How to Hold the CRO Seat for 6 Years with Jeff Perry

In this episode of the CRO Spotlight podcast, Warren Zenna sits down with Jeff Perry, Chief Revenue Officer at Carta, to unpack the harsh realities of modern revenue leadership. Far beyond the standard industry playbook, they dissect how the traditional path of relying on massive sales headcounts has become a liability rather than a badge of honor. Jeff reveals why the modern revenue leader must prioritize extreme efficiency.

Their conversation explores Carta's fascinating evolution from a singular equity tool into a multi-dimensional platform serving diverse stakeholders. Jeff explains the complex mechanics of scaling entirely new business units simultaneously without losing operational focus. By shifting away from standard growth metrics, he illustrates how true cross-functional alignment outpaces simply adding more quota-carrying representatives.

Addressing the notorious turnover rate of modern revenue executives, Jeff shares hard truths about why the role is constantly misunderstood by boards and founders. The discussion highlights the dangers of resetting leadership repeatedly instead of fixing fundamental system flaws. By sharing his own long-term success strategy, he provides a contrarian blueprint for surviving and thriving when the organizational ground shifts.

Finally, they tackle the polarizing impact of artificial intelligence on relationship-heavy go-to-market strategies. Rather than forecasting an automated apocalypse where software fully replaces human interaction, Jeff argues that trust-based selling is actually becoming far more valuable. He challenges leaders to relentlessly audit their technology stacks, favoring in-house innovation over unnecessary third-party sprawl.

What is The CRO Spotlight Podcast?

The CRO Spotlight Podcast examines the CRO role from both sides — the companies that hire them and the leaders who take the seat. Host Warren Zenna, founder of CRO Collective and author of “What Chief Revenue Officers Actually Do,” brings diagnostic frameworks and pattern recognition from working both sides of the equation to every conversation.

Jeff Perry Podcast Transcript

Warren Zenna: Hey, this is Warren Zenna, the founder of The CRO Collective, and we've got a great guest today. We have an amazing executive, Jeff Perry from Carta, the CRO of Carta. He's been around as a CRO for six and a half years, which I think is like one of the longest tenures of a CRO that I've seen in a while.

He's been at Carta for like almost eight years, and he's got a great story, a really amazing career, and very insightful, and he also happens to work in a really interesting space for segmentation of, you know, compliance, governance, finance, and innovation, and it was a really great conversation.

So listen in and thanks for listening. If you don't mind, why don't you introduce yourself a little bit? I mean, a lot of people know who you are, but it'd be interesting to kind of give your amazing career you've had and kind of an interesting run you've had over the last, like, 15 years or so, particularly over at Carta, where you probably have, in my view, like, one of the longest CRO tenures I've seen of anybody I've spoken to. So that's something I want to get into, but why don't you do that a little bit for the people listening?

Jeff Perry: Yeah, sure. So yeah, I'm born and raised in the Bay Area here and I'll start there because, you know, I grew up in Belmont, right across the street from the Oracle buildings. And I ended up going to Santa Clara University and got out of school and spent a couple of years at Merrill Lynch.

Ironically, some of the sort of part-time tasks I had at Merrill Lynch were working the cashier window, where back then in call it '98 to 2000, clients actually used to bring in cash, checks, or physical stock certificates to be received by Merrill Lynch to be deposited into their accounts.

I share that 'cause it's kind of ironic. You know, twenty-five years later now, I'm at the company that eliminated the actual physical stock certificate. And it also, for me, career-wise, it was sort of, you know, one of these sort of triggering moments of, I remember a man came in and deposited a stock certificate, and I did the calculation on it.

It was eBay. Beautiful stock certificate. Yellow, red, blue, green, perforated stenciling off of the certificate. And I remember the calculation, it was worth somewhere around $225,000 in stock, that piece of paper. And it got me thinking, like, "This is really cool for him. I wanna go somewhere where I'm getting equity and have an account like that someday."

And so one thing led to another, and that led me to, through some connections and, you know, network, an opportunity to work at Oracle. And I did booth and exhibit sales and sponsorship sales for the OpenWorld conference. And I did that for a few years, and then simultaneously, I had a bunch of friends from high school in the area that were in product sales in Oracle.

And they kept hounding me like, "You should come up and be a part of our team. Maybe you'd be great at it." And I was like, "I'm not sure. I have a pretty good gig going here. Like, you're putting me on a real quota where I could potentially get fired. I'm not sure I'm ready for that." But one thing led to another, and I ended up making that move to the inside sales organization at Oracle and spent, you know, about 15 years there in a variety of different roles.

Multiple times asked to do different things and lead different teams or build new teams. I had an opportunity to help sort of rebuild the sales teams when we acquired Sun Microsystems, which was a great sort of career opportunity for me to kind of do what felt like a startup inside of Oracle.

And I think that actually, I didn't know it at the time, but it kind of gave me the itch to like, how do I get to a smaller company where I feel like I can make a bigger impact? And ended up having a chance to move over to DocuSign. I spent four years there, and I helped scale the SMB organization, and then took on working on some of the verticals as well.

And then that kind of same itch came back after the IPO at DocuSign, was like, "Wow, I'm still putting in the same amount of effort as I did in the early days at Oracle, but I feel like I can make such a bigger impact at a smaller company." And there was just something that really resonated with me, and so ended up leaving DocuSign and found Carta, and Carta found me kind of simultaneously.

