and finding the investors around your table who are really honest about where the business is and what the right next steps are, I think is helpful. The other—

Can I ask one more question about that? So how do you identify that with a founder? What should founders or revenue leaders be asking themselves to understand if they have enough product market fit to go into go-to-market fit mode?

Yeah, I think the biggest thing is some form of sticky usage and then retention where it shows up in the dollars. I think most revenue leaders know the state of their customer base and the product quality and where they are as far as the market dynamics. I think the mismatch typically is like the VCs want us to grow this way and we're only ready to grow that way. And so let's hire too many salespeople or let's raise too much money. And that mismatch is the really hard one. Inside of a VC firm, you just see every flavor possible of different kind of company. And I think the VC world, the world of VC-backed startups has, I think, gotten very sober over the last 2 years as far as what happened over the previous few years. And so that's changed. Other things that you learn inside of a VC firm, I think I didn't know this at all. VC firms have this unbelievable incentive to place talent in their portfolio, and they put a lot of resourcing into having talent programs. And it is actually not that hard for an individual contributor, a manager, director, VP, CRO to get inside of the network of a premier VC firm because every VC wants to get shouted out in the board meeting. Like, my CRO came from this firm. And so this was like an aha moment for me. Like I got into Primary having not known anyone at Primary, but now I see this vibrant community we've built all over New York and there might be 3 equally good candidates for a role in our portfolio. One is very engaged with Primary, comes to an event, helps us with references or diligence on a deal or something. And the other one is sort of a little bit engaged and the other one, we don't even know who they are. And that first person gets the first look at all these jobs. So it is actually not that challenging to get in the talent network of a VC firm. And I think even for revenue leaders, I think there's a lot of revenue leaders in my network who understand this better than I did. But we ask for help with deal diligence all the time. We ask for help with references on leadership hires and individuals. And so like, there's a lot of value you can bring to a VC firm for us and then also for yourself because, you know, we obviously have a lot of opportunities, you know, roles, board seats, advisory, et cetera, et cetera.

Yeah, I'm constantly trying to do this for GTM Fund Portcos because my money's in the fund. I want to make sure that the smartest people I know are the people running these businesses. And so when people reach out, hey, I'm looking for something new. It's like, let me introduce you to GTM Fund folks. Or yeah, it could be, could be the same as Primary. It's, yeah, people, that is a great insight. Folks don't understand. I think people are intimidated by venture capital funds. Like you see them as like, oh, they, they have the money, they're choosing the winners. And it can be intimidating to try to engage or build a relationship. But at the end of the day, the incentives are so aligned. You know, if you, you want to help your friends, like I want to help my friends and former colleagues find great jobs if they're good at what they do. And these funds are dying to meet these people. And so you can actually be helpful. I think there's a friction there oftentimes. Yeah.

And one thing that is you experience in a different way inside of a VC firm You know that VCs have large networks. They're well connected. Part of their job is to know a lot of people and have networks built in different places. You get into a VC firm and you experience this and it's like, oh my God, it's a different level. And so we can diligence a founder or a company within 24 hours like that. Like the amount of access we have to getting back channels and answers and private information is astounding. And so One of the things that, you know, there are people that I try to help find their next career opportunity. And I always say like, send me a company that you're interested in and I guarantee you we can find some information, good, bad, or otherwise, that can help in your decision that would not be publicly available. So it is pretty amazing how the network of VC works and how much you can sort of get to people questions, uh, research, uh, wherever you need it. And, uh, VC firms are very, very well positioned to do that.

Awesome. Um, so we covered product-market fit, talent portfolio, access. Anything else that you wish you knew as an operator? Like a lesson, a pattern now that you've picked up that you think would have been valuable, or you're going to take into your next operator role?

Yeah, I think sort of back to the idea that we're starting Jump as a not venture-backed company. Picking is very hard, and as an operator, once every 3 to 5 years, hopefully you're now picking the next company. And when you see the process that venture investors take to analyze a market, understand where the sort of puck is going in the next few years and where the value is going to accrue and in the innovation in each category and the amount of research they put in, the amount of diligence calls they do, the amount of thesis building they do. And then I remember me saying like two of the executives from my prior company joined Compass and they turned around and they're like, hey Jason, You should come to Compass. It's great. And I'm like, yeah, sure. I'll come to Compass. I was like, oh my God. And so one of the things you can do is knowing the VC firm or people at them is, you know, that information research exists and you know that there's really rich insights coming from that. And so the benefit that I have with learning from our investment team picking will make me an unbelievably better picker in the future because of that.

