E22: Designing a GTM Strategy for Multi-Product Companies with Jeff Perry, CRO of Carta

And today's guest is Jeff Perry, who is the CRO at Carta. Jeff grew up at Oracle, where he spent 13 years from a lowly rep to a VP of sales before an almost 4-year stint at DocuSign, where he was a VP of commercial SMB sales. And Jeff has since been with Carta for the last 6 and a half years, with the last 4 as the CRO. And Carta has exploded while Jeff has been there, growing from around $20 million ARR to $450 million today. And he owns sales, solutions, engineering, business development. He's got his hands in a whole bunch of stuff. And I'm really excited about this conversation. So, Jeff, welcome and thanks for joining.

Hi, Kyle. Thank you for having me. It's great to see you again and be here to talk through revenue with you.

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.

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Yeah, and there wasn't a lot of sales machines like the Big Red Machine at the time, you know, cranking out reps with that type of acumen. So that must have been a cool experience in, in the heyday of it. It was, yeah.

I mean, I probably didn't realize it at the time because I was younger and less experienced. And, you know, getting Oracle on the resume and going through the training regimen that they provided at the time, I didn't realize the invaluable experience I was getting at the time. I, in fact, still have friends, one friend who was given advice from a mentor. He was born and raised in the suburbs of Chicago, and he was given advice to actually pick up your life, move to Redwood Shores, the Bay Area, take any job at Oracle that you could to get that training under your belt. And then he did that for a couple of years and then had an opportunity to move back to the Midwest. But that's how important the regimen and the baseline for the sales skill set that Oracle was providing at that time did for myself and so many others.

Awesome. That's cool. So what else did I miss in your background? Anything that you want to fill in on that?

Yeah, I think, ironically, the part you missed was that right out of college, I actually started working at Merrill Lynch. And, you know, I didn't really know exactly what I was doing. I was a classic, like, graduate from college and, you know, figure out sort of your path from there. Sales or sales leadership wasn't a major in college at that time. Still not at my college.

Still not.

Yeah, maybe it should be. And so I was fortunate enough to get a job at Merrill Lynch. And ironically, I was trying to learn the business, great opportunity to learn under more senior people. And I just tried to be the person that would work hard and hustle in the office. And that's sort of tied to my baseball background and growing up and playing in college. And I'd work the cashier window later in the afternoons after the market had closed. And I bring that up because it's ironic that all these years later, I was actually like taking physical stock certificates and depositing them into people's accounts.

Wow.

Fast forward almost 20 years and I'm at Carta, the company that helped eliminate the actual physical stock certificate and make that a digital process.

Yeah, that is quite the full circle moment. That's cool. And so you played, you played baseball in college. That's cool, too.

I did, yes, at Santa Clara University.

What position?

I pitched.

Oh, there you go.

Which I think actually is a really nice metaphor into like sales leadership because for me, like baseball provided this ultimate team atmosphere, team experience. But also as a pitcher, you have so much control over the outcome, good or bad, of the game. And I think that very much ties into what we do as sales leaders, where you have the team component of it and you're driving the team. But so much of it heavily relies on like how you think about the business and how you perform as an individual, very much like being a pitcher and the influence that you have on the game.

Nowhere to hide as a pitcher. Nowhere to hide.

It also teaches you some, I think, some humility along the way because you have some good days and you have some bad days. And I think that creates some consistency throughout as you work through like a tougher month or a tougher quarter and having perspective on like not riding the highs too high and the lows too low.

Yeah, I come from a mixed martial arts background. That'll definitely teach you a lot of the same lessons. You got it. You got to be real humble and getting beaten up, beaten up every day for years and years.

So yeah, I definitely had a few good games under my belt, but I also had a few tough innings and tough at-bats as a pitcher out there and gave up a few long home runs. And so you got to be able to sort of turn the page and move to the next hitter. And I think that's It's very much like what we do. It's maybe not just on a monthly or quarterly basis, but like in my role, just sort of problem solving every day. You got to be able to like help solve the problem task at hand and then turn the page and move to the very next one.

Yeah. Yeah. That's a great lesson. And so the topic we're going to dive into today is multi-product strategy and then using that as a launching pad to talk about organizational design. And I had Dini Mehta from Lattice on to talk multi-product and they've actually taken a different org design to that challenge. So I'm really interested to unpack how you've come to this different framework at Carta and why, and more around how you think about making decisions and what is the data and the mental models to get to the right thing for the business as it matures. So, you know, Carta has evolved tremendously from $20 to $450 million in the you know, years you've been there since 2018. Just give folks an overview of Carta's business because I think most folks aren't going to know that they have 3 distinct lines and all of this other stuff. So just walk us through it.

Yeah, it's whether I'm explaining Carta internally or externally, I like to frame it as sort of almost 3 different companies, but so intertwined together because we're basically building a platform that brings founders, funders, and investors of funders all together. Um, but as far as like how the company operates on a day-to-day basis, we think about the, um, the corporations business, which most people traditionally knew Carta as when it started as eShares over 10 years ago. Um, and that is the cap table software, bringing early-stage, uh, founders onto the platform, taking a, uh, what was an archaic, uh, paper process or Excel spreadsheet process and putting that cap table into software and then issuing the, uh, equity grants to investors and employees of those companies. Um, and so that's company one, the corporations business, and we have over 40,000 companies on the platform now. And over the last few years, we've been able to add in additional products to be able to build a cross-sell, uh, upsell growth function of that business. And then company two started roughly 2018, '19, which was, okay, we have this connectivity between founders and funders. Let's start working and building out our own general ledger for, uh, fund administration for venture capital firms. And because we work with so many of those firms and their portfolio companies, it was easy for us to start building a product around the needs of the CFO in those VC firms, which we did. And that business has also now quickly grown and, and we've added products and through an acquisition of Tactic recently, we've added a tax product as well. So we've added that cross-sell function inside of, of sort of business number 2. And then business number 3 is sort of a combination of both, which became, um, LLC portfolio companies that were coming inbound to Carta because they had a very similar ownership tracking problem like a typical venture-backed C corp did. How do we track the ownership of our company? And we used our cap table product, which was sort of good enough at the time to be able to help them track that ownership. And it allowed us into this sort of private equity LLC space. And then over time, we started to be able to build products not just for the portfolio company, or we built one specifically for LLCs to cater to the needs that those type of companies have, and then also built products for the private equity firm themselves, waterfall scenario modeling so that they can track all of their investments. And then of course, we do fund administration for the private equity firms like we were doing for venture capital too. So that's why I say it's kind of a combination of the three. And then there's a bunch more stuff that we're talking about in the future. And sort of the missing node to all of that is the LPs. And so that's what Carta is all about, is building this platform for the CFOs to be able to bring the networks together of founders, funders, and investors. Hmm.

And where does the comp benchmarking product— is that run across all three then? Is, and is that, do you consider that a separate SKU or how do you fit it into this taxonomy?

Yeah, good question. It's actually a separate SKU in, uh, the, the corporations business, but it is very much tied to the other businesses as well, because you can imagine venture capital firms are very curious about making sure there's consistency in compensation across all of their portfolio companies. So we actually sell the product to portfolio companies, but we also give some— share some of the information with venture capital firms as well because they want to make sure there's consistency inside of their companies. And it's really multipurpose. You know, what happened is over years we were able to Gather all the compensation data through the live cap tables that we have on our platform, and then we link the HRIS system. So we're really the only platform that is able to give real-time equity data and compensation data that is up to cap tables updating live. So if you're a typical Series B company and you're going to hire a director of marketing, our total compensation product can tell you exactly what the market says that role should be paid. And it's multi-benefit, right? Like, if you're the candidate, you know that you're being paid fairly to the market. If you're the founder, you know that you're also paying fairly in the market and you're protecting your cap table and giving away the appropriate amount of equity for that specific role in mind.