And had, you know, a much smaller company and a chance to really help, I think, build the company now and see it evolve from what was, you know, originally selling cap tables when I first met Henry. And we were trying to just win the rest of the cap table market, and now it's multiple products for founders.

It's fund administration for venture and private equity. As of, you know, three or four months ago, we bought a law firm as well. So it's sort of multi-buyer but also multi-products inside of each of these ICPs that we work with. And it's all obviously interconnected between founders, investors, and asset allocators.

So I've gotten to do a lot of really fun, cool stuff, and I think we've built a great team here. It changes every day. Carta's, you know, fast-paced. So we still operate like we're a startup in many ways, and it's been fun to see the growth trajectory. When I started, we were about $20 million in revenue, and, you know, things go our way here, we probably end up somewhere north of 600, probably 650 to end this year.

So yeah, a really good path. Yeah, and then there's so much more coming too with all the things that we're doing with customers.

Warren Zenna: That's amazing. That's a great story. And you know, a couple things you said there I wanted to touch on. So you said something which is interesting. You said, you know, "I don't want this job. I'll have a quota, you know, I can get fired for that," right? And you know, I understand. I mean, it is a riskier proposition, you know, for the right person.

You know, this, if you play your cards right, it actually really pays off pretty well, but it's still risky. So what made the leap for you? Like, why did you decide all of a sudden that risk was no longer like a problem? Why did you make that shift? That's a pretty important one, you know?

Jeff Perry: Yeah. You know, some of it I think probably was just a little bit of like gaining sort of business self-confidence. I think I left college with confidence. I played baseball in college and, you know, as a Division I pitcher, you have to be fairly confident to stand out there and actually do that.

So you know, I think I was probably finding sort of my own way in the business world and like, you know, there was a role that I had that was, you know, a bit more stable and secure, and I think finally I realized like, okay, for the future, I also saw like the earnings potential of others or at Oracle and how successful they were, and I felt like that had a different path and trajectory for me than the role that I was in.

And so at some point it was like I also just looked at some of the people around there and I was like, "I feel like I'm seeing these people do it and do it well. I think I can do that too." And I always was like, I think pretty good at finding, you know, mentors or people that would help me and support me, and I feel like I, you know, with the right kinda network of people around me, and I joined what was, you know, a team mapped to selling to enterprise accounts, so Fortune 500 accounts at the time.

And I had a really small group of people that helped really support me and teach me, and then from there it was like no looking back. And...

Warren Zenna: I understood.

Jeff Perry: Yeah, then, you know, probably did that for two, probably two and a half years or so, and then someone, I know who they are, that like just decided, "Hey, you should maybe be a manager."

And I didn't think I could do that either, but someone saw some ingredients in me, I think, in sort of how I operated and how I ran my business as an AE, that I could potentially be a manager. And so the, you know, first opportunity to do that and sort of never looked back from there from a leadership standpoint as far as my career path and the roles I pursued and also really found like what I love doing and enjoy doing.

Warren Zenna: Okay, that's really great. I mean, I asked that question for a number of reasons. The main one, you know, that we're gonna be talking a lot about the CRO role today, and, you know, the sort of profile of a CRO, like the traditional profile, which, you know, you obviously fell well into. I think of myself as well, right?

Salespeople who grew up in the sales organizations and took these increased risks and a different type of mentality than someone who's kind of getting paid for the work they do as opposed to earning the money they make through the opportunities that they can create and that risk profile.

How much of that do you think today's modern CRO needs to have? And I ask this question from this context, right? So traditionally, the CRO came from sales. I mean, this is like where all CROs came from, probably for, I don't know, since the entire instrument was born. That's not the case at all anymore.

I can tell you now 'cause I do this, I'm speaking to CROs all week. I mean, that's all we focus on is this role here. And we're seeing the profile changing a lot. Like a lot of people now don't even come out of sales. They come out of RevOps or come out of marketing, or they come out of other types of...

Or even products that some of these people do, you know? And mainly because the risk profile of the business is different. You know, it's much more of a politically risky role than it is more of a compensation risky role. Mainly because the competencies have changed. It's very numerical, it's very data-driven, it's very spreadsheet-driven.

And also what's happened too is, sales leaders who come into the role have a tendency to entrench themselves in sales activities which diminish their ability to scope on the other things that are outside of the sales function that CROs need to focus on. And if they can't get out of that, they tend to, you know, lean too much into the sales organization as their strong suit as opposed to looking at the entire revenue operation.

That's a different brain to be able to do that. And so I'm asking you this question because I'm curious, are you seeing the same thing? Like you're in this role now for a really long time, but what's your sort of general... You're talking to a young person, let's say, someone who's like 20, you know, and they say, "I wanna be a CRO one day just like you."

You know, what would you sort of say? Would you say, "Well go get a sales job?" Or would you say what? How would you guide someone to the role given your perspective on it right now?

Jeff Perry: Well, I think I would say, "Are you sure you want, like, less hair and a gray beard and all that that comes with it?"

Warren Zenna: I'd say the same thing. Why the hell do you want this job? Yeah, that'd probably be the...

