GTM 141: Timeless Growth Tips From a $7.4B Oracle Exit and Scaling Carta to $450M in Revenue | Jeff Perry
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Jeff Perry is a truly iconic revenue leader and the Chief Revenue Officer (CRO) at Carta, responsible for core software revenue across New Business, Upsell, Cross Sell, and Customer Success. Prior to Carta, Jeff led SMB Sales at DocuSign, and started his career at Oracle, where he rose from Strategic Account Manager to VP of Sales over a decade.
Discussed in this Episode:
How to turn coworkers into mentors—and why it matters.
Moving from enterprise sales leadership to a startup environment.
Why and when to build a solutions engineering team.
The myth of the “18-month CRO lifespan.”
Balancing empathy and accountability as a sales leader.
Why automation isn’t always the best path forward.
If you missed GTM 140, check it out here: How Microsoft Scaled from $600M to $5B: The Enterprise Playbook with Hayden Stafford
Highlights:
06:29 — Mentorship matters. Jeff breaks down how to find and approach mentors—even without a formal program.
12:42 — Lessons from selling servers that still apply to modern SaaS sales
15:02 — Leading through M&A: Inside the culture clash and how Jeff rebuilt a team post-acquisition.
28:34 — Scaling revenue from $20M to $450M: Advice for CROs entering growth-stage companies.
33:20 — Why “big company” people can thrive in startups—if they leave their playbooks behind.
36:15 — How to use PIPs to coach—not just cut—and what most orgs get wrong.
43:13 — Why the best sellers are quarterbacks, not lone wolves.
46:43 — Pick up the phone: Human connection wins in an era of AI and automation.
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LinkedIn: Jeff Perry
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Host Links (Scott Barker):
LinkedIn: Scott Barker
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The GTM Podcast
The GTM Podcast is a weekly podcast hosted by Scott Barker, GTMfund Partner, featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
GTM 141 Episode Transcript
Jeff Perry: I love the building part. I love, like taking something from early or zero stages and seeing, the impact that you can make on it. you never know when the door’s gonna be open and you gotta be prepared to kick it down when given the shot.
Scott Barker: I won’t bury the lead, Jeff has grown revenue from $20 mil to $450 mil, pretty incredible run
Jeff Perry: I’ll admit this, like I was motivated by fear of failure. So I was like, I don’t wanna fail, so I’m gonna get as many smart people to help me not fail.
Performance management helps the organization be healthier and stronger.
You don’t have to be the hero. Be the quarterback of the deal.
One of the biggest things I learned in that process too is the importance of the solutions engineer organization.
I like to get input from people. You could argue sometimes too many people, but that’s because I want people to have a voice
Speaker: Behind the scenes. It was a small group of people that were doing everything. Welcome back to the GTM podcast. It’s your host, Scott Barker. I wanna know how this insane growth actually happened.
Scott Barker: Hello and welcome back to the GTM podcast. Thanks for hanging out with us for the next hour. Uh, as always, we like to bring you strategies, tactics, tips and stories, uh, about how the greatest software companies have been able to scale, and, uh, certainly have the perfect guest, to talk it through. I am joined by my man, Jeff Perry.
Jeff, what’s up? Welcome.
Jeff Perry: Scott, how are you? Thanks for having me. Good to see you again.
Scott Barker: Good to see you. Good to see you. And we’ve been, uh, trying to make this happen for a little bit. I got sick the first time we were gonna record, but we’re finally making it happen and, uh, you know, since. Many, many of our chats I’ve had of like, oh man, I wish I had a microphone and we could just record this now.
So I’m pumped, we’re finally doing it. So just quickly, so, um, Jeff Perry is, you know, an iconic, I would say, revenue leader. He has been the Chief Revenue Officer for. It’s been six and a half years now, which is crazy. I feel like I remember you joining, but it’s already been six and a half years.
Prior to that, I spent some time in leadership at DocuSign and then spent about a decade at Oracle, culminating as a VP of sales and did some really, really interesting stuff there, which is kind of where I wanna start the conversation. Um, you know. When you first started at Oracle, I would love to just go down memory lane a little bit.