Makes a ton of sense.

Which is why that product, like, has different— it's interesting because it has different personas that we would sell to. You're typically working with a founder, VP of finance, or CFO on the cap table side. The compensation product, oftentimes it's some of them, or, and/or it's the someone that's related to like chief people officer or HR type of use case instead.

Yeah, yeah.

And that's just allowed— that's allowed us to sort of expand our, our conversations and our relationships inside the customer.

Cool. Are there any other SKUs that live in any of these products that are upsells or cross-sells as well?

Yeah, we also have a tax advisory product and a QSBS assetation product for the corporations.

Is that Tactic, the QSBS?

No, Tactic is on the, the fund administration side. So that's modeling and planning and reporting for, for funds that are being raised.

Okay, very cool. And we're going to get into the org design and who sells all these things and how it's all shaped. But I think this is really helpful. Um, and what's the rough split of revenue across the products? Like, in terms of maturity, is it, is Carta like 80% the corp business and these are fledgling other arms, or how, how does it get split out? As much as you're comfortable sharing.

Yeah, so I would say, you know, right now roughly, uh, two-thirds of the revenue comes from the, the core business of the cap tables. Um, you know, another 25% or so comes from the venture capital fund administration. And then about 10% from the private equity business. And so like that's the corporations business, very consistent. We bring on roughly 500 new companies every month into the platform. And then we of course do cross-sell and upsell to those companies. And then the growing businesses are, we've taken sort of the same formula. If you think about the corporations business, it was built off of Finding early stage founders, get their cap table onto Carta, and if they're successful and as they grow, they become larger customers for us. And so we took the same mentality into how we built the fund administration business, which was you don't go win like Andreessen, Sequoia, Accel, all the big firms on day one. We started with win the first time fund managers and emerging managers, and we had a ton of success there. We have over 2,500 individual logos on the venture capital platform right now. Um, and they all have multiple funds. So we have well over 10,000 entities actually using, and on that, that platform now. Uh, but it really started by using the same mentality that we had for the corporations business, which was win the early stage founders, uh, sorry, funders and, and get them on the platform. Uh, and then if, you know, their funds are successful, they'll add fund 2, fund 3, et cetera. And they grow with us. and that's now allowed us to work more what we call upmarket as well into a more enterprise version of our sale. And then taking sort of the same philosophy of the sort of the best of both worlds as we've done that on the private equity business too.

Yeah, I would imagine not as many emerging private equity businesses as a, as opposed to, you know, the emerging manager craze, you know, exploded in 2020, 2021 in VC.

It's, it's definitely different. Um, but we are finding, uh, a lot of traction with, uh, sort of first-time fundraise in in private equity too. The, the funds themselves tend to be a bit larger, uh, than they were on the venture side, but there are first-time, uh, fund managers that are spinning up now. Yeah, and it's actually a great opportunity. Like, our space in this ecosystem and sort of the responsibility of Carta, we feel, is to help educate whether you're a founder or a funder. And so we provide a ton of content for each of those individual groups on you know, how to raise, what are the steps you're going to go through as your company grows or your fund grows, which is why it's important that we continue to add additional products to help add more value to them.

Yeah, Pete Walker's content is some of my favorite on the internet in terms of venture. It's— that's a powerhouse.

Yeah, Peter is— he's a special employee for us and he's created quite a following and deservingly so. And it's mostly because people are starving for the data and he's able to put that out in a way that is consumable. and understandable for people to really get the insights coming out of the, the true data. But, uh, he's, he's turned himself into a rock star, so we love having him on the team.

Yeah, yeah, yeah. It used to be Crunchbase. It was like just Crunchbase that had cool venture insights like this. And now, yeah, I think, I think Peter's giving them a run for, for their money.

And the best part is that, you know, everything he puts out is coming right out of Carta data, uh, lives in our platforms.

Cool. So similar formulas. All right, cool. Let's move into multi-product strategy. So when did these different product offerings get spun up?

So I'd have to sort of answer in like by components of each of the different businesses because the timing was different. It wasn't all simultaneous.

Yeah.

And but I think sort of the net of it is like, I don't know that anyone in go-to-market has solved the exact right like org alignment to solve this problem. And I've done a little bit of each of it along the way, my steps at Oracle and DocuSign and now Carta. And there still isn't a silver bullet of like, here's the optimal way to structure the organization. I think you need to like really dig in with the data and the analytics of like what's working, what's not working. Uh, one of the things I absolutely love about Carta and what Henry, uh, our CEO constantly encourages us to do is experiment. And, you know, he's instilled a philosophy of like, go ahead and experiment, but learn and learn fast and be nimble and move and make adjustments based off of what you're learning. And so what you might think is like the optimal way to align, which could be like you have sort of a core rep and then you have an overlay model, which is something I had in my, in my Oracle days as an example. And when I first thought about org design at Carta, that was my natural response, like, here, how I've done— I've seen it done before, we should go with that model. And the reality is that that wouldn't have worked for us. I don't think at that given time it might at some point in the future, but for us now it was like, let's make sure we've enabled all of our AEs to be able to, to communicate the value proposition of the entire stack. And we're able to do that. And then we've supplemented that with building out a solutions and solutions engineer organization, which are deeper product specialists that are able to assist our AEs in discovery, uh, and in technical explanations of the product. Uh, and that's something, well, over the last, call it 18 months, 2 years to 18 months, is something we've built out as a function as part of our revenue organization. It did not exist in my prior 4 years here at Carta.

Oh, interesting. Okay.

And frankly, that's because it wasn't a, a real need of the business. And so as the needs started to arise, we adjusted the organization accordingly.

Mm-hmm. And so the corporation's business, you know, that's, that's from founding 10 years ago. When did the, when did the funder and LLC PE businesses get spun up?

Yeah. So the venture capital business fund administration spun up in late 2018. 2019 really started to take off.

And then the PE business.

And then, uh, the private equity one, I would say, was sort of happening as the corporations business was coming in from the Portco side. Uh, in the last, call it 2 years, we've actually dedicated teams, uh, to, um, to number one, educating that market. And that's the biggest thing now. Like, if you think about the stages of these sort of 3 companies within, they're all at different stages of maturity. And so corporations is like, maintain and optimize as best as we can and add value to those customers versus private equity, which is educate a market on all the things that Carta's platform can do to solve for both the firm and the portfolio company. Perfect example is about 2 weeks ago, we did a mini takeover in New York City, the private equity section of New York City, and took over a coffee shop and invited everyone in the private equity network to come by for a cup of coffee and just start to build the brand awareness in the marketplace, uh, for, for firms that in some cases traditionally didn't think of Carta as, um, you know, an option for them or something that could help their firm or their portcos.

Makes sense.

And that's, you know, that's where we can get into like the difference in, you know, how we do marketing for the corporation's business versus venture capital versus private equity. And they're also in different stages of maturity too.

Yeah, I, I, I'm definitely going to get there. So I, I want to just, uh, start at So when— so you've been doing— you've been putting more muscle behind the PE business for the last 2 years, but it was sort of percolating. What was the trigger for you to say, hey, we have to carve off product, go-to-market, all of these resources to make a bet here? Like, how— talk me through the decision-making there.