Jeff Perry: Yeah, so that would be the starting point of the conversation. But the reality is, you know, I get asked this frequently and, you know, it's... To me it's kind of an amusing question because the reality is when I started at Carta, we didn't have a CRO.

Actually, I remember Henry called me, I think, like a week before I actually started and said, "We hadn't really talked about your title. What should it be?" And we kind of landed on the vice president of private markets at the time, which made sense for the cap table business, and we didn't have a CRO, we didn't have a CMO.

I think Charlie had just been... actually, no, he was not even CFO at the time. So it's just the stage Carta was at, at the time, and I wasn't overly hung up on the title, right? And so I've always just taken... This is the advice I would give to that young person that you're talking about, is like the title becomes what it is over time, and I just think, like, if you immerse yourself in trying to learn the business, both, like, on the customer side, on the product side, on the people side, where you can find growth drivers and, you know, when you first step into the role, where you can find low-hanging fruit to help the organization immediately and make an immediate impact.

Do all the good work, and then the title stuff and the compensation and all those things come along with it if you're doing the right things on a daily basis. And you know, it's worked out for me. Maybe it doesn't work out for everyone, but I feel like that's just general sound advice that I give to anyone in, like, an individual contributor role or a leadership role.

Like, you have the role you have, do a great job, be the best you can possibly be at it, and that will open a door to whatever the next thing was, and I always treated it that way. Now that I've had the CRO title for, I don't know, five years or whatever it is now, you know, I do think, like, how I think about sort of what I do day-to-day has changed.

A lot of it early on is like, you know, you're working with, like, deep in pipeline reviews with AEs and things like that. And then as an organization gets bigger, now we're doing things that, you know, you're thinking about the strategy of the business. Like, how are we doing with, you know, integrating the four acquisitions that we've made over the last nine months and making sure that, number one, they're successful as acquisitions, both from the people integration and the product integration standpoint.

And then you obviously just wanna prove that the acquisition was valuable, so making sure that from a revenue perspective, it's sort of showing its worth. But more importantly, which I love about Carta, and Henry has helped us with this so much, is like it's become less about, like, prove to me that you can drive X amount of revenue so that we can show that X acquisition was valuable, which more like CEO, CRO thinking is like, how does it actually fit into our overall product set and make it a better product and a stickier product and a better experience for our customers?

The revenue part will work itself out, like assuming we go position the product in the right way and help customers understand why it's a good thing for them. And so that's more like the CRO thing versus the, you know, sales manager, head of sales, VP of sales, whatever the title is. So yeah, I don't know. I just never got overly hung up on that.

Warren Zenna: Thanks again for listening to the CRO Spotlight podcast. We're excited about all the great guests we have, and more importantly, we're excited mostly about you for being avid listeners and supporting the work that we do here. Feel free, please, to share the CRO Spotlight podcast with any of your colleagues.

We just think there's a great wealth of information here, and we want to get the word out to as many people as possible, and your support of the show is really appreciated. I wanted to share information about a program that we offer called the CRO Masters Council. The CRO Masters Council is a bimonthly group of six seasoned chief revenue officers who are looking for a chief revenue officer board of directors, so to speak, that they could share what's going on with them, collaborate with ideas, get some feedback on what's going on in their current role.

And these are great conversations. I facilitate them. The CRO Masters Councils, again, they're twice a month, and they last for at least six months to a year. So if you're interested in having your own CRO suite, your own board of directors of chief revenue officers, it's a private, confidential conversation that we have.

It's infinitely useful. Imagine having a room full of other chief revenue officers you can talk to and say, "Hey, I'm working on this," or, "Have you guys figured that out?" Or, "I'm having this issue right now with my business or my results." These are just invaluable conversations with chief revenue officers.

Chief revenue officers have a very, very unique role. It's a very lonely job, and only other CROs understand what you're going through. So that's why we created this program. So if you're interested in being a member of the next CRO Masters Council, which we have a number of them being put together right now, just go to my LinkedIn and DM me Masters or Masters Council, and I'll follow up with you and set up a call or send you some more information about it.

Looking forward to seeing you there, and thank you.

Warren Zenna: No, it's great. And I think that what you described is exactly what more, I say, you know, 'cause, let's just kind of for the sake of semantics kinda get clear on what the definitions are and what we're talking about, 'cause we do have pretty specific things here. And the reason we do is not everybody's in the same situation you're in where they have a leader like that.

You know, most of our clients don't. What they do is they go in a situation where there's a board, and there's a PE firm that has an extremely structured way they run every company, and every title has a specific reason and a specific way that they're slotted and paid and compensated. You know, it's a system, you know?

And so they get slotted into it. Now that system has to be somewhat, you know, transmogrified for each different company, but they're trying to run things basically the same way 'cause that's how it works for them, right? It's a factory to some extent. And it works, right? They get their multiples, they move out, they go on.

But if you're loaded into that sort of an environment, you don't have the ability of someone to say, "You know, just do your job well, and we'll figure it out." They're like, "Okay, you do this, and you don't do that, and you're gonna do this. You're not gonna do any of that, and go for it," right?

Jeff Perry: Yeah, yeah.

Warren Zenna: So what ends up happening is the CRO role is uniquely difficult, as I have to tell you, because of the following, right?