What did sales look like, you know, in the early days of Oracle, like when you were starting out. Now we’ve got all these fancy tools and AI and everything, but what was it like back then when you were first starting your career?
Jeff Perry: Yeah, well, obviously very different and, um, you know, learned a ton. Uh, at that time I actually started, uh, my, my sales career in the marketing department of Oracle, and I was selling, uh, booth space and sponsorships for the flagship. A marketing event called Open World, which most people think of as Dreamforce.
Now, a lot of the folks that were at Oracle, uh, left and go, went to build that conference, but I was selling, um, booth space, uh, you know, $41 a square foot and adding in, uh, talk about learning how to do upsell. You add in carpet padding, internet access, electricity for a couple hundred extra bucks. And that’s how I learned, um, selling at Oracle.
Reality is, um, I wasn’t selling like the actual Oracle products and over a period of time I had some friends in the product group, um, that actually encouraged me to, to move from the marketing team to, to the sales team. Uh, and then from there I just had an opportunity to like be part of the engine that Oracle had created, uh, and teaching people, uh, the fundamentals and the mechanics of selling.
Uh, and I didn’t realize it at the time, the valuable experience you’re gathering, but I had friends that came from around the country that moved to Redwood Shores, California just to get. Um, a couple years of Oracle on the resume to say they went through the training program and get the foundational skills to then be able to go on and do, uh, other things.
And so just a very different environment than we’re used to now, although it was very much set up like an inside sales organization is, which we, what we were. Um, and that allows you to bring in, you know, entry level, we called BDRs, but sort of our version of an SDR, uh, to come in and have the opportunity to learn and grow and develop.
And then get promoted into quota carrying roles, um, and, you know, have a support network around you of, of training, uh, and systems and tools. Um, and the most important thing I think is, uh, mentors that you have that had been at Oracle for many years and had been successful. And I think that’s where most of the, the learnings really came from is the knowledge transfer you get from, uh, more senior people that had gone through all the steps, uh, before I had.
Mentorship matters. Jeff breaks down how to find and approach mentors—even without a formal program.
Scott Barker: Totally. Yeah. Did Oracle have, I think mentorship is so important and we have a lot of, you know, younger folks that listen to this as well as, you know, leaders and founders. Did Oracle have like a set mentorship program or was it kind of still on you to go and, you know, build these relationships with leaders, you know, and, and respect?
And maybe if you have any advice on how to approach those. ’cause I think it’s incredibly important.
Jeff Perry: Yeah, it was, I would call it, uh, less formal of a mentorship program at the time. Um, so the onus became on the. The more junior employees sort of seek out the people that, um, you identify as top performers or people that you wanted to learn from and emulate. And I think that comes sort of in two paths.
It was from the individual contributor standpoint, so the sort of superstar field rep ae that were closing the multimillion dollar deals and then there were like. Those that were in the manager track, uh, and people that you wanted to, to be like or take a career path like them. so it became on the employee, uh, at that time or myself at that time to decide.
What sort of path? What do I like doing? What do I think I’m good at? What do, what, where do I think I can make the biggest impact? And then find the right people in the organization to help be mentors. And, you know, like I found at, you know, Oracle DocuSign and Carta, um, we have, you know, really good people that genuinely want to be mentors and wanna help sort of.
Pay back, uh, what was paid forward to them at some point and people helping them. And, uh, I feel like, uh, I’m very lucky and proud that I’ve gotten to do that over the years, um, because I had great people help me and give me an opportunity to, uh, maybe take on a role that I wasn’t totally ready for at the time, but they saw something in me or believed in me that gave me the chance to, to open that door, and that was the door for me to then go kick down to take advantage of that next great opportunity.
And. Of the great things I get to do now is open those doors for people that, uh, hopefully will, will kick them down as well and take advantage of those opportunities and go on to do great things,
Scott Barker: Yeah, that’s the beautiful part of, you know, being at where you’re at in your career is it kind of starts coming full circle and you’re able to, you know, pass on the opportunities that were once afforded to you. So you’re kind of now, you know, seen as this, you know, startup guy. You know, you joined DocuSign when it was very much a startup.