Yeah, so it started more on the portfolio company side where we knew there were K-1 distributions and different functionality that a portfolio company would need that was an LLC. And then we started realizing most of them were primarily owned by private equity firms. So that allowed me to spin off a team of my corporation's business that just focused on LLCs that became the private equity business. And so that's why I say it was kind of happening simultaneously. And then as that was happening—

What was the trigger? Like, what made you say, like, we need to spin those people off?

Well, I think it's a couple-fold. Number one is roughly 10% of that business was coming to us inbound. And so we were getting a signal from the market that there was a need for us to specialize in that way. I don't think at that time— actually, I know at that time we didn't know we needed to specialize as far as like make it its own company, but we needed to specialize creating a team inside of the corporation's businesses, which, which is what I did. And that was probably 2.5, 3 years ago. And so we sort of specialized inside a corp and then spun that out to make it its own business unit over time. And that's, you know, we've gone back and forth at Carta on functional model, business unit model. At that time, we were in a business unit model. That allowed us to spin out product, marketing, engineering, everything to support— properly support building the private equity business.

Okay. So you had dedicated product marketing sales efforts just for this business unit. And does it roll through a GM or does it go through— product is still under a CPO? Yeah.

Okay. It's business unit, but it gets functionalized sort of at the top.

So matrix.

Yeah, exactly. Yeah.

Okay, cool.

Which, you know, we've, we've gone back and forth on models. You know, another thing I don't know that anyone has perfectly solved on, like the exact model that you go to market with. And it's something we've changed over time too, based on, you know, the needs of the business at that time.

Yeah, that makes sense. And so it was the pull of the market telling you you needed specialization, but why not just have existing reps do it? You felt like the buyer was so different or the conversation was so different? Like, what was the trigger to say like, hey, I need a dedicated rep for it?

Yeah, I think some of the specialization in the product was like the really the igniter for us saying like, build, make this its own team. And then at the same time we were doing, you know, you mentioned like the pull, like we got the pull from the portcos, but at the same time we were starting to do the push to the firms and we actually didn't know really how to go to market at that time. And so over time, we've created sort of a tops-down and bottoms-up approach where some of these portfolio companies will come directly to us, and that allows us a way to be able to start communicating with the firm that owns them. In other cases, the firm takes much more control over the portfolio companies, and we have the relationship with the firm, and we built a business development team that, that supports those relationships. And that's sort of the top-down motion. And so it's very different than sort of what we were operating with in the venture capital space. versus the private equity space.

And so then what was the trigger and what was the data and decision-making to say, we're going to take this from a couple dedicated reps in the corp business to now all of these additional resources?

Yeah, I think the biggest thing was knowing the, the opportunity and the TAM, um, because like in venture capital, I, we, I can't create more companies or create more rounds of funding for them. So you're sort of, they are limited, sort of time-bound or buying-moment-bound to those couple triggers. Um, and the private equity space was just much, much larger than the venture capital space. So we knew that there's a greater area of opportunity there if we started to dedicate and push resources in that direction.

Okay, so it's TAM, and you decided that you could get more of that TAM faster if you dedicated certain product efforts, certain go-to-market efforts. Like, how sophisticated was the analysis on that? Or was it just like clear, hey, like, this is obvious, we got to go do it? Or just—

I'm not sure that it was. Yeah, it's a good question. I'm not sure that it was completely obvious. However, like, there was enough signal there for us to know. And what's going to be the next thing? Like, Carter wasn't just going to stop at the corporations business and become like a really nice couple hundred million dollar business. We already have that. Now it's like, how do you become a billion, a $10 billion company? You take over these additional markets while you continue to supplement with adding products and starting to do M&A in some of these spaces as well.

Okay. Makes a ton of sense. So let's get into that question around marketing. So you've got 3 different, very different levels of maturity. And so how are you taking them to market differently?

Yeah, well, number one, I have an excellent marketing partner here. Nicole Bayer is our CMO and You know, I think sort of when you think about sales and marketing, there's this natural, like, there must be conflict with the two. And you hear about that a lot amongst my peer groups. And I actually don't think— I know I don't have that here. I have a great partner. And so we strategize on how do we go to market into these, these three different segments and who are we marketing to. And as I mentioned before, the corporations business is a steady state. And so there's an awareness piece, there's a brand piece. It's not as much like account-based marketing. It's more of educating on new products or sort of where we haven't penetrated the customer base with additional add-on products. That's very different than like the private equity. We need to go create brand and awareness in the market and make, you know, have speaking engagements for our exec team, do, you know, the coffeehouse takeover, things like that in the, the areas of the country where we know private equity is predominant. Those are like creating a brand to make everyone think about Carta like they think about Carta from a cap table perspective.

Makes sense.

We also, you know, over the past, call it year and a half, I think we've changed our, our philosophy on like how to market to, to upmarket or larger enterprise firms and, you know, higher-touch events. We've done a lot of those things. We've done client entertainment type things to— and not just because like you want to sort of schmooze one of, you know, a CFO or a customer, but really like bringing communities together. And I think we're really good at that. Like when we bring a pool of 10 or 15 CFOs to a dinner, they are genuinely curious about what their peers are working on and how they work with Carta and what the platform is all about. And so it allows us to create these pockets of networks um, in across all three of the businesses that help us build more pipeline for the future, but also build a tighter community of existing customer base.

And how distinct are the sales motions between those three businesses?

They could not be more different, to be honest.

Oh, really? Okay.

Uh, well, parts of it there's crossover, but in general, um, I think about the, the corporations business, uh, you know, dealing with an early-stage founder. They're typically what we would think of as an SMB, uh, sale. Um, they move much faster. Our average sales cycle is roughly 14 days. Uh, there's a lot of one-time closes. There's a very strong referral network between, uh, VC firms and law firms. Uh, and so things just move really fast. It's also a high-volume, high-velocity business, um, running on a monthly cadence. That's very different than working with large venture capital firms or private equity firms that operate more like an enterprise business on a quarterly forecasting model. The sales cycles can be, you know, 90 days to 18 months. And so it's more about the building the relationship over the period of time and proving out the technology. So that's a new muscle that, you know, Carta and my team is learning as we've built these businesses.

There's a lot happening in, in, in Carta.

There is, yes.

You know, 3 different business units, multiple add-on SKUs. Bunch of segments within it, you know, the emerging manager versus trying to go land Sequoia, I'm sure. I mean, couldn't, couldn't be more different.

Yeah.

So how do you, how do you manage it all as the CRO? Like, how do you keep all of this stuff cohesive in your head and build strategy and like juggle it all?

Yeah, I don't know that I've solved it by any means, but, you know, I've actually thought about this. Should I sort of break up my week, you know, have like corporate operations day, a venture capital day, a private equity day where like all of your meetings are only focused on that. The reality is like that's probably not practical to do. Um, so I think, you know, every half hour, hour increment, uh, tends to be a different problem to be solved in each of those, um, businesses. And that's how we've approached it. And, you know, I think, uh, part of Carta's OPITs, our operating principles, you know, one of the things on our original office when I joined was, was be helpful. And I feel like this company exudes that more than anywhere I've been, which is lean in and figure out like what we can do to help each other solve whatever problem is at hand. And that's allowed us to like move quickly and adapt and evolve based on whatever challenges are facing us.

So what's your reporting cadence like? How do you even just keep track of what's happening in all of these businesses? Because you've got forecasts, which has a more well-known well-known rhythm, but in terms of the project work and if strategy is on track or not, like, how are you keeping the flow of information to yourself? Yeah.