So one is, if in fact we've already agreed that the pipeline for CROs is mostly salespeople, they're coming up through a sales organization where they've demonstrated the ability to continue to grow revenue through acquisition models, and they can do that well. Great. We like that about you. There's a lot of competencies associated with that, right?

You can persuade people, you can manage pipelines, you can manage teams, you can hit a number, all that stuff, and that brain is good for us for that role. However, when a company gets to 40, 50, 60 million, that stuff is important, but it's part of a system. It's not the system. It's a piece of it. And if I'm gonna run the whole thing, I sort of have to know how the whole thing works, not just that one piece.

And that's where the brain changes, and all of a sudden the person's competencies may no longer be a fit. And if you don't have that defined, and this is where I'm getting to, as clearly enough, that person can sort of drift into a lot of different roles without any real, like, actual distinction. And six months or eight months later, that person's in some different job with the same title but doing different things because they just drifted over there, and then all of a sudden they're looking for somebody else.

And this is usually what we find is happening right now. That's usually the reason. So the earlier on, if you're not in your situation, which God bless you, you are, you sort of have to be an advocate for defining things clearly enough so that you can carve out the way in which you have the right authorities and autonomies and scope and resource allocations and timelines that you need to do the job.

And so we're seeing that this is where the failure rates are, is that even if someone's really, really competent and they get this job, if the system that they're brought into doesn't accommodate them properly, they can get thrown all over the place, and they can get kicked out regardless of how good they are.

And I know that if you're a good performer, they're probably gonna keep you around, but then you've gotta be a lot more flexible around the way that you're being allocated every day because it can change. And I think that's the big thing we're dealing with here with the role we have. So I just...

I said a lot. I wanna know what your thoughts are on all that stuff.

Jeff Perry: Yeah, no, I mean, a lot of thoughts on it, and you're so, you're so right. And I actually feel very fortunate the situation that I'm in now, and some of that is just kind of like consistency and familiarity with, you know, most of the board members have been pretty consistent since I've been here. I can't tell you how many...

You know, there were early days where I would come to a board meeting and then two or three of them I wasn't at. You know, most of it was taken care of by Henry. Now, you know, the last couple years I've been on every board meeting, and I know all of them, and I know, like, what they're gonna ask, and I know what they're thinking about.

And so, you know, you kind of like to guide the talk track of, you know, what you want to convey and share with them, but also what you know they want to hear and what they're concerned about, right? And so some of it is just being able to do that on a consistent basis. I also think that, you know, a big part of something that I personally just learned in how I think and operate is in this sort of nominations of $100 million businesses, and that's something I learned directly from Henry.

It's like the things that we're doing... We had the cap table business, and that was well on its path to becoming a $100 million business, and I helped scale that, you know, without doubt. But then it was like, what's the next one that you can make the next $100 million business? And if we're gonna be a successful multi-billion dollar company, we have to have multiple business units that are well beyond 100 million in revenue to be able to be sustainable like that.

And so now that's what I spend a lot of my time working on and thinking about doing. Not as much on the CapTable side of it that we already have that going. I have a fabulous leader and team that runs that business. I'd put it up against just about any company in the world as far as efficiency and productivity.

Where I spend my best and most productive time is on some of the other businesses that we're gonna make even bigger than that first CapTable business that we have. And you know, some of it just comes with life experience, business experience, maturity, confidence to know, like, okay, trust the people that you have running that and go spend your time in the places where you can make a greater influence, and that just happens over time.

And I think that's one of the things that, you know, I'm very fortunate having been, you know, at Carta for eight years and in this role with the title for, you know, five years. It's not lost on me that it's unique. But I also think there's a benefit in having it be unique. I think, you know, from what I've observed in the industry, there's this trigger of like, oh, the CRO lifespan is 18 months.

Well, that's fine. Bring in the next, you know, guy or gal for, you know, 18 months, 12 months because it wasn't working out or whatever, and you've literally reset back to zero in most cases, right? And...

Warren Zenna: You absolutely, you have to. You...

Jeff Perry: You have to, but you wonder why, like, a lot of these things fail. It's because you did the reset, and you did the reset, and, like, there's never any consistency.

There's never any, like, standards or processes built. And you have to be careful because as a startup you don't want too much process because you don't want to stunt entrepreneurship and be nimble and all those things. So I think there's a balance to be, like, keeping the core of sort of what got you to where you are, but then also having the consistency and the stability of process and repeatability that helps, like, get me where I am.

And I think, like, there could be some lessons learned from that along the way too, you...

Warren Zenna: There's no question. And you're right, and this is exactly what happens, right? So, you know, the whole predicate of this entire thing we created was to help think of that exact problem. Well, there's two. One is that the definition of the role is just completely, it's like, it's spaghetti sauce, you know?

You can make it any way. I like arrabbiata, you know, like a little of this. You know, it's like, no, you know, you make it one way 'cause this is the way it's supposed to be. But then it's also, there's a stage component to it, right? I mean, CROs at different stages have different jobs, and they should. And they have different competencies and all sorts of things.

And so there's a lot of awareness that needs to be brought to this role because the thing is that, again, I'd like your opinion on this, you know, we believe very strongly that there is a point at which you need a kind of singular revenue leader. That doesn't mean that the person does everything, but it's just the person who runs the revenue organization, right?