You joined Carta when it was very much a startup. Jury’s out if you could still categorize both of them as startups now. Uh, but they certainly were when you joined. And just for the listeners, I won’t bury the lead, uh, you know. Jeff has grown revenue from 20 mil a RR to 450 mil, so pretty, pretty incredible run for, for six and a half years.
But before you kind of. Jumped into the startup world. You were at Oracle and you know, we’ve talked about this really impactful moment, uh, which I believe it was 2010 if I’m getting the dates right. Oracle acquired Sun Microsystems. It was a huge acquisition at, might have been 2009. Um, huge acquisition, made a ton of buzz.
I think it was like 7.4 billion. You know, you don’t. See those type of acquisitions too much anymore. Um, but walk me through that, that time period. ’cause I know you kind of got the nod to help integrate that, uh, that company into Oracle.
Jeff Perry: Yeah, it, uh, it was, you know, pivotal time. Uh, Oracle had gone through hundreds of, of acquisitions, um, some small, um, some large, and, and the, the sun wasn’t, was particularly large, but, uh, for me it was a, a large opportunity to sort of change the, the career path for myself and, uh, opened a door for the new opportunity.
Um, and yeah, it was different. Like we didn’t know what we were doing as far as selling hardware inside of. The Oracle software company at the time. Uh, and I was asked to go help sort of rebuild, um, a sales team that was inherited from Sun and sort of instilled the Oracle way upon that team. And I saw it as like my startup within a big company.
I moved to a, a different floor that was empty in the Oracle building and. Started hiring and recruiting and building an enablement program. Building a post-sale program. You know, the teaching, the, the, the team structure, the, the scaling, everything that goes into really building, you know, a, a new team.
And look, I. I had Oracle behind me, so it wasn’t gonna fail. It wasn’t like I was using my seed money to get that company going, but for my career at that point, I had not had an opportunity of being in like, true startup. And that was as close as I had gotten. And really it kind of gave me the taste for, okay, I love doing this.
I love the building part. I love, like taking something from. Early or zero stages and, and seeing, you know, the impact that you can make on it. Um, and that was actually the impetus for me, you know, eventually deciding to leave Oracle, uh, ironically because that great opportunity had, but it allowed me to think about where I can go somewhere and make a bigger impact?
And then you think about it, I. The career path from there. And, um, you know, most people didn’t want or didn’t want at that time to just hire someone that came only from this big company into your nimble startup world. Um, and I was given an opportunity by Lauren Al Hadif, who was the head of North America sales for DocuSign at the time, who again opened a door for me and gave me a chance to lead the SMB team at DocuSign.
And that was my sort of. First taste of leveraging the startup experience inside of Oracle, but at a startup. And yes, DocuSign was large at the time, but in comparison to 120,000 employees at Oracle, it felt very small to me. Um, and my team size was, you know, when I went from roughly 225 people to 20 people when I first joined DocuSign.
And that just kind of gave you the taste of like the itch of the entrepreneurship of it, the building, something. Uh, and then, you know, four years later from DocuSign and I had kind of the same itch of like, can I do this even somewhere earlier? Uh, and make an even bigger impact? And then Carta found me and I found Carta and had an opportunity to do that from the early stages of where Carta was at that point too.
But I, it all back to like that moment in, you know, 2009, 10, where there was this. I never could have imagined there was this hardware opportunity inside of Oracle and I was asked to help be a part of it. Um, and that launched me into an entire different, um, career trajectory from there. So you never know when the, when the door’s gonna be open and you gotta be prepared to, to kick it down when given the shot.
Lessons from selling servers that still apply to modern SaaS sales
Scott Barker: For sure, and my understanding is it was kind of quite outside your expertise. Like you weren’t a hardware guy and you’re like, you just had the confidence. You’re like, all right, well I’ll figure it out.