What advice would you give to somebody that is a CRO today? They've just had a successful run, they've got a good profile, and they're looking for their next Series B revenue leadership opportunity. How would you tell them to go about the diligence process to make that right decision? Because, you know, like, primary might make 12 bets a year and you make 0.3 bets a year as an operator, you gotta make sure it's a high-quality call. Yeah, that's for sure.

So a couple things. One is you learn out of VC firm as well, and I think a lot of experienced CROs know this, but maybe people that are ascending into their first leadership roles don't. Leadership hires run through executive search firms, and there are a handful of executive search firms that partner with VC firms to do these executive searches. And so realistically, your ability to get access to the best roles partly depends on your ability to know nodes at VC firms and people at executive search firms. That's kind of where the the roles get originated and discussed and brought to market. So that's step one. Step two, as far as evaluating which companies, these are bets. Every single time you're doing this, you're making a bet and the more perfect the opportunity, the more competitive it is on paper. And so these are all bets. I think that, and then the other really challenging thing right now, which I'm talking to more than a dozen people about looking for their next role. AI has complicated everything. Like, it's hard to pick right now because of that. Then there's so much noise. I think the networking your way to a VC that has access to an investor deck or a fundraising memo or something, I would want to get access to that information. I don't know how often, how possible how possible that is for everybody.

You can ask the founders if you're interviewing for a CRO role. Yeah. Ask for the last, ask for the last board deck. Yeah. When I was talking to owner about this role, the founder flipped me through a board deck and then I asked for time with the COO who ran finance and we went through the growth model in sort of like segment by segment, like walk me through the metrics of the business. Yeah, that was growth and retention and unit economics and cash burn. Like, we went through a screen share and spent an hour going through the details. I think if you are interviewing for, uh, especially like a, a C-suite position or the executive sales leader, like, you, you should be empowered to ask that. And if it's a no, in my opinion, it's pretty big red flag, because the, the— as long as you've gotten late enough in the process. Like, you can't ask for the investor deck at—

I think that, that has become more standard practice, I think, in the past few years where before it wasn't like the company had leverage over the candidate and maybe wouldn't share. I think that's becoming more standard today. The other thing that might be interesting is the primary for investing, we use a framework called God of Believes in every single investment. And so we have an investment thesis. So this is what would excite us about a particular business. And it's like, it's in this category with this pain point and this You know, insight that these people have that we also agree with, that's the investment thesis. So like, why do you like the opportunity? And the debate, the research, the diligence, the underwriting is all about the gotta believes. And the gotta believes are the unanswered questions, the risks, and to say, okay, this business is going to be successful. You gotta believe that X will happen, Y will happen. These are like the real decision points in each investment. And I will use that framework wherever I go, whatever I do. I actually think it's very clarifying and at least you have a really explicit list of where you're making the bets, where is the risk and what are you betting on? And hopefully some of those bets are somewhat in your control. It's distribution and go-to-market stuff is one of the God of Beliefs. It's scaling up the revenue organization to have certain kind of coverage or unlocking certain channels is a God of Belief. And then as a revenue leader, like, okay, I have some control over that. And so that framework has been very clarifying for me and it's been fun to watch our investment team cycle through that hundreds of times in my time here.

Very cool. Have you guys shared that framework externally? I really like this gotta believe concept.

I believe we've talked about it publicly, but I don't know if we've done a full write-up on the process. That'd be cool. If we have, I will find it and send it to you.

Yeah, we'll put it in the show notes. That's a really— it's a really interesting way to look at a, to look at a deal because you have your fundamentals. Is it a big market? Is there product traction? But that's a great way to highlight, you know, what, what needs to be true and do I, do we think these things can be true with some level of, of confidence?