From a leadership standpoint that has a very clear understanding of what the goals are and how the system is gonna be architected and built and the way it's gonna operate, and all the pieces are gonna fit together and how things are measured and how the machine works. And that person also has a direct relationship with the CEO and the board, and that person's responsible for overseeing all that.

And like you, they probably sit on top of it and do a lot of other larger things, but they've set a system up that they know produces a certain result based on the customer outcomes on a consistent enough basis that they have a good understanding of what each person fits into. It's a football coach, basically.

It's a Belichick guy. Really, it's what it is. But, you know, you have to get to a point where you have a big enough team of, you know, 11 players on the field to be able to do that. So if you're a startup, you're not going to. You're probably gonna run a sales organization. But those changes between those stages are very difficult for companies to understand.

It's also difficult for CROs to come into an organization and know where they're being slotted into and what's being required of them, and those two missteps tend to be the issue. And your point is correct in that the organization tends to blame the candidate as the problem, and they go find another one.

They hope that'll fix it, and they don't look at the system that they're giving that person to run. So I'm curious, like, what are your thoughts on that? Like, you're running an organization, you wanna bring in a CRO. How do you evaluate what we would call your CRO readiness to make sure that you know this is the right role and how to operate it so that it lasts six years?

I mean, someone did it with you. That's what you really want. That's the ultimate outcome here.

Jeff Perry: Yeah. No, and you know, someone, Henry did it with me, and frankly, at a company that at that time there was a lot of exec turnover. That has subsided, but I could have easily been, you know, just one of those other situations, right? And so I think some of it is like, you know, you have to earn the trust, and then the trust has to be allowed for you to earn as well, and I think that happened over time.

And you know, I think, like, yeah, you're right. Like the founder, board, whoever's hiring for that stage of the company, I think it has to be really, really honest about what they want and what is needed at that moment of time for that company. And then if you can project out X time period and say, does this person that you may be interviewing or considering, can you see them projecting out to fill that need at that same time?

And then these are hard questions, right? Like, do you know that that person's gonna pan out or not, or is the business gonna be the same or not? Like, who knows, right?

Warren Zenna: Probably not. Yep.

Jeff Perry: That's the risk and/or the calculated risk you have to take as you... And that's how I would go about thinking about it.

And like, no one could have, you know, met me in 2019 and said, or, you know, '18 actually, and said, "Are you the guy that could do, you know, cap tables?" Which was kind of like what my core experience was. It was the, you know, the DocuSign type business, SaaS software sale. But can you also, you know, scale to become, you know, understanding fund admin?

And that's a different cycle. It's a different ICP. It's a service and software. It's not just software. And then could you also be the guy that can help integrate a law firm and start selling those services to multi-billion dollar private equity firms? Like, no one can project out whether you can be the right person or not.

But at some point, all these different things and the years of experience, I think have helped me somewhat almost become a little bit of a unicorn for the role, because there's no one out there that knows each of the different pockets of the businesses that we now do, right? So you'd never be like replacing an apple for an apple in this case.

So part of it is like, do your job, try and do it really well. And like I said before, like having the best interests... I always say this to our team too. If you have the best interest of, you know, our customers, our company, and our people in mind, and you're making decisions off that, and you're putting your daily activities around those three things, how can you possibly go wrong?

And if it does go wrong, then you're probably not at the right company or they didn't hire the right person. I don't, you...

Warren Zenna: Yeah. Look, we're in agreement here. So, you know, I'd be curious to know too, so you and I are probably a little close to the same age, and, you know, we've seen just an incredible amount of change underneath our feet within the organizations that we worked at for the last 20 years.

You know, now is like one of the strangest times I've ever seen, you know? And I thought I'd never say that. You know, I always thought like, you know, that sounds like some, you know, old person saying that. You know, "Boy, things are weird," you know, that kind of thing. But, you know, it really is. And so, you know, we're seeing an unusual amount of acceleration and innovation and usage of different tools and the way people are going to business and the way people are building products.

I'm curious, how are you looking at that right now? So if you're, again, like the context is important here. You know, the people listening to this conversation are typically people who are probably newer to the role or looking to be in the role, or maybe they've had the role for a couple years and they're thinking, "Boy, I'd love to have Jeff's situation."

You know, what would your point of view be on what it is a CRO needs to be thinking about right now when they're looking at a job that frankly is just changing underneath their feet?

Jeff Perry: Yeah. Well, first and foremost, it's like the team that you work or hired with. So, you know, who's the CEO, founder CEO? Like, are you working directly with that person, and do you believe you have a partnership with that person? That's first and foremost. The second would be like, to me, who's the sort of surrounding team?

And this is a concept I never thought about in my earlier and younger years and career, which is this concept of your one team. And I've always thought like, you know, I played baseball in college. My team was my team, the guys I played with or that were in the dugout with me. And when I went into business, it was the same.

My team was like the team that reported to me. And I learned this concept several years back that was more like, sure, you're always gonna have that. Like, I'm always gonna have my team. But if you think about it, the team I'm on is actually the exec team. And so if you start thinking about the exec team more as like your peers and your partners to help get the stuff done that helps make the team below you do better and be able to perform better, that's a really important relationship and bridge to create across the exec team.