Jeff Perry: The biggest thing I remember all of us were trying to figure out is like revenue recognition, right? And, um, as, as we know it in the SaaS world, like you sign a contract and recognizable revenue based off the quarter in which the contract is signed, I. When we inherited a hardware team, you actually don’t get to recognize that revenue, revenue until the actual piece of hardware was received in a shipping dock at the company that you sent it to.
And so these were things that just were foreign to me, having been in a software only environment prior to that. Um, and you know, you can pick your example of how bus different businesses operate differently. That’s just one small one where this was something different and we had to learn how to basically do two forecasts.
There was a booking forecast and a. Hardware delivered forecasts that we had to roll up, um, each month and quarter.
Scott Barker: Interesting. So when you, you could sign a hardware deal, but it wouldn’t go against your number for that quarter until it was delivered. Is that what I’m hearing?
Jeff Perry: Correct, but it would depend on which piece of hardware it was, because some could ship faster and arrive faster than others. So, you know, we focused on the controllable, like how much can you book? And so that was the pure focus. But then as far as with finance and, and recognizing the revenue, you had to monitor which of them.
The pieces of hardware actually had to be delivered. Were they sunfire machines or big hardware Exadata machines? At the time, Oracle was building software inside of the hardware as one package.
Scott Barker: Yeah, that’s interesting. I imagine there’s a lot of, late nights, calling some delivery drivers, telling ’em to hurry the
Jeff Perry: Yeah. Where’s, where’s, Where’s, the u Ps guy? FedEx guy. Yeah, but it’s about lessons learned and how to apply forward. It actually happens in our fund administration business now too. Although you’re not delivering a piece of hardware, you know, we aren’t able to recognize revenue until capital is actually called from a fund.
So there’s oftentimes where, if you’re working with a new fund, you book a contract, for the preparation of that, um, that capital being called for that specific fund. That’s when you actually recognize the revenue. So ironically here we are, uh, you know, almost 15 years later and I’m sort of applying a different but similar type of skill that I had learned at that time.
Scott Barker: Yeah. I love that. What were some of the biggest challenges? I mean, I, I don’t know the scale of how many people came over from Sun, but you have this team of, you know, 225 folks. I imagine there was, you know, there’s quite often culture shocks, you know, they do things differently. Maybe they have a different archetype of seller.
What were some of the biggest challenges in that integration?
Leading through M&A: Inside the culture clash and how Jeff rebuilt a team post-acquisition.
Jeff Perry: Yeah, I think, you know, obviously learned, learned a bunch of different things along the way, but I think the, you know, the reality of sort of setting in is like the reason why Sun was acquired is because that they were struggling at the time and though as a result of that, they had lost, I. A large portion of their, their sales force had, uh, had left the company.
Uh, and so that left us like the opportunity, uh, and the challenge to pick up the pieces of like who remained with the team and then sort of rebuild it into a new model. And at that time, they didn’t come with basically. A more robust inside sales model. And so we took what we knew as best practices from, from big Oracle at the time, uh, and in and instilled that into how we, um, we did the, the, the transition, uh, and the integration of, of the two companies.
And so I used sort of the model that I had learned from my time in both the enterprise business and the commercial business and inside sales. Replicated that model into a hardware model. but you learn along the way, things like the forecasting and the delivery of hardware and uh, you know, how do you, how do you train?
You know, you’re right. I did recruit some folks from my software teams at Oracle and you had to teach them like. The hardware component of the business and like the cores and the, the bits and fits of, uh, you, you know, each of the pieces of hardware that you are actually having to, to sell to customers, and be able to articulate the value proposition.
So I think one of the biggest things I learned in that process too is the importance of, uh, the solutions engineer or sales consulting, uh, organization. Because it wouldn’t have been possible to teach a bunch of folks that were earlier in their career and didn’t have experience with hardware at that time, frankly, didn’t even have a lot of software experience, but now you’re trying to teach ’em two different things, and so having people that had that institutional knowledge about I.