And a good example of this that comes up all the time is multi-product. We know what we're investing in caps out at a certain size for whatever reason. So one of the gotta believes is that if you acquire customers in this segment and you deliver the first experience, you've gotta believe that there's a cross-sell motion to a second, third, and fourth product. And so those are some of the tangible things that come up. And then part of your bet is like, do I think this is a category where and a founder where that multiple product strategy is going to win or not or something. So there's a lot of that. And then with AI, it's really hard to figure out how to play the God of Beliefs. We have a company that a lot of the viewers here probably know the founder. Amanda Caylo was the founder of Sixth Sense and now is starting—

I'm talking to her about OneMind actively.

Yeah. Great. So it, right, like this is a bet on the future. Like it's a bet that some portion of customer interactions will be done with some kind of AI avatar. And her bet is really kind of to the most extreme that like lots of sales teams and individuals or customer success teams and individuals will get replaced by an AI avatar. And so like a gotta believe is like, you really have to believe that that future is coming. Meaningful portion of the customer-facing roles or experiences that people have. And so these are the examples of gotta believes that we wrestle with internally, which is really fun. Very cool.

What advice would you give to revenue operators? So like C-level, call CROs and founders about managing VC relationships. What do you know now that you didn't know from the Compass days about how to master that dynamic?

I think it's nothing particularly wild or shocking. It's like really strong expectation setting, really strong communication. I frame everything I do with our founders as if I were the CEO of your business, here is what I would do. I try not to give advice as a coach. I say, We talk through the problem and then we say, if I were the CEO of your business, here's exactly what I would do. I think what I would say to that question is if I was the CEO of a business reporting to a board, I would be very transparent. I would be very communicative, no surprises, consistent updates, all of that. And then of course, you have to develop individual relationships with these people. And then there's a group collective relationship and the people that manage boards well, I think just do the basics really well. They have a sense of maturity, a sense of taking it seriously, and then they build individual relationships with everybody in the boardroom or adjacent to the boardroom that's also helping them grow the business. And so nothing particularly special that I would call out. Hmm.

Why don't founders execute on that? Like, no surprises, be transparent, communicate a lot. Like, why? It seems very straightforward. Why do you think people go wrong?

I think it's just extreme pressure creates moments of very— I don't know, maybe not the best decision-making or something like in the moment. Like, I think everybody— one of these things, like, everybody would agree, like, of course, like, why wouldn't you do this? And then things happen and moments come up. And it's also possible that, I don't know, a VC or a board member is not sort of being that value add back to the CEO. And so the tension can emerge from that and maybe they want to manage that person a certain way. So it's not just a one-way street, but I think it's just probably extreme pressure, extreme emotional roller coaster creates imperfection in execution. But there's like a joke and a meme that goes around like LinkedIn and Twitter with the VCs. It's like the best founders are the ones who send the update on the first of the month, every month, always with consistency, with the same metrics and like full transparency. Like, you know, it just, it makes sense. Yeah.

Our founder talks about this a lot. He's like, we never, we, he used to do it before midnight the day the month closed. And then we moved it to the first of the month. And even that was like, okay, I'm going to make sure with the board it's cool. And the board was obviously like, yeah, man, like, you know, you can have a day to get this, to get this together. He had never missed New Year's Eve. His birthday is on the 30th or 31st of the month. Like, never, never, ever missed that deadline. And it's like something in that investor update channel. He's like, we don't miss this. He's like, this is a thing that is unequivocally like needs to happen. And it, you know, just shows a level of professionalism and seriousness that if you're going to bet on a founder, you absolutely need to be there. Yeah. Okay, let's get into GTM Tech. And so I've never seen so much change happen in such a rapid succession of time. Like, it's— I was really reflecting on this. I was like, is this just recency bias? And we're always under change. And no, I'm certain that this is just a bonkers time of life. Even if you look at sort of the 2-year time horizon post-GPT-3, but even the last 3 to 4 months is arguably even more chaotic between deep-seek operator reasoning models, agents, deep research. Every couple days it feels like there's some massive breakthrough. There was some leak that OpenAI was going to release a sales agent like yesterday, and that's— it's like, oh my God, I couldn't even— I haven't even been able to read up on the DeepSeek visual, like, video thing yet because I was at an offsite. Now there's some new thing. And so where the heck is GTM going in this world post-AI reasoning agents? Like, what's your— What's your current theory?