And we had times at Carta where that worked a little better than other times or sometimes not as well. But I think right now it's in a really, really good place where everyone works really well together as our one team. So that's a big part of it. And then the third is, I think we can't like not to touch on this, but like what is really different and unique about the job, and I've thought about this a lot as far as it would pertain to my own career too.

You know, when you're at Oracle, how you're perceived is like how big your team is and how much headcount you have under you. That it's like you could look it up in the system like, oh, so and so has X amount of people now. They must be really important, doing well, right? And I actually feel like it's the complete opposite in today's world.

If you can take and leverage the best of what you have in the company and then using your product team to build products faster, and you can leverage all the good things that AI is bringing to organizations, whether it's around product build or efficiency and go-to-market tools, you actually are better at your job if you can do it with less people.

So that headcount thing that was like the status thing has actually totally reversed in the last twenty-five years.

Warren Zenna: Okay. It's almost like the new metric is how many agents does that guy oversee? Wow. That's a lot of agents.

Jeff Perry: And or how efficiently can you-- really you're gonna do six hundred and fifty million in revenue and you have this few people? Or what, you know, people would perceive as a much lower amount than you would expect to have, right?

Warren Zenna: Yeah. Yeah.

Jeff Perry: I think, and the encouraging thing for all the CROs that might listen to this or aspiring to be is, you know, and I've had many people talk about this that I didn't think would actually subscribe to it, but the role that AI is struggling with really replacing is the salesperson.

And I think it depends on what your product is and who you sell to and all those things, but at least for us, the relationship sale is not going away. The relationship is... It's only becoming actually even more important, where we're creating what we call like Carta change agents, where we're sending people out, people part of go-to-market orgs and our product org together to actually build the relationship and teach people AI and how we're doing it and where the industry is going.

That tells you how much more important the relationship is even becoming. It's not becoming less because we have AI.

Warren Zenna: Hey, everyone. I wanna thank you again for listening. I get great comments across LinkedIn and other channels about the show, and it's really gratifying to see that we're having an impact on you. Another thing I wanted to let everybody know is that we also produce events. About two and a half years ago, we started these CRO roundtables, predicated on the idea that...

Well, two premises. One is that CROs are looking for other CROs to talk to, which is really true. It's a very lonely job. Now, how do we get a bunch of CROs in a room where they're not being, let's say, disintermediated by panel discussions and sponsorship events and demos and stuff, and really give them a chance to talk to each other?

So we created a roundtable event that is essentially that. It's a three-and-a-half, four-hour discussion between 20 and 30 chief revenue officers, and these are amazing events. The format took off. People love them, and I get requests all the time as to when is your next CRO event? So to that end, I just wanna let y'all know that we have a number of roundtables coming up over next year, over the next, like, 2026.

I wanna share them with you so you can, if they're in your market, you can come. So the next one we're having is gonna be in London, actually, in February. February 24th in London. So if you happen to be a chief revenue officer in the UK or even in Europe and you wanna come by, you'll be hearing about it more on my website and my LinkedIn.

But throw it on your calendar. And then following that, we're probably gonna be doing an event in San Francisco in March. There's gonna be one in New York in March. I'm gonna do another one in Chicago probably in April, and then I'm gonna do an event in Boston. I'll do an event in Atlanta. I'm gonna do an event in Salt Lake City.

I'm gonna do an event in Austin, and I'm gonna do an event in Los Angeles or the Southern California area. So those dates are to be determined, but they'll be going across all next year and these events are taking on huge momentum. They're the place to be if you're a chief revenue officer and you want to be in a room with no interruptions and have an opportunity to really share with each other in a sort of a private and confidential, open discussion about everything that you wanna talk about as a chief revenue officer and collaborate with great people.

So thank you and thanks for supporting the show and I look forward to seeing you at the events.

Warren Zenna: I completely agree. There's no question about that. I mean, this is why the event business is booming right now. There's dinner every night now. It's crazy. You know, people don't wanna talk to Claude anymore. You know, they wanna talk to people. But at the same time, it's interesting that you say that.

I mean, I have my own opinion about it, but, you know, given your perspective and where you sit right now, do you think that, like, let's say from the PLG motion, is it gonna be an entirely, like, machine-led sales organization pretty soon? Is that what's gonna happen? I mean, I probably don't have to really speak to a person a lot.

I mean, think about how many things we buy that we never talk to anybody about. But, you know, big decisions, larger sales, larger software deals that have a little bit more at stake, not just, you know, buying a pair of sneakers. But, you know, getting $10,000 or $50,000 a month, you know, products, is it gonna be done through agents, you think?

Jeff Perry: So I think there's a couple ways to answer that. Number one is like, and this is a question we ask ourselves, is whenever presented with a tool of some kind, and should we evaluate this tool? Our question has always become, and Henry sort of forced this through the organization, which I think was brilliant, which was, send me a video, three-minute video of what the tool or solution does, what it will replace, why it makes the current process better as a result of us using it.

And then he'll watch the videos and say, "Okay, this is something we should maybe talk about, should we buy?" Right? But if you're gonna buy it, then he asks the next question of like, "Okay, is this something we should actually buy, or can we just build it instead?"

Warren Zenna: Can we make it? Yeah.