So, you know, I think about that in multiple ways. It's like, how do I keep the flow of information moving down? But also, how do I manage sort of up and around the exec team as well? So I have sort of the traditional, like, you know, we have a forecast meeting on Fridays, which Frankly, those are a bit of an update meeting because I feel like I am so deep into the forecast. Like, I don't need that meeting to tell me exactly how things are going. Um, you know, because, because we're living it day to day, uh, and especially with some of the larger deals. So we're kind of facing the classic, like, you have the run rate business that's fairly predictable, and then you have this, this new segment, which is these larger enterprise deals, which take a little longer and create some variability in the forecast. And As we continue down this path of potentially becoming a public company at some point, we want to create the consistency and the repeatability and the predictability in how we forecast. So we're kind of like building those motions along the way of like being more consistent. And then like weekly, I'm doing an update to the exec team on state of the pipeline. We're about to launch a sort of a bowtie mentality of thinking about sort of top of funnel, and how that pipeline progresses to closed deal, and then lifespan, um, of expanding wallet share of, of a customer along the way too. So, um, those are the things that Nicole and I combined, um, go-to-market sales and, and marketing, uh, present to the exec team. Um, and then I have, you know, a series of, of, of meetings throughout the week that are, um, sort of project-based of like the, the main tasks at hand that I know need to to move the needle, to move the business forward.

Okay. And so do you have 3 different strategic plans for each business unit, or like, is there an enablement plan and there's different things under that? Just like, how do you conceptualize what needs to get done? Because I feel like that's the hard thing for me, is to keep everything in my head that we've said we want to do. And do I have to go back to the strategic plan every single week and have like, you know, go line by line? How do you think about it?

Yeah, we do. And that's how I operate the business. I'm fortunate to have a really strong strategy team. But, and, you know, we just came out of the end of last year, which was like the planning cycle for the upcoming year. And that's really how we think about it is, okay, how are you breaking this into 3 different components? And like, what is the target that we're trying to get to for the corporation's business, for venture capital, for private equity? And then you build backwards from there and say, okay, Okay, if these are the goals that we're trying to get to, what are the things that we need to do and accomplish inside of each of those businesses? And then also identify the risks inside of each of those businesses that would prevent us from getting to those targets. And then we just cross-check against that on a monthly basis. Like, are we doing the things we said we were going to do? Or, you know, inevitably new things come up and then you make adjustments along the way because not once in my 20-year career has everything played out perfectly how you've outlined it at the start of the year. That just doesn't happen. And so you have to be flexible along the way.

Yeah, I'm still waiting for one of those years where it just goes.

It doesn't really happen.

Yeah, we were 3 weeks into January and I was like, goddamn, I'm basically throwing out big parts of my 2025 plan because one of our, one of our like longer range bets started to just absolutely rip like months earlier than we thought. And like, okay, Well, we're going to reorient around this.

The other, like, interesting wrinkle to Carta— not that it wasn't complex enough, but if you think about these models, you know, the corporations business operates very much like, you know, traditional SaaS company would. Very high margins, very profitable. The venture capital business is different. It's a combination of two. It's software and services. So it has a very different margin profile than the corporations business. So a lot of the things that we're working on doing now is making sure that we are creating the best possible experience for our venture capital companies that come on board onto the platform and that they're using and leveraging the tools that we have available that help us make them a more profitable customer, but also help them be a more efficient customer for themselves too. And so we have some basic things like using some of the banking vendors that we have integrations with that eliminate a bunch of errors on the back end for us. And on the front end for them. We also have automated money movement tools that if they use our tools, it eliminates so many of these back and forth error adjustments that for us create a delivery problem post-sale for the, for the supporting the customer that create a bad margin profile or a negative margin profile. We can help influence that by creating a better experience at point of implementation with them.

Right.

These are things I promise you we were not thinking about 5 years ago. It was like, customer acquisition at all costs. Right. And now as the business has evolved through the data and the analytics, we're able to create a better experience and a more efficient experience.

Yeah, I recorded a webinar with the CRO of ZoomInfo and the president of Sion, and this was one of the topics is like, how, how quickly can you get people to orient to post-sale in, in a startup's journey? Because everybody says they do it too late. This was one of my This was one of the big lessons of my first VP sales role, was just the importance of nailing that. Because it's not until you own it that I think you viscerally feel the pain of sales reps being sloppy with their handoff or expectation setting or onboarding being under-resourced, and then you quickly rally around it.

Yeah. And we're finding that to be even more true on the private equity side. We knew it, but it's accentuated on that side because what will happen is if we don't create a great experience at point of implementation for a portfolio company of X firm, that becomes the reputation of Carta across that entire firm, which means our ability to go win any of the other, you know, portco number 2 to portco number 99, we diminish our opportunity to be able to win those if that's the reputation of Carta inside that firm.

Yeah. And so do you have a full-blown, like, professional services team there, or is it more CS? Like, how does that look?

Yeah, not professional services in sort of the way I would think of it. Like, at Oracle, you could— we would sell, like, Oracle Consulting as a package. We don't. We provide that as part of our subscription. But we've built out what we call delivery teams that support each of those 3 businesses. And those are very distinct. Linked delivery teams because what supporting those different companies or firms means is different at Carta.

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I guess this means the profile of leader you have to hire is different than normal. Is that, is that fair to say?

It is, especially as the business has evolved. When I, when I joined Carta, I inherited a few frontline managers. That were, they were great, like building the cap table business. They were the classic, like, had been a really good AE and now become a manager and sort of career progress. That has changed as the businesses have changed. And so we still have that model. If you think of like the SMB type sales structure with a frontline manager, I would say on the venture capital side, we've started to supplement with external talent and people that come with industry experience and client relationships. Um, and so it's just a, a different profile of like what the organization will look like as we move forward.

Yeah, because I, I would imagine that because you've got all of these nodes that have to be broken down within the, these business units, the manager probably needs to be more strategic, more, uh, project-oriented than typical because, because you'll have like a VP for each business unit's sales org or how does that— maybe let's transition into the org design conversation now. Okay. And just like talk me through how the org is designed and I'm going to come back to the type of leader.

Yeah. So yeah, on the org design, I have a leader for each one, whether it's director, senior director, vice president. They're at different stages, but there's a lead, call it a leader for each of those, the businesses. Corporations is, you know, pick your, your SaaS startup. It's run just like that. There's an SMB team, a mid-market team, an enterprise team, which for us enterprise is late-stage private. So, you know, think unicorn or companies that are on their IPO path. And so we're structured that way. And then we have what we call a growth team that if you don't sell, call it all 3 products on the initial sale to the customer, which you don't typically, we have a team that, does the renewals and the, the cross-sell, upsell of the additional products there. Um, and so there's a, you know, your classic, like, uh, teams of, call it, you know, 6 to 9 AEs with a frontline manager that all roll up to, to the leader of that business. That's very different than the venture capital business, which is, uh, a VP that leads a business with, um, there's a couple of what we call enterprise reps in that space. And then we have teams segmented for first-time fund and then what we call established, which is obviously a fund that is, you know, past fund one and established and adding additional funds. And they now are responsible for selling the additional products too. And then we have, we have a, we have what we call a growth team there as well. So when they're raising a new fund, Um, that growth team's responsible for, for that and also educating on new products, like I mentioned, Tax and Tactic as, uh, as additional products to sell. Very different structure than private equity. Um, that one is split into, um, uh, portcos and firms by team. And so there's a portco team that looks and feels and operates much like the corporation's business, uh, but they're, uh, private equity portcos. and they are territory aligned with a firm AE that has responsibility for the firm that owns those portcos. Doesn't exactly match like every firm to every portco because there's some— I'll spare you the, the dirty laundry of that. But in general, the, the, the, the thesis is like you get a firm AE working with a portco AE to do that tops-down, bottoms-up approach to win. The firm and all their portfolio companies.