Yeah, so I have no idea. The answer is I do not know. Same here. Yeah. And what's fun about this is I work at a VC firm and being on the ground floor of the new generation of AI-native go-to-market tech stack companies was not one of the reasons I originally joined Primary. But thank God I am at a VC firm for this AI explosion because this is the front row seat to just learning and seeing every day the next founder come into our office and explain where they think the world's going. It's a really, really fun time. It's impossible to know. Our investors are so, so smart and diligent. They spend all their time thesis building around what the future's going to look like. And if you ask them, they would say they don't know. So certainly I don't know either. What I could say though is a couple of observations that may be helpful or interesting to the audience here. First is if you zoom all the way out, we have like two decades of SaaS tools being built and deployed in every organization. And that's true of every department of every organization. But let's just talk about go-to-market tech stack. So you got the Salesforce era where you have HubSpot as your CRM, and then the vertical categories of everything got built up. There's the DocuSign category, there's the Gong category, there's the Salesloft outreach category. So there's this huge deployment of SaaS. And then what's happening now is like this huge, like retrofitting kind of thing where like AI is either being built inside of these old SaaS products or like you're buying a new SaaS product, but like connecting it to the old SaaS products. And there's going to be a few years of like figuring out like, how did the all, how does all of this like mesh together? Or do we like, do we need Salesforce anymore? Like what, you know, if we want to like move to these new tools. And it's going to be this like messy transition period. And the question is like, is it 5 years from now? Like, is all of that SaaS going to like go away? Like there's— it's kind of possible that it does. And one of the questions we're evaluating is like, are these categories of tools even going to matter anymore? Like there's a pre-sales tool and a post-sales tool and a call recorder tool and a thing. And of course you've got like this compound startup theory of what's happening. Like Rippling is like the all-in-one bundle. AI is going to do something like another level deeper than that. Like if Rippling is a bundle of all the different point solutions inside of a platform, like AI is going to start to abstract away all the platform stuff and sort of like just do work and create experiences without all this underlying architecture and APIs and connectivity. And so we're trying to figure out what does this mean? How do you invest in stuff today? What should these tools be doing with our existing tech stack, or should they be trying to replace them outright? And I think we've seen— we just pulled this stat. I think we've seen 170 different go-to-market tech founders pitch us in the last 15 months or so. Lately, every single pitch is AI-native something or other. And some of them are trying to start by replacing the SaaS analog tool from before and saying like, we're going to be the DocuSign for AI, and then we'll go do other stuff. Others of them are saying like, we're going to combine a bunch of tools into our AI-native thing. Some of them are AI-native CRMs, which is like a whole head-scratching world of like, How do you— everyone already has a CRM, so like how do you unseat those CRMs into your new— like it's just, it is true.

Can a CRM be probabilistic in nature? Like, I don't know, this seems hard, but maybe.

And then what's also really hard is that where the value accrue, like where you have pricing leverage in a tool historically, So Kyle Norton's call recorder, that was their anchor product and that was an expensive product because it was a unique product. And now there's a flood of great, amazing call recorders on the market that are very cheap. And obviously Gong is now trying to build the platform and eat into everyone else's categories. But these call recorders now are so good and so cheap. And so you can imagine each of these tools, that comes out may start with some pricing leverage because these AI workflows are new, but as an early-stage investor, you're like, what is defensible such that you can maintain pricing leverage or build a moat? Why won't this all just be a race to the bottom over and over again? Any sort of defensibility is a very, very hard question to figure out. And so these are just some of the things we're thinking about. One of the questions is like, is there going to be a tool that like truly does blur the lines between all the categories? Like, is there just going to be one mega AI tool that like eats all the other software categories? I think there's a chance that there is like because, because all the background orchestration could disappear. You don't need this big RevOps and IT team and all this other stuff. So that's the world that we're trying to sift through and it's very, very hard. But I would not be surprised if one mega GTM tool emerges at some point that basically eats tons and tons of the other workflows and apps. Yeah. Yeah.

I have sort of the same questions and similar hypothesis? Like, at what point, you know, I— people have always had their gripes about Salesforce. It's always been, you know, a tool that is extremely valuable, but like people have frustrations with. But I never thought in a million years there's a possibility that they are unseated. This is the first time I'm like, oh man, somebody could, somebody could definitely get Salesforce now because if if, you know, that's basically just a series of workflows on top of a big database. Yeah. And, and what if none of those fields matter? What if none of the, the way that information is structured and captured captures matters? Because, yeah, you know, you could just throw it all into a massive database and like query into it any way you want. Yeah, it seems like chaos to me. It gives me anxiety to think about, but There's two fun thought experiments with this.