Jeff Perry: And so like the layers have gotten even harder and harder, which, you know, that's gotten us... We had tech sprawl everywhere, and this helped us sort of bring that back home of like only going and investing in the future of other tools or technologies that, like, we couldn't build on our own or were gonna significantly impact the business. And so we instilled that across the organization.

And I think it made us, you know, a hell of a lot better as far as efficiency and everyone getting on the same page of what we should be doing and using, you know, for the future.

Warren Zenna: Yeah, it's a good point. I mean, we have the same thing. You know, we're mostly really in the consulting space, so we're not building, like, products per se, but we are 'cause they have to have a format and, you know, there's things they have to do. You know, there are pieces of the engagements that require, you know, data ingestion and analysis, et cetera.

And so, you know, we've had partners who have technologies that enable us to help do what we do, and now we're like, "We can make that now. We don't need that partner anymore," and it's not that hard to do. That's a huge shift, and that creates a different brain. Like all of a sudden we're like thinking, "You know, we don't need to spend money on that anymore.

We don't need to divide up our revenue to partner. We can do it ourselves." And that's a shift I'm seeing happening quite a bit now. Quite...

Jeff Perry: That begs the question like, okay, did that AI instance eliminate a job? No. It actually either changed a job or it created others to do something differently, right? Yeah.

Warren Zenna: Jobs in my opinion. It's not eliminating them. I...

Jeff Perry: So like the PLG thing, like there are certainly products out there and companies out there that like the PLG model that works 100%. I'm hoping I'm not too biased here, and I just not just have my Carta hat on, but I feel like what we do specifically is a bit unique as far as the product that we offer and who we offer it to. And I don't think you can go to PLG with a... You know, I tell the team this all the time. If you're a founder of a company and you've got a three-person company, you have your great idea, you, you know, you're 26 years old, you've got a little bit of funding, and the most important thing in your life is probably your cap table.

Like it's not your family and your cap table, right? Everything you've done to this point is like building this company, and it's like your thesis statement and your mission statement and your pitch deck and your cap table. The last thing you're gonna do is probably go onto some website and be like, "Yeah, I heard I need cap table software and issue equity and do my 409A valuations, and let me just upload it to some website somewhere." Like...

Warren Zenna: It's too important.

Jeff Perry: By the way, all these founders, like they want an advisor from Carta. They want a trusted person from Carta. So...

Warren Zenna: No question.

Jeff Perry: Fortunately for us, there still will always be that founder touch point. And then what we do on the investor side is very similar. A CFO making a huge decision on how they're gonna run the back office of their firm, which is basically the spine of the firm, doing that through PLG is not gonna happen without some type of relationship and someone actually like, especially what we do, which is different than just signing up a new account and hiring more accountants to service the work.

We do it through software. That's what Carta is. And so we have to teach some of these folks what we do, how we do it, where the industry is going, especially with AI, and how we will do this in partnership with them, and that starts with the relationship.

Warren Zenna: Yep, agreed. There's no doubt. I mean, if you're in an inherently relationship business, you're actually in pretty good shape today because it's gonna never end. People need to be, people need to be around. I just do think that the middle stuff, the administrative, tasky stuff, that sort of segment is increasing.

Like it's creeping into other things, which is fine, I think. I don't think it's a bad thing. I don't have any negative opinions about this. I don't see a dystopian... I see dystopian stuff being more like we just don't talk to each other that much anymore. You know, we're sitting around all day talking to machines, which I think I could see happening.

And we're gonna buy robots and stuff soon. I mean, hopefully I'll be, you know, pretty much almost dead at that point, but it's gonna happen, right? So in the meantime, though, you know, I'm seeing a lot of salespeople who are now outsourcing their entire SDR teams to agents, right?

Which I think makes a lot of sense, right? Now, these people who were SDRs, they're gonna find another way to work in the same model in a different capacity. I don't see them being out of work. They're just gonna have to shift their skills and find something else. So I don't see this apocalyptic thing. In fact, I don't think all these big, huge layoffs and stuff were necessarily driven by AI.

I think these were bloated organizations that had too many people. They always hire more people. They're pulling people off the marketplace to keep them from other people hiring them, and they can afford them, and they give them stuff to do, and then all of a sudden it's like, "Well, we reached our plateau, so let's get rid of them now."

And they did it at the right time to say, "Hey, you know, AI," and really like it was just a write-down, you know? I don't think it's what people thought. But anyway, I do think it's fascinating though, because your industry is heavily regulated. So there's other aspects of this.

So how are you guys dealing with all the, you know, governance and whatnot when you're dealing with this particular space? That's gotta be really complicated.

Jeff Perry: It is, yeah. I mean, you know, that's the core of what Carta does. I mean, we handle financial information, whether it's for founders or investors. And so, you know, everything we do to security is prioritized in, you know, how we handle that information that we have from them and then, like, what we do with that data.

And really, we haven't used data to create additional products yet, aside from one area where... Well, there's two things to that. Number one is we have one product, our total compensation product, where we've taken anonymized data of cash comp and equity and created the greatest compensation benchmarking tool in the world because it comes from fifty-five thousand cap tables that we have on the platform that is updating in real time.