Yeah, it makes a lot of sense. Um, and the firm AE is probably like the enterprise type, like much more seasoned.

Exactly. Yeah.

Okay. And do people graduate from team to team? Like, do you graduate at a corp to funder to PE, or is— what's the, what's the path?

They do. It's, it's one of the— my favorite things about my career path is getting to see people come in as an SDR and grow and develop and move into you know, an SMB AE and then a mid-market AE. I would say one of the things unique about Carta is, um, we have what we call mountain jumping, uh, which means you don't necessarily have to just because you came in as a corp SDR, your only path is to stay in the, the corporation's business. Um, if at any given point, like you have a desire to, to try and work in the private equity business or in the venture capital business, we allow those opportunities. You know, it's obviously like time-based and business needs based on what the open headcounts are. But what we've found is having people that have Carta experience, they obviously ramp into whatever mountain they jump to much quicker than someone would from an external perspective.

And are you looking for a different profile of rep to, to mountain jump? Like, do they need to be more enterprising and scrappy or?

We are, which is why the mountain jumping doesn't always work for everyone because some people just don't have those specific skills. But yeah, I mean, what we, what we've learned and what we're building to is a much more experienced sales organization or people that come even from the outside with specific experience, either in accounting, fund accounting, have worked at a competitor and really know how to sell fund administration. Um, that's different than someone that like grew up and learned how to sell, uh, you know, much smaller ACV cap table deals. Uh, and so the profile that, you know, I'm working on with the leadership team and our recruiting team is very different when you're looking for those enterprise hires.

Yeah, makes a lot of sense. And so in corp and the funder business, you have reps and growth reps who sell add-on products. And in PE, it's, uh, Portco and Firm, and they're selling all products.

That's correct. We don't have— because it's a, a newer business, uh, we don't have as much of the, the upsell cross-sell yet for that business. So I don't have a growth team there. We may at some point. Um, we'll monitor that as the, the business continues to grow.

And how did you decide to have growth reps separate from the new business rep as opposed to having the new business rep own that relationship, try to land those additional products? Like, what was the, what was the whole evaluation like?

Yeah, it's such a good question. And I don't know that we ever have it right or not. But, you know, we've, we've, we've had the debates for hours here. And there's actually one caveat. There is one part of the venture capital business where I do have that in the enterprise space. The AE holds and maintains that relationship in perpetuity, call it, where they sell the first fund, they keep that account with them. And that's because there's only a finite number of funds in that space and not growing that fast. So allowing them to sort of keep and maintain a territory and the importance of establishing and building the relationship with that CFO or the, the office of finance in that firm is really important. The other ones we felt like creating specialization around the velocity of the business, like incorporations, understanding how to value proposition the total compensation product and the tax advisory products, getting that off the plate of the new business AE and allowing them to— the hunter-farmer analogy, allowing them to hunt, we felt like was a better model for that business.

Yeah, makes, makes sense. And what, what data did you have to look at to make that call? Like, can you— was there much or is that more subjective?

A little of both. But, you know, we're constantly looking at like, you know, conversion from lead to opportunity and conversion from opportunity to, to close one win or deal. And so, you know, doing the analytics of that doing the analytics of, number of, take the corporation's business, what we call a trifecta deal. If you're able to sell the cap table deal and total comp and tax advisory in the first sale, like how many of those were we able to do versus are you, is your responsibility to sell the cap table deal and plant the seed through the discovery with that customer that Carta has more to offer than just cap table. And so you're doing the first point of education. To be able to tee that up for the relationship or the growth AE down the road to be able to come back and have an opportunity to cross-sell. So we look at all of that data, like percentage of attached deals, we call them, where there's multi-products and like what's working, what's not working in each of those spaces.

Yeah, because sometimes trying to sell those extra products upfront can actually slow the deal down, lead to just like overload, information overload, and get your deal stuck? Yeah.

So one of the things I think we're really good at is, is sort of being patient with that. I'm less concerned about it slowing the deal down. In fact, the AEs actually care more about that than me. If it slows it down, I'm kind of okay with it because overall, like, it sort of washes out for me. I fear that trying to force a trifecta deal or a multiproduct deal just creates a worse customer or prospect experience. And that's more important to me at the time. Like, I feel like we will, we will win the other two deals later. Let's create the best possible customer experience at first point of interaction with us. And that's more important to me.

Right. So your attach rate must be pretty good then for the other products.

It is pretty good. Yeah. We were over 50% in, call it Q4. Uh, yeah, end of last year. So, which is actually really impressive. If you think, you know, half of the deals that come to us, they think, um, my lawyer sent to me, or I worked at Carta before, I know about the cap table, or I worked for a company that used Carta before, I know about the cap table. I'm going to come to that AE, and then we talk to them about additional things that we can do for them. Uh, we have a pretty good attach rate.

Okay. That, that makes a lot of sense. So what teams are distinct within these business units and how do you think about stitching it all together? Like, what are the, what are the input decisions that lead you to say, you know, should we have solutions engineers tucked under the same VP, or do they all roll into one VP of SE, but then they're dedicated by, by business unit? Like, what's your rationale there?

Yeah, I think, um, so that's a great example where I'm not sure there's a right answer. There's a choice we've made, which was to keep it, uh, distinct. Um, and frankly, it's because it didn't exist before. And so I had someone that had been at Carta for many years, who just sort of was a catch-all, knew everything, and like the person that people would go to when they were stuck on a deal. And so he seemed to be the right person to kind of build this around. And so we started with a couple engineers for the cap table business and primarily to help with our, the compensation product. And then it became, okay, now we need like specific engineers to help with the, the fund administration business. because it's a totally different discovery process. You're scoping the funds. Uh, there's just so much more that goes into that component of it. We needed to build a team around that, and I felt like having the sales leader have that tucked under them would distract them from the things I needed them to be prioritizing on. So let's build around this, like creating this team of like, uh, engineer bank for us to all be able to pull from. And so originally when that team was, was founded, you know, it was a team of 1. It became now a team of almost 8 or will be 8. And they were, they were product specialists themselves. And so if you were, you were the engineer for Corp or you were the engineer for Fund Admin, and now what we're doing is cross-educating them all so that they all can be that much more versatile and move and help in any of the businesses. And so many of the questions that people get are so tied anyway that you have to be you know, a bit more like chameleon and be able to answer a little bit of a fit into any situation and answer any type of question. And it just gives us a deeper bench for wherever we're going next to the more people that know all 3 of the products or all 3 of the companies here, the better off they're going to be. So in fact, I was talking with our— my leader of the corp business yesterday, and he's starting to implement a certification process for his corporations or the cap table AEs learning and understanding venture capital and private equity too. That's going to help them with the mountain jumping at some point in their careers, you know, hopefully 18 months, 2 years down the road, whatever it is. Uh, but getting people to understand all the businesses so we have that much more versatility at Carta.

Yeah, makes sense. So your belief is that the SEs can learn all 3 business units. And be effective, but on the AE side, the specialization makes more sense. Is that because the AEs will progress faster through roles? Like they're, they're not going to stay in seat as long? Or like, what?