The first is like, okay, so if you ever wanted to unseat Salesforce, I agree with you that this is the only time I've ever seen where there's like this window where it could possibly happen. But what's the hard part is that if you are on Salesforce, you have integrations and everything, every other tool is bolted into it. And this is why Salesforce was so smart. They had, they built the app store. It's infinitely customizable. You have tons of it. To unwind all that is very, very hard, especially for your like medium to large to extra large size organization. So some AI tool will come along. There's a bunch of these new startups that are like the AI native CRM, and I think something will emerge as a massive company in that category. But the question I would always ask the founders would be like, what happens when you run into a company, they're very large, Salesforce is the incumbent, they agree with you that like they're paying $4 million a year for this like massive behemoth and they would get out of it, but they just can't unwind the system. So some like magic AI offboarding tool is going to have to come along. Yeah, that like can somehow like move systems, make sure everything works the same, and then kill Salesforce, fit into every little API that's possibly there.

And yeah.

And then the second fun thought experiment, and this is like why investing is really tricky, in this because, so let's say you have a thesis that like, yeah, like data entry into a CRM is gone. There are companies, Momentum, Attention, there's a few of these companies, they watch your calls, they put the notes in the CRM for you, and we've like killed that workflow and saved salespeople a bunch of time. Okay, great. So like that's the future and we think that that workflow and technology is going to get democratized and the idea of manually data, doing data entry in your CRM is gone. Well then it's like, okay, great. So if you could invest in that, a company that's anchored on those kinds of workflows, but then what if you believe that, I don't know, there's an agentic future where lots of salespeople won't even be on calls and then the agents, whoever builds the agent company won't need those companies to do that for them. They'll just transcribe their own robot conversations themselves. And so What, what, like, if, you know, whatever this new stack of AI is going to look like, it's just so hard to figure out, like, where does it go and what does the future look like and what does it mean for each new AI capability? Like, where does the value accrue and who, who wins in that world is a very, very hard question to figure out.

Yeah. And something that I grapple with as an operator is I'm trying to be on the front edge of it all. And we have, like you mentioned, Momentum. We were there. Third, first, third, first, second, or third customer. And we've got this AI sim and we were their first call to Vara, first paying customer, their first like design partner. Like I'm really trying to be— the advantage is so crazy. And I was one of the very earliest Salesloft customers, earliest Chili Piper customers, earliest Chorus customers. I've always like carved an advantage. Like being early on Salesloft was wild. Like the, the leverage I got above most other SaaS companies and our competitors. And so we're trying to be early, but I grapple with this all the time. I'm like, is this— or is some of this investment completely irrelevant in 12 months? And should— the question is like, do you wait a little bit longer to see how it all plays out? And I've just come to the realization, like, I'm not a waiting person and I prefer to make some mistakes along the way, but be early and carve an advantage there. But I'm certainly doing it with the understanding that some of these tools might be obsolete in some period of time because, you know, I don't think it'll be Salesforce offering it, but like something else could be, could be that layer.

If I were leading a company right now, leading a revenue organization, I would do what you're doing, which is make it a part of our DNA that we are constantly experimenting with AI tooling, knowing that we're going to create some churn, some isn't going to work, but it's much better to be at the cutting edge and building internal IP around what works for our motion and doesn't. Than to wait and figure out where it all goes. And the investor distinction is important. We get to make one bet a year on a go-to-market SaaS company, maybe two. And so that's our one bet. And then that's wild. And so we have to think about what does the world look like in 5 years? If you're running a company, that is sort of irrelevant. You can find— the hard part though is filtering all the noise and figuring out what's the one or two pilots I want to do right now. But I would absolutely be aggressive with that. And we did this thing a while ago at Compass for a sort of similar purpose. We called it like the Sales Lab. And for a few months we had a few top sellers of maybe the top BDR, a RevOps person kind of like in the lab, partly because they wanted to be the experimenters on behalf of the whole group and tell everybody like what worked and what didn't. And that's probably what I would be doing right now if I was running sort of like a scaling up organization. Organization. I do think that there will be some of these like AI agencies that get to like very, very large scale helping companies figure out the exact right combination of AI tech to implement. I think those businesses are going to like explode in the next few years. Yeah.