Hardware products and being able to, uh, help them, uh, through sales calls, I think was like a lesson learned. Number one is we need to be able to have an organization like that to, to support. And again, like you think about the fast forward, here we are 15 years later and we didn’t have a solutions engineering team, uh, at Carta until about two years ago.
Uh, and so using some of the same principles that I learned at the time to be able to say. Here’s a need we have in parts of our business. We need to, you know, exercise and develop that muscle of having that part of the organization to help support all of our sellers.
Scott Barker: Yeah. Yeah. If you could go back and, and do it again, would you stand up that team even earlier? or do you think that you have to get to a certain scale or a certain product maturity for it to make sense to make the investment in a solutions engineering team?
Jeff Perry: It’s a good question that I’ve actually thought, fair amount about. possibly, but I don’t think it was a necessity at the time. And when we were just the cap table company, uh, in the earlier days when I had started, I. It wasn’t as necessary as we continued to build out the fund administration product as we moved into private equity.
The complexity of the firm products that we provide, the acquisitions that we’ve done, um, that now help us in like an upsell cross sell motion as well, have just made things. We’ve also moved up market in each of these spaces, so everything has become a bit more complex that sort of drove the need for, um, that part of the organization.
So. What it coulda, shoulda, maybe a touch earlier, but it felt like, you know, one of the things we’re, I think we’re very good at Carta is like doing the analysis, using the data, figuring out what’s working, what’s not working. Henry preaches to us to learn and move and pivot quickly. Uh, so when you need something, like figure that out and take action.
And one of our oppis is bias to action. and so like I think we did it around the right time it felt like, but. It’s fun to be, uh, Monday morning quarterback on some things like that. Right?
Scott Barker: For sure, for sure. So talk me through the evolution of Carta. So you start with this cap table product. I imagine the go-to-market motion was, was fairly, standardized. You know, I’m sure you had like SMB mid-market kind of enterprise teams, but then you kind of go multi-product.
You didn’t. All right. Well,I won’t put words in your mouth. So it was all the same team.
Carta’s GTM evolution: How Jeff scaled from one rep selling one product to multiple teams across three business lines.
Jeff Perry: In theory, yes. It was sort of individuals that had different levels based on things like their tenure and career and their comp levels, but we didn’t have lead routing associated with the levels within. And so it’s one of the first things I did as I talked to some of the new employees that I had just inherited was like, tell me about your day.
And I met one of our, um, uh, most senior salespeople at the time who was very, very experienced. And his, you know, he told me about his day, which was. I literally have no time in between demos. I’m doing like 15 demos a day, and they’re all SMB contracts that are, you know, a couple thousand dollars, lower ACV.
Uh, so I put, you know, I banked that in the back of my mind, like, okay, here’s my most senior person and he’s working on all these really small SMBs. And then my next meeting was with a, uh. Fairly fresh out of college, younger, uh, excited, enthusiastic about career and learning. And she proceeds to tell me about her day, which is, you won’t believe Jeff.
I’m working on the biggest enterprise deal that Carta has ever done to this point. So, of course, I’m banking that like, okay, I have my newer, less experienced, probably less prepared person to do a deal like that instead of the enterprise guy that should be doing it. So there were just some, like, from my standpoint, like Carta was amazing and the folks that like got it off the ground and were
selling the very first cap table deals a couple years before I got here. Like they did the really hard work to get Carta going. I got to come in and use and leverage some of the things that I had learned and the experience that I had had at other companies to help put some process and structure in place, to make it hopefully more efficient.
And then, then try to do that in a way where you don’t suffocate the startup like spirit of the company. Like no one wants the big company guy coming to do like a ton of extra process on top of everyone. So trying to keep that like startup vibe to it, while also instilling a bit of structure and process to help make it more efficient.
Scott Barker: Yeah.
Jeff Perry: Yes, now we do have segmentation of SMB, mid-market enterprise, et cetera.
Scott Barker: I love that. And then have you taken that a step further? Like do your sellers, if they’re enterprise, can they sell like full suite or do you have like the fund admin team, the private equity team, kind of the cap table team? How, how is it kind of structured?