So it is the best of the best, and that's where we've used data as a product. You know, the rest of what we've done data-wise is actually just, like, our wonderful insights team here that shares data to the industry on state of the state of all things happening around funding cycles, type of companies being funded, size of funds, which ones are successful, length of fund, life of funds.

Like, all of that we have because we have twenty-five hundred firms also using Carta and fifteen thousand entities on Carta. So we've used the data to actually become a better trusted advisor to create better relationships with customers and prospects. So we have to be very careful with it. The security of it is extremely important, obviously.

You know, we have an incredible engineering team and a compliance team. But you know, that's how we operate with it.

Warren Zenna: Yeah, it's another possible $100 million business for you guys, fintech governance tools. I mean, it's gonna be needed.

Jeff Perry: Could be in the cards, yeah.

Warren Zenna: You guys probably have an incredible amount of data with which to determine what the right way to do it is, and everyone's gonna need it, so something to think about. But pay me on that one when you do it.

But that's big. I mean, we have a couple of fintech clients of ours, and this is just their big issue right now. Plus also healthcare too. It's a massive problem right now.

For them. Some of they're being told, "You can't use Claude in the office. You can only use, you know, I mean, a copilot, you know, 'cause we have a Microsoft agreement," and they kind of like hold the insurance policy against that for us and stuff like that.

So I'm seeing a lot of these interesting things go on. But so, just to switch gears before we kind of end up here, appreciate this. This has been really fun. So, you know, if you're talking to like a CEO or a board of an organization, and they're nearing the point at which whatever you may determine is the answer, where a CRO is probably a good next hire as the organization gets more complicated, what are the ways in which you'd guide them on how to evaluate hiring...

Not just finding the right person, but making sure the position is designed in a way that it actually makes the impact that they want it to make, and what are the considerations they need to take into account before they start just like throwing out that title and start bringing somebody on to do that job?

Jeff Perry: Yeah, I would definitely, you know, as I think about my relationship with some of our board members, I would probably just try and rewind, you know, back to call it 2019, '20 and say, "At this time when Carta hired Jeff in '18, like it was VP of sales role sort of standard for the industry." Like that title and role was fine.

It was to run the engine, scale it as fast as you can. That changed pretty quickly within a year and a half, and has just changed even more over the last five on top of that. So you know, I would say take a look at what is needed in the moment to scale, but then more importantly, if you're looking for a CRO that can understand multiple business lines, how to make those operate together, understanding that they're all gonna be at different phases of growth.

They're gonna have their own variables of challenges. They're gonna have their own variables of things that go well. But someone that can kind of stabilize all of them to get you these multiple paths to multiple hundred, $100 million businesses. And then I think, you know, part of it is like admittedly, I didn't have great experience prior to like the...

You know, at Oracle, I didn't have exposure to RevOps. It was part of the machine, right? Like RevOps was behind the black curtain that just happened for you, right? At DocuSign, a bit more exposure to it. At Carta, you're basically involved in leading it, RevOps, sales ops, enablement, all those things.

Like that, the person that has to be your CRO is someone that understands all of those functions and how they work optimally really well together, right? And you know, currently I'm leading our demand gen team, and that's something that I didn't have before. Now I do, and I think it's great. Like we have an opportunity to make sure that everything that the demand gen team is doing and all the budgets that they're spending and all the different things, search, live events, where we show up in industry events, all these things, are they all doing the right activities that are helping generate top of funnel or progressing existing pipeline to close?

And that's it. And so us working more closely together, me having an opportunity to be much closer to that team, I think is that much more helpful. And so can you find, as the board member or the hiring founder or exec team, can you find the person that can understand all those functions and how that puzzle needs to work really well with those pieces put in together?

Warren Zenna: Great. Well, insightful and appreciated. And again, so everyone knows where you work. What are you working on, and what would you like everybody to know a bit about so you can make sure that that gets communicated across everyone listening right now?

Jeff Perry: Yeah. Well, thanks for the... I enjoyed the conversation. Thanks for the opportunity to chat with you. And yeah, you know, Carta has changed so much. You know, as I mentioned, the cap table business, you know, continues to do really well. Our fund administration on the venture capital side, really doing well.

We've put a ton of focus over the last two years on the private equity and private credit portion of the segment. So there's a lot more work to do there. Every month now, we're winning new big private equity firms onto the fund administration platform. And then we're also adding in the acquisitions that we've done, like we acquired a CRM to add to the fund administration platform.

We do K-1 taxes for firms as well. So most people think of Carta as like the cap table business for founders, and it is so much more than that. And then, you know, lastly is Carta Law. And if you think about, if you're a firm that is spinning up a fund, all of the basic compliance and risk legal services you have to go through to start that fund, we now do that through our AI law firm, and we'll do that at basically a fraction of the cost to be able to do that.

And those are repeatable things that we can do much more efficiently and at a much better cost for customers. And so kind of becoming this one-stop shop for venture and private equity firms to be able to run all the things that they need to do to start a firm and spin up funds as they need to.

Warren Zenna: Great. Well, amazing career. Thank you so much for your insights. Really great to meet you. I'll be out during Dreamforce. Who knows, we will bump into each other. And thank you. I really appreciate it. And I don't know. We'll see you soon. I hope that we get a chance to meet sometime face to face.

Jeff Perry: Likewise. Thanks so much for having me, Warren. I appreciate it.