Yeah. It's going to be interesting because some of them have no idea what they're talking about. Like I see some of the thought leader people putting out, they're like, oh, I wrote a prompt for this. And I'm no prompt writing expert, but like, I can read, read some of this stuff. I was like, yeah, this is sort of crap. Like, it's either too generic enough to be helpful for anybody's business, or it'll give you an output that's like a cool party trick but actually not like materially helpful for a rep or, or a leader. It's, it's, it's going to be such a challenging period of time for, for leaders because like, you and I, I think, have a predisposition to be interested in this stuff. Like, you know, I've been advising and investing for 5 years or more and have built enough pattern recognition to understand, like, when I pick a really early stage company, it's really like a founder bet and I'll do a pilot and I'll give the founders a bunch of feedback and I'll see how fast they implement it. And I'm trying to align on like a vision. Do we have a shared vision of the future in this category? But I think most people just look at tools and like, this is cool, this will be helpful, and then they send it. And you can end up with 3 or 4 tools that— and it's just mass confusion across your team and very little value, and you've wasted time, energy, and money to sort of get nowhere. And so I don't— I— somebody was asking me for advice on this topic, and my advice was like, dude, you got to go learn to be— you got to learn to be a venture capital investor, basically, to like know how to choose early-stage tech or maybe just wait.

Here's one way you could approach this, and we're doing this at Primary right now for our business development team. One way you could take this is say, okay, let's map out our supply chain of how our go-to-market works. So like from marketing to SDR to sales to conversion to post-sales, and where are we either like spending an outsized amount of time or where's the place in that entire workflow that we would love to create leverage? And the example from Primary's business development team is they're spending 15 hours or 20 hours a week just in Sales Navigator. So like their business development team functions like a BDR team basically. And 15 hours a week they're in Sales Navigator and then they have 5 or 6 other hours spent on the prospecting motion. And so—

Clay.com to the rescue, baby. Yeah.

So for them is go find a tool or a workflow that gets you from 15 to 20 hours down to 5 per week per person. Like it's gotta be sub-5. And so they have like a specific problem they're trying to solve. And now we can go out to the world and say like, hey, all the new AI apps, here's the exact thing we need to solve. Who can do this for me? And they're taking demos with those companies. So that's one way to think about it is like, go out to that world with a very specific problem to solve and then see what you find in that arena. Because otherwise everyone needs a filter right now. It's too overwhelming. There's too many tools. They all have some sort of overlap with each other in some ways. So you have to pick apart what each one does better than the other. It's very, very hard. And that's why I think AI agencies will— there will be some that emerge that will be unbelievably huge because people need a trusted filter to say, don't worry about the noise. You're paying me because I'm going to review everything and tell you what you need. I think that is going to be a— there are going to be some $100 million revenue AI consulting firms, I think, in the next few years. Yeah. Yeah.

If I wasn't so locked in and excited about Honor, that might be something I'd go start because I love the space and I feel bad for leaders. That is just so confusing. And the other advice I give to leaders is like, you just have to make this a priority. It's not really a choice. Like, I sent Andrej Karpathy released like a 3.5-hour video on the foundations of LLMs, how it works, what's the difference between pre-training inference and what's a token and how does this whole thing work. And I sent it to my leadership channel. I'm like, you got to watch this because everybody has to have enough foundational knowledge about this toolset because it's going to be the foundation of how we all operate in the course of a couple of years. It's like being like, I don't really need to know how a CRM works. It's like, no, no, no, that's part of the job requirement. And so you got to find the time. Yeah.

The other thing that I think we're starting to do a primary, and I've talked to a few people who are doing this in their companies, making AI like a theme at the company and whether you're an SDR in HR, in finance and legal and sales and leadership, Making it like whether it's department or company level, like, hey, this is the time of AI right now. Like this is the year of AI and anyone that has AI breakthroughs, hey, here's what I was doing before I found this AI workflow. I'm trying it and now it did this new thing for me. Here's what after looks like. Being visible, celebrated loud inside of a company, like that's what I would be doing because then it motivates other people to be like, ooh, I would love to find that for my job. And I think that would be a really fun way to do it inside of a company. Yeah, for sure.