Jeff Perry: It’s a good question. We don’t sell the full suite from all the different products, so it may be better if I just quickly explain like Carta in the, um, sort of the, the three company format. So the cap table business is roughly 40,000 companies on the platform, and now we’ve created additional products as well, like total compensation, our QSBS tax advisory product.
So. The reps that are part of the corporations business that sell cap tables, they are able to sell the full suite of product for the, the companies, the, the portfolio venture backed portfolio companies. And then we have the fund administration business, which is over 2,500 firms. and over now 12,000 plus, uh, entities on, on that fund admin platform.
And that’s doing back office software and services for, The ERP, which we call it now for the office of the CFO. and that also we’ve acquired tactic for, fund formation and reporting and, um, we’ve added a tax product. So inside of the fund administration team, if you’re in that team, you can sell the suite of products for fund administration.
And then we have private equity, which is sort of a combination of the two. Um, we have, for years, we had, we didn’t, we didn’t even know why inbound portfolio companies, LLCs of private equity firms were coming to Carta and they would use the cap table product because it was good enough as is then to help them track their membership challenges.
Right. And they looked and operated many of them, very much like a venture backed C Corp. So the product was good enough to help them at the time. We’ve since enhanced that product for portfolio companies, and then we have products for the PE firm. And including fund administration for PE firms too. So, uh, inside of the house inside of Carta, they can sell the multiple products as well.
So it’s very much like, in many ways, like my day is almost like three different companies. However, they’re also interconnected because of the portfolio companies and the investors. So the, the, the founders and the funders and the investors of the funders. Right.
Scott Barker: Mm-hmm. Yeah, I imagine. It’s like three separate businesses, but each one is sort of a flywheel. You, if you, you know, get someone on the cap table. Software then, you know, you can go and approach their VCs and be like, Hey, we just signed your great portfolio company. And so I imagine like from a demand generation standpoint, it must be super interesting to see that flow between the, between the three and then is.
Are all these like three businesses also backed up by their own marketing team, product marketing, different BDRs, different operations, sales ops, maybe. or do those float a little bit more?
Jeff Perry: I would say for most of that question, they, um, they’re sort of specialized, right? So there’s. Product marketing. There’s demand gen. Uh, there’s a marketing team that, um, you know, obviously sits under our CMO. Um, but her team is structured in a way to how we support companies, uh, or, you know, private companies in the corporations business, or how we support fund administration or how we support private equity.
You know, corporations, venture capital, pe. The one outlier in that I would say is, um, enablement and operations. They’re more of like a platform service that helps support all three of the businesses inside of those teams. They have some specialization for each of the three, uh, but there’s a lot of just crossover knowledge that has to happen as well.
So they work and integrate really well with each of the teams.
Scott Barker: Yeah. Yeah. I think this idea of team specialization by product or by vertical is becoming more common, and I think it’s a really good, a good trend and just a better experience for the, the customer and the, the prospect
Jeff Perry: Yeah, you’re so right. And that’s one of the, you know, the main focuses right now is especially around the implementation process, it’s so important, um, especially for, you know, we implement hundreds of portfolio companies every month and like. Then off to a good clean start with Carta. Um, as you know, fund administration, like working with a provider that has software and services, the implementation process is really important for the upsell and cross sell in the future. What we’re finding now is, it is so much more prevalent, even in the PE space where Carta is a bit newer there. But we start working with the portfolio company, uh, and we need to make sure that that implementation process with that company is seamless and smooth.
So they have a great experience because obviously we want them to go tell their PE firm. How great it is that the PE firm then tells all the rest of the portfolio companies that they should be on Carta too. So, um, all of this sort of stems from like creating the best possible customer experience that you can
Scott Barker: Yeah, I think that’s something that card has done, done really well, and it’s, it’s kind of a nature of. the space you play in is, you know, of course you are a, a software platform, but there’s so many nuances in the world that you, you serve that it’s really, really important to have that, you know, business partner, whether it’s a great customer success rep or a great like professional services team that just can be there to respond.