Yeah, I think it's a combination. There's some of that where it's like you're going to be— you're going to progress through a role faster. You also, you know, the sales role is very different than the sales engineer role. And so like, do you want to be the hunter? And go prospect, or do you like being the person that gets to come in to the teed up opportunity and you get to demo the product that we think adds a ton of value? And those are very different personas.

But you have— you're generalizing SE, but you'll keep reps specialized. What's the, what's the mental model for that decision?

So I would say we're— I don't think we'll ever go to generalizing, but I want them to be more well-rounded.

Okay.

To be able to speak to anything. Yeah, there'll always be specialization inside of that team. There has to be, but they need to become much more well-rounded. And some of it too is, you know, becomes like key man challenges as well, right? If all of a sudden like someone that, you know, we have a couple examples of people that have been at Carta for 9 years and it's like if they decide like this has been a great run and I'm going to go do something different, which happens, I need to have a bench ready of people that like are ready to support all the businesses.

Right. Makes sense.

Yeah.

So what's your mental model for making all these decisions? So somebody say I come to you and I'm like, hey, I'm thinking about reorganizing my whole team. How would you walk me through trying to make that decision?

Yeah, I would say like, you know, I don't know that I'm right for doing this, but I look for consensus in decisions. That can also cause issues. I'm aware, like, more opinions means you have trouble getting to consensus, right? But I like gathering information and thoughts from a bunch of different parts of the business. And I have people that I trust that have been in these businesses for for several years. And so that's how I kind of think through it. And then I always sort of reverse the question to people. And this is something I've learned from Henry. I think he's a master at this of like, you go to him with a problem or, you know, something that you kind of want to brainstorm. And the first thing is like, well, what are you trying to achieve? What are you trying to— what's the outcome you're looking for based off of this decision that you're asking a question about or a reorg or whatever it might be? And so if you can kind of start there of like, what, what you're trying to get to with the future state and what problem that solves, then you can kind of troubleshoot it with the consensus of, are we making the right decision? We typically at Carta, like, I can't, I can't think of a sort of an important decision that we've made over the last couple years where we haven't had at least 2, if not 3 or 4 options on the table. And typically what ends up happening there is, I can visualize the, the slide in my head now where there's 4 options. And typically we end up like with a 5th option, which is something that is sort of a combination of a few of the ideas that have come together, because having the conversation, having the discussion allows you to get to a place where you've made what you collectively think is the best decision to move forward with.

Okay. And so what would you say to somebody thinking through it like this is the— these are the key inputs? You know, like you need to look at this data or you're optimizing for this customer outcome. Like, how do you think about the inputs to that whole framework of like org design?

It's such a timely question because this is what Henry and I talk a lot about these days is like he cares about the outputs, but he'll, he'll say he doesn't care about the outputs. It's the inputs. That are most important. So what are the things that we are doing within our control that will get us what we think the desired output is? And he says this to me all the time. He's like, you know, the number will be what the number is. Like, are we doing the right things with the inputs on a daily basis? And so I've tried to instill the same mentality with our teams as we think about any of the decisions we're making is what are the things that we can and should be doing that help influence better top of funnel to better conversion rate to better close rate. And it really, if all everything boils down to those couple of things, the output will be like, we will get the good result. I'm confident in that if we're doing the right inputs. And frankly, I didn't think that way when I was at Oracle at the time. I just thought like, you better hustle and you better prospect and you didn't know any better, right? And so now, like, as you sort of mature into the businesses and you have more experience, you think about like, like, how do you influence this? How do you work with, uh, the product team to provide feedback on, like, either what customers are saying that they want improvements on or things that we're hearing in the market that allow us to compete in a better way? How do I involve, uh, Nicole and my, and my marketing counterparts to be very targeted and specific in some areas or more general and brand awareness in others? And so it's a, it's a combination of sort of pulling all those things together as the inputs that get us the output. It.

Yeah, makes a ton of sense. One of the things that I stress to my teams is this sort of decision-making hierarchy. It's customer, company, team, rep, manager last. And, and really trying to force people to think about, okay, if you're thinking about org design, well, like, what is the org design that best serves the customer, that makes their experience the easiest, the best? And, and typically that will result result in the best business outcome. But this, like, hierarchy is a thing that I feel like sometimes is difficult because you disappear into a spreadsheet and you're like, okay, well, if we do this, then the outcomes will be X and conversion rates will be Y.

But that— and I think, you know, I agree with you. And I think the hardest thing about that is sometimes that end decision doesn't always maybe feel the best for, like, people on the team specifically. And so that's the balance of, like, the hard part of the job is, like, not everyone's going to love every decision, but if you feel like you've done the diligence on making the decision that's right for the business and the customer, then the rest of it is like how you get the team on board with the decision and either include them in the process, uh, or be very clear and crisp on explaining the why the decision was made. And I've found in just about every case, if you can explain and articulate the why behind things and get people feeling like they're part of the decision, getting them on board with the rest of the process is very easy.

Yeah, we're, we're trying to do that a bunch right now. The, It's always hard to find that balance between being really open with your communication and sharing a ton without just overwhelming people because then they turn off. And so we got feedback in our last enablement survey that people were frustrated with reps breaking the rules of engagement. It's like, hey, you guys aren't enforcing the ROE, so people are taking advantage. And we went, it's like, man, we spent so much time on the, on like these ROE decisions and we're like going through ops. We close like hundreds of deals a month, like 400 or 500 deals a month. And so there's like a lot of ops to comb through. And I'm like, I feel like my manager spends all this time on it, but the reps feel like we're not paying attention. And what was missing was we weren't, we weren't sharing the the rationale behind the decision-making publicly enough. And so one of the changes we've made is when— so the managers take a, you know, they take a situation into the manager channel, they're going to debate and they're going to look at the ROE and make the decision. And then we're trying to publish basically that entire argument, like a synthesized version of, hey, we looked at this, we looked at this, we looked at this. Therefore, this rep based on the ROE is going to like get credit. This one's going to lose. We had one where the manager made the mistake. And so the manager in the thread was like, hey, actually, like, the BDR shouldn't have done that, but I told her to because I, like, misinterpreted the ROE. So, like, they should both get credit and, like, I should lose it. And then we published that whole thread to the team, and hopefully that will get better because we spend so much goddamn time on these ROE disputes. To have somebody be like, you're not paying attention, I was like, oh, That's brutal.

This is great therapy. Thank you. I'm glad I'm not the only one that deals with ROE issues. So good to hear. Yeah. You know, I mean, the complexity of Carta, like, we obviously have ROE issues. You and I haven't even talked about our international businesses yet today, but yeah, obviously, you know, when you start to bring in international teams, like, ROEs come into play as well. And I think, like, you know, early days, I actually had a lot more problems with that because, Early days was Wild West. It was like inbound lead flow. Everyone do demos as fast as you can and bring customer acquisition. Once you start to put some structure in place or some segmentation between SMB and mid-market and enterprise, or you start to have other business units, ROEs are going to be a challenge.

Yeah.

And then I actually think the, you know, the building out of the sales ops function, at least for us, was always behind. And so So when you don't have that like fully built out, it makes the ROEs even more difficult to track and enforce. Now I feel like we've caught that up and we have, we have a great sales ops team here now. But, you know, early days it was like a team of 1 or 2 trying to, you know, keep all the, the, the org together with some duct tape and bubble gum.

Yeah. So is that, is your, is your ROE the domain of sales ops? Are they making those decisions and tracking and enforcing?

Um, they're not, uh, the, the, they, they, they track. Um, I don't expect them to enforce because what I want is them, like each of the leaders of the organizations to like figure out if there was, call it an infraction of an ROE or like where the actual lead or deal should go. Uh, and then if they can't, um, figure that out, like I arbitrate in the end with sales ops.