Okay. I could also do another hour on this topic, but we got to go to the quickfire. So you've gotten to work with a bunch of CROs through Primary and through your operating career. In your mind, what separates a good CRO from a truly great one?

Interesting. It is situation dependent. I would say that the hardest skill set to find in a CRO is the classic is the best salesperson type at the company, best sales leader, and then the CRO, like that path. Finding that person who is deeply analytically fluent and P&L fluent is very, very hard. And so A really good CRO certainly can be excellent at building, managing, and inspiring the sales organization and doing all the mechanics of talent development and all that other stuff. I think the best CROs have pretty rich analytical fluency about the numbers and mechanics of the business.

I have that in a Substack article on the topic. I couldn't agree more. Amazing. What's the most common advice you're giving to, uh, let's talk about founders that are, that have just found product-market fit and are starting to get into figuring out go-to-market.

Um, the common theme, the most common theme, I think there is a standard playbook that everyone is used to. It's like founder-led sales, hire your first AE and an SDR, hire 2 more AEs, maybe then hire like a player coach AE, then hire a VP sales, and it corresponds to the funding rounds. The thing I'm trying to do is for each business, figure out if that's actually the right plan for that business. I think there are some businesses where the founder should be the sole salesperson until like $5 or $10 million ARR, and they should actually surround themselves with like other people. And there are other variants of this. So it would probably be to question the sort of traditional playbook and let's really have a sharp and precise point of view on is that right for this business? And if it's not, let's find what is. I don't think it works in every scenario.

Yeah. That's really interesting. What's the hardest lesson you've had to learn?

In my career or in private?

Yeah, in your career.

Going to law school, realizing it wasn't for me, and jumping into the tech world when my family, friends, and entire network sort of said, you're a lawyer and this is who you are. I took my medicine early. I struggled for a few years paying back loans and financially, and I still have an extreme amount of paranoia. About if you're not like proactive about your career and you don't, you don't like have a vision for yourself, the world will push you around and you'll be, you'll be following other people's visions. And so like taking my medicine early on that front has saved me a lot of pain downstream, I think.

Yeah, for sure. What's the best thing you've read in the last 12 months?

Two of our investors at Primary, Brian Schechter and Tobias Citron, they're our AI and infra investors. They invest in the deep tech and the infra on AI. They write this newsletter every month called the BNP Newsletter, Brian and Tobias, and it's just like they were not experts in AI when this started, and it's them documenting their learnings, their questions, their areas of exploration for the last 2 years. and it's like, I, this is like exactly why I joined a VC firm to like learn from people like this and to like, to see that they were not experts. They're not technical. They're not engineers by trade and they're learning this world. It's like, okay, it's not that scary. And they do such a good job with like clarity of thought and taking you on the journey, the learning journey that they're on. So I would, and it's public. Anyone can read it.

I'll share the link with you.

What's it called? BNT? The B&T News Infra newsletter.

Okay. Yes. I didn't need another AI-related newsletter in my life, but I can't resist. Yeah. So that's good. Jason, this was awesome. Where can people find you? What do you want them to go read? Plug, plug, whatever you got.

Yeah, sure. You obviously find me on LinkedIn. I've started to do a little bit of writing on there with with mixed emotions, but I think I have some things that I could share that could benefit other people. And so I'm starting to do that. And then my company Jump is jumprevenue.com. We just launched recently, so it's just a placeholder website for now. And at Primary, we will meet early-stage founders even as they're ideating. Like, we want to be very early and with you on your whole journey. And people that are starting a company, I'm always happy to chat with and see if we can help in any way.

And tons of awesome content on the primary site too. Yeah, you guys push out some like actually high-value stuff, not just, not just SEO content to try to rank. Like it's, it's— I've read a bunch of primary content over the years and it's, it's legit. Thank you. So All right, well, this was awesome. I really appreciate you joining, and, uh, we got through a lot and there were still like 4 hours of podcasting we could have done on some of this stuff. So appreciate it.

Yeah, thanks so much, Kyle.

Thank you for listening to the Revenue Leadership Podcast. If you enjoyed it, don't forget to subscribe, and you can find a link in the show notes. And be sure to leave a 5-star review, share it with your network, and please join me next Wednesday for another great conversation.