’cause sometimes these. decisions or actions being taken within the platform are very meaningful for the people that are, are taking them. And so sometimes I want to talk to a human. And I think what that has done is really pushed your team to almost act more like a tech enabled services company, which I think most software companies should act more like.
Jeff Perry: Yeah, no, it’s a great observation. And you know, um, admittedly, I think we’ve, uh, we’ve made some learnings along the way where at one point we felt like we can do everything in software. I. And because the software was so good and so helpful and so valuable that we could sort of force that. And the reality is like it does a lot of that for some pockets of the business.
There’s other pockets, fund administration as an example where, um, the, the software is amazing and it helps with so many efficiencies. It eliminates so many errors. And the best part is like when we find an error in the software for one fund and we fix it. We’ve fixed it for 2,500 firms because it’s fixed in the software, right?
And so it allows us to do that and create those efficiencies. But we also are very aware that there’s gonna be a Sunday afternoon when, you know, Scott or Max wants to talk to someone from their team at whatever firm they’re working with. And like that person needs to be available for, for what they need.
And, so we’re trying to create the best of both worlds by leveraging the software combined with the services.
Scott Barker: Yeah. So, so huge. And I think that that alone can be such a competitive advantage as everyone tries to automate and use ai. You know, if you’re the quickest to respond with an actual human, uh, people will, people will remember that if that’s the way they wanna do it, you know, of course, like.
Self-serving. The answer is great too, if that’s how they want their solution, provided. But, all right. So this one will be, uh, this question’s a bit vague. but you know, I think there’s a lot of revenue leaders that would love to mirror the run you had at Carta, you know, starting at 20 mil, you know, going up to $450 million
What advice would you have for revenue leaders who are maybe stepping into a role. That looks a lot like, you know, the role you stepped into at Carta six and a half years ago.
Scaling revenue from $20M to $450M: Advice for CROs entering growth-stage companies.
Jeff Perry: Yeah, it’s, um, I think, you know, the without, uh, you know, sort of a most profound answer for you, Scott, is like. You gotta embrace like the moment and the opportunity that you’re given. And look, I would love to say, I think I chose Carta for what I thought were the right reasons at the time. And we of course all hope that like you pick the startup and you get to go make an impact and it’s gonna turn into this amazing generational company.
The reality is like that doesn’t happen in most opportunities. Um, so for me, I feel very fortunate that, um, we’ve been able to grow and build, um, to where we are now. But it also, it, you know, there’s steps along the way and I think there’s things you learn along the way and how you, uh, leverage the people that you have.
I mean, I still have a large portion of the original team that I inherited here, uh, six and a half years ago, many of which are in, uh, completely elevated roles from a responsibility standpoint, um, than they were at that time. And I feel like we’ve been able to sort of blend the balance between leveraging the institutional knowledge and the internal expertise, allowing them to grow inside the organization, and then supplementing, um, different experiences from the outside.
Like, I can’t ignore, I got to be the benefactor of that. Like Henry deciding to bring in someone from the outside at that time. So there are moments for finding the right people for the right stage that you’re at. Uh, and then I think you gotta just be like. Always thinking about a couple things as your decision making.
’cause my day now is filled with different challenges that come to me and like what do we do to help solve and remove barriers that are in front of the team? And if you’re making the decisions based on what’s good for the customer, what’s good for Carta and the business and what’s good for our people, it’s kind of hard to go wrong.
And so I sort of start every decision making process with that as we’re figuring out like the next thing to do or the next challenge to solve. Are we? You know, as a customer, Carta and our people, and if we can answer that question, we’re probably headed down the right path. It doesn’t mean we’re not gonna tinker and, uh, and evolve whatever decisions are made, but like.
That’s how I’ve chosen to take advantage of the opportunity that I was given. And I didn’t know everything when I joined Carta. I had like my Oracle and my DocuSign experience that I’m grateful and thankful for, to leverage upon, um, and, and, and rely on when needed. Uh, but I was faced with, with completely different, uh, obstacles when I got here.