Yeah.

Yeah. And frankly, like, that's arbitrated. I'm surprised it's even coming up here today because I feel like it used to be a thing and, you know, we put the right measures and you brought up a great point, like we're clear and transparent on what the rules are. So it takes all the gray out of it. As I say that, there's always some edge case that comes up and something happens. But for the most part, this has become less and less of an issue.

Okay. So how— it's funny, I can't believe I'm talking about ROE on one of these, on one of these interviews. So how robust is that process for you? Like, is this a monster doc or is it just like a simple framework?

Yeah, it's not a monster doc. It's a simple framework with one Slack channel where if something gets escalated to me and I'm more of a talker, show me. So like, don't send me the whole thing in Slack and both, both sides of their positions on why it should be where I'm like, yeah, let's get in a room for 15 minutes and talk through this and let's do like common sense, like what, what's right for the business and who supports this customer and where does this deal go? Uh, and then if there's an adjustment to be made from, uh, an attainment standpoint or a compensation standpoint, like let's talk through that. And we've always done right by our AEs here. So, uh, it really, uh, it was, is, is not much of a, a big issue for us.

Okay. Interesting. Yeah.

Um, I used to, my days at DocuSign, at Oracle, I mean, you're, you're battling like, is this an enterprise account or a commercial account? Or when I was at DocuSign, it was like, is it, you know, SMB mid-market or is it majors? And you actually like end up bickering with people that are like your friends and your peers because everyone is like just trying to win, you know, and trying to win and trying to stand up for their teams in those cases.

Yeah, it's funny. I find the reps who are friends bicker the most because they have enough relationship to be like, no, no, no, kick rocks.

This is me. This is mine. Yeah, yeah, yeah.

Yeah, we're still working through what that needs to look like. I feel like that document's too big now, but when it was a little looser and it was more, hey, just make the right decision, it was too opaque. And then people were frustrated. They're like, well, this person's getting this. And the accusations of favoritism when people are always going to see the world through the lens that is the most kind to themselves. And so, logic didn't really hold that strongly there. So, we're trying to codify basically everything and say, "If it's outside of these guardrails, then it's just going to go the other way. There's no room for interpretation, black or white." We'll see how that goes.

We're pretty much centric in San Francisco and New York right now, but at one point, we had some other office locations. And I'd even have situations where folks in some offices felt like they were getting less leads than others. And because it was ROEs and like, I didn't care. I wanted everyone to get the exact same amount of leads and like, let's figure out who converts best and who wins. And, uh, but yeah, these to me, just like put them in like the backpack of experiences of building businesses as they scale along the way. Yeah.

Yeah. That makes sense. And so where does international tuck into this whole thing?

Yeah. So I've, I had responsibility for the international sales teams about a year ago, and then we made a decision at the exec team level to, to hire basically a GM model for those businesses to have them focus on that, which actually it's better. As much as I'd like to stay connected to those businesses and try and help them as much as possible because they're important for the future of Carta, reality is having a GM in, in continents in it is much more helpful at this point. And so we hired a GM in London to manage our Europe business, and then we have one in Singapore that manages our Southeast Asia business too. Yeah, because, you know, I try— like, there's— to me, there's gray area in everything. I just, you know, I just hosted our sales kickoff in early January, and I included those teams as part of it as well, because I think it's important that they're taking in everything that we're putting out as far as strategy and direction for the, for the company for, for the upcoming year, they need to be a part of that too. So, and it's great, like, it's amazing. I give some stage time to each of those GMs, and those are two of the most popular sessions because our people in the US want to hear about what's actually happening globally because they just don't see it every day. And it's a great opportunity for our global leaders to share about what what their actual teams are doing and working on.

Yeah, that makes sense. And those businesses can be just so different. I've had, I've had different international teams over the years, and it is shocking how different businesses run in Hong Kong versus France versus Germany.

Even just in Europe, they operate differently alone, right? So yeah, it's definitely challenging, which is why having someone there is really important.

Yeah, that makes sense. And, and, you know, those businesses, I, I would imagine, are such a completely different stage of maturity that it's— it'd be hard to get enough of your attention to, uh, compared to a GM.

That's right. And, you know, um, we want them to feel supported but also not be a distraction for our US teams. Like, if you're going to go focus on things that are happening in London, you're missing something that's task at hand that like maybe has a larger TAM for you in the moment.

Yeah, makes sense. I think I got through the important org design stuff. So let's jump into quickfire. What do you think separates a good CRO from a great one?

I think it's balance. And that's balance sort of across the board. It's being able to like sort of step back and not just be like everything about the people, but about the business and the strategy and the future and the org design, making the tougher decisions, maybe not the most popular decisions at times, but like having the sort of the authority to be able to do that and the command of the business to be able to do that. While also being like very relatable and close to the people that are part of the business. I think that's really important. And, you know, you observe how people operate in different ways, and I'm not sure there's a right or a wrong way. There's just different styles. I've always tried to balance the two, and I don't know that I'm good or great at it, but it's me and how I operate. And I feel like I try and do— I was sending prospecting emails for an SMB AE this morning before this call because I was talking to them in the kitchen and said, I can't get this person to call me back or email me back. I said, well, let me give it a shot. And so I'm not above doing that. I'll do it. Like, we're in this together, right? And so you kind of want to be sort of with the people and helping and supporting them. But then you also have moments where there's sort of this separation and you're making decisions. It can be headcount decisions, it can be reduction of team sizes, it could be shifting resources to different directions that might be unpleasant for people. So you got to figure out that right balance of how to, like, lead lead, but also, you know, hold accountability across the organization.

Yeah, that's cool. I read this Brad Stahlberg book last year called Master of Change, and in it he talks a lot about non-dual thinking.

Yeah.

And it's a concept that I had only like roughly been familiar with, and then it caught my attention. And so I read the stuff in the book and then some things after, and it's one of those things that now that I know about this concept, I see it everywhere. I just see this pattern of being able to be having an extreme sense of urgency in everything that you do and also an extreme patience with things. And, you're talking about this non-dual approach of being able to be relatable and there with people and have that relationship and then be totally disconnected and be able to make an objective decision. It's a fascinating pattern that now is just everywhere in the world. That I look around.

Yeah, I've jotted that one down. I always get good recommendations. So, uh, thank you. But yeah, that whole notion of like, I mean, I, I've been pushing with the team now, like everyone needs to be operating with urgency because I feel like we have this window of time to capitalize on where Carta is in the market in each of these businesses to really build a great generational company. And I don't want any moment wasted for us, um, across any of the teams where we have the ability to go do that.

That. Yeah, makes a ton of sense. Yeah. Master of Change is an awesome book just in general.

I wrote it down. Thank you.

Yeah. So many cool learnings. What's the most common advice you find yourself giving your leaders?

Common advice. I think as I talk to sort of like earlier stage in their career leaders or even the folks that report directly to me, it's I'm like, um, like, what do you do when no one's watching? And how do you operate when no one's watching? Uh, and then I say to them, because you know what, someone is always up, is always watching actually, right? Um, and, and to me that's important. And I think I learned these lessons back in the, in my days at Oracle where you just try, like, I had bosses that were remote at the time, but I wanted them to feel like they could, they trusted me to lead my teams and manage my business accordingly. To where I was a, a positive reflection of them and their leadership in the business. And they could trust that I'm doing all the right things on a daily basis, even though they weren't sitting in an office right next to mine at the time. And so I've just sort of taken that to heart and each step of the way career-wise to try and be that person. I don't want Henry to think like, do I have to wonder what Jeff is doing today? Or do I trust that he's leading the team and leading the business in the right way? And then the reverse on that of like, because someone is always watching, I've found I've benefited from career opportunities as a result of that because I know that people were always sort of watching and observing who leads their teams in an appropriate way. And those are the people that got the next opportunities. And I got to benefit from that career-wise along the way. And so if, you know, if you can be the person that's like leading by example and doing all the right things when no one's watching, the person that's actually watching will be the person that helps them with their next step in their career path.

Yeah. And, and executing like a professional and, and operating in this manner doesn't guarantee success because, you know, luck plays a big role in the world, but not executing that way almost, almost solely guarantees failure.

I totally agree with that. Yeah. You have to do everything you can possibly do to position yourself, put yourself in a position to be successful. But if you're not doing all the right things, then you have no chance. And that, that's clear and obvious.

Yeah. Yeah, for sure. It's, uh, classic Jim Collins return on luck, which, which I always like. Um, what's the hardest lesson you've had to learn in your career?

Um, I think a couple things. Uh, I would say, you know, most people I think struggle with what I call like career patience. There's no one out there that like doesn't want like more money or a bigger, bigger title or more responsibility. Although there are that don't want that. I get that, at least the more responsibility. But in general, like most people are driven and they want the next thing or they're expecting the next thing. And the reality is like if everyone is promoted once a year, is everyone going to be CEO within like the next 6 years? It just doesn't happen. And so I think, you know, one of the things, again, a great lesson learned from my time at Oracle was this, this sort of patience because like the next step wasn't always right there in the next year. And I spent multiple times, like 2, 3 years in a role, and then the next responsibility opened up, and I was like doing all the right things on a daily basis while no one was watching to be best prepared for that next opportunity. And so I think that's like the biggest thing is like be ready for the next thing, but you got to be patient along the way. And actually, every time I thought like I should be promoted faster or I should have this job, when I was— it took me an extra 2 quarters, and then that role opened up, actually, when I reflected on it, I'm like, I'm actually that much better prepared for it, given the little extra time I had in seat and the different experiences I had along the way. Yeah, I think that's one. The other is like, um, I think over time, like, the increasingly, um, importance of, um, proper performance management across the teams. Uh, you know, what you find is like, if you're not doing that, you're doing a disservice to, um, the person themselves. Themselves and maybe where they should or shouldn't be in the company. But you're also not just helping your own team and that person be as productive as they possibly can. And that leads to all kinds of issues down the road. You have poor performance, you have team culture issues, and inevitably HR issues, legal issues, all these things that come up as a result of not identifying a problem early and working to remove that problem.

Yeah. And it really depends on how you do performance management. We don't call them PIPs, we call them coaching plans here. And the thing I emphasize to my managers all the time is a PIP is not paperwork to terminate somebody because that's always the attitude. I tell people to go into a PIP, I'm like, your job is to fight like hell to help this rep beat the PIP. And, it should be a tool that is really productive. And, I have a bunch of reps on my team who are tippy-top performers now who were at some point put on PIPs because stuff was going on, they needed a little kick in the pants or they just went through a rough patch and needed to have a reminder of the expectations and it gets their mindset queued into the right place, and then you give them that momentum and they never look back. I've got multiple top performers who are on PIPS, which is so fun.

I have— I'm thinking of a couple of great examples here too that have built wonderful careers now and are amazing leaders that had, you know, maybe a little bumpier start along the way, and that's okay. So yeah, I mean, I think the other, the other flip side to that is oftentimes you either one, you don't have support from an HR team that can kind of help you with this to engineer it in the way, in the spirit of like, how do we help the employee improve? And then the other is you get oftentimes like top performers that were never on a performance plan because they were top performers and then they become a manager. And how do we expect them to know how to actually like performance manage if like they never had to worry about that because they were always a top performer? So, yeah, there's an education process that has to go along with, with newer managers too.

Yeah. If somebody's listening and they are thinking, I wish I knew how to do this better, I, I want to do better PIPs, send me an email and I'll give you my coaching, coaching plan document. Um, all right, last question. What's the best thing that you've read in the last 12 months?

Uh, last 12 months, um, a couple things if that's all right. Um, we did, we read the medic book because we've, we've, we've been a Sandler company and now we've, um, uh, instituted medic as well to to help us better qualify opportunities and focus our time better. So I think that was really helpful for the teams. I had been exposed to it previously, but I think as far as like the rest of the organization, really helpful. Simultaneously, I read Impact Players by Liz Wiseman. I actually was gonna have the entire—

Such a good book.

Such a good book, yeah. I was gonna have the entire organization read it prior to kickoff, and instead I just asked the leaders to. I didn't know the whole thing would be completely applicable, but I found that to be really helpful in just thinking about like, you know, talk about wanting to be promoted or how do you separate yourself? Like, make yourself an impact player. Like, make someone say, what happens if this person is not here anymore? What gap is created? So that was good. I also read— I shared this with Henry a month or two back— a book called The Power Law, which is basically— yeah, I enjoy like history. So to me, this was like history of venture capital, which was really cool. It goes back to like, you know, venture capital starting in like the '60s and sort of how that progressed. Best. Um, uh, and they are growing up kind of in Oracle and seeing how all this investing happened. I found that really interesting. Yeah, I was given a book yesterday by a vendor, uh, who maybe I'm gonna actually buy their product because he was very thoughtful on this, uh, called Relentless. Uh, he knew I was a sports guy. Apparently this is, uh, this is the, the Maori, uh, rugby team. Uh, no, this is more Michael Jordan, I believe, because there's some Kobe Bryant stuff. Yeah. Uh, Relentless. Countless, uh, From Good to Great, it's called. It was Tim, Tim Grover, I think, was—

oh yeah, yeah, yeah.

So George's coach, George. Yeah, so, uh, I haven't gotten into that one, but it was gifted to me yesterday, so I can't wait to get started there.

Nice. If you liked Power Law, I just started reading, uh, Chip War, which is all about how the semiconductor is like the most important resource in the world and how it's the geopolitics of it. It's, it's a pretty good one because it's a blend of technology and geopolitics, history. It goes some of the early innings of Silicon Valley's emergence. It's cool. All right.

Chip War and Masters of Change. I wrote them both down. Thank you.

There you go. Well, this was awesome, Jeff. I knew this was going to be an interesting one. I feel like I'm walking away with this with a bunch of really cool mental models and perspectives here. So much appreciated. I'm also really struck by your humility. Like, you're, you're clearly like a very thoughtful, humble guy who I can see why people really enjoy working with. That, that's like a— that part of your leadership, that part of your leadership DNA, like, really jumps out. So appreciate the time. This was awesome.

Thank you. I appreciate that. I feel like, you know, what I share with the teams is, you know, whether how much time you spend either physically in the office, present at work, or just mentally thinking about work, for the amount of time we put in, we should actually like like enjoy the people we work with and help support each other. And I've taken that sort of principles in how I operate and have a lot of fun in who we work with and what we're trying to achieve at Carta.

So— Couldn't agree more.

I appreciate you having me.

Yeah. Where can people find you if they want to learn more from you?

Yeah, I'm on LinkedIn. I do a little bit of Twitter, but not as much, or X, not as much. You can tell. But yeah, just hit me on LinkedIn. I get messages every day. Or you can email me, jeff.perry@carta.com. and we'll definitely respond. I'd love to hear from, from your audience.

Cool. All right. Much appreciated. 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.