And, um, you figure it out and you lean on good people. One of the things that I’m admittedly guilty of is like, I like to get input from people. You could argue sometimes with too many people, but that’s because I want people to have a voice, uh, be able to communicate like what they’re seeing, what they know, what they’re learning.
I want them to feel empowered and compelled to like, speak up and share their experiences and help be part of the decision making process. There are times where too many opinions isn’t great either. I get that. And so that’s where I have to kind of mediate, uh, where that happens. But I think we’ve created a great company and a great organization, and that starts with Henry challenging people.
To think and do the best work we possibly can. So, uh, I’ve been lucky. It’s been a fun ride. I feel like I’ve gotten to contribute and make an impact, and that feels good too. Um, but it’s definitely not a one person thing that makes all this happen, that’s for sure.
Scott Barker: Yeah. Yeah. And you’ve, well outlasted the typical tenure of, uh, A-C-R-O-C-R-O in the software space. So congrats, congrats, on that. Um, and yeah, I think one of the
Jeff Perry: I think that’s a myth, by the way. Like it doesn’t have to be, I, I, well, to me it doesn’t have to be that way. Right? Like I’ve heard it all. I’ve read, I mean, I think at one point Henry talked about how 18 months is the lifespan, blah. Like, it depends, like it’s the person, it’s the role, it’s the company.
There’s so many variables to it. Um, you know, I, I’m, I feel fortunate that I’ve sort of navigated all of that and found a way to, to contribute and keep building the teams and growing the business and. Uh, doesn’t mean every day is easy, uh, by any means, but I love the challenge of it too. I think a lot of it comes from growing up, like playing baseball in college, like having, having sort of the competitive spirit, like I no other way than to like, keep, keep the battle going and, and keep fighting to, to try and win and try and help my teammates win.
Why “big company” people can thrive in startups—if they leave their playbooks behind.
Scott Barker: Totally. Yeah. And something I appreciate about you as a leader is, you know, to go the baseball analogy, like you have the fundamental skills and the fundamental knowledge to play the game, but every game is very different. You know that your opponent is really different. Like you’re in different circumstances and I think we’ll call you at one point a big company guy in Oracle.
You know, big company people can get a bad rap for trying to take the systems and the process that worked at an Oracle like company and put them into startups and they get really attached to this ’cause they saw it work. They’re like, no, this is the way, this is the like, earned secret that I have.
And that can really be the kiss of death. And I think that’s why, you know, sometimes that’s a black eye on that, that style of leader. But it really does sound like, you know, you’ve, you’ve taken the Oracle experience, you’ve taken the DocuSign experience, but you still started. Basically fresh at Carta, and you wanted the input from customers, you wanted input from leaders, and then you built the strategy versus coming to the table with the strategy, which I think is really important.
Jeff Perry: Yeah, it definitely is. I mean, you know, if I could give advice, it’s like find the, find the smartest people in the room and that wasn’t me, and help align with them to help understand like. What’s working in the business, what’s not working in the business, where’s my low hanging fruit to make adjustments, you know, improve short term and then like, think more strategically, long, long term as well.
So, um, you know, I found those people, uh, I’ve kind of found ’em every stop of the way, to be honest. Like that’s a little bit of the secret sauce is like, find the right people to, to help surround yourself with so that it’s collective success versus an individual thing. Um, so yeah, I think there’s a couple, um, of bad rap like moments out there, like the whole, like small company to big company person can’t do it like individual based.
I hope I’m sort of proof to dispel that bad rap. Uh, and then the other I think would be like, you know, like a nice guy can’t do the job. Like I think, I think you can, you don’t have to be like the hard ass all the time. You can have compassion and empathy and all the things that go into it.
You also have to be firm and direct when needed as well. Uh, and there’s a time and a place for each of those, uh, styles and how you communicate. Uh, and that’s both with individuals or more broadly with the entire team. and I think those are things that you, not necessarily a skill, but just things you learned through observation along the way.
I took the best of what I learned from many of the great leaders that I worked for at all three companies. And then I took some of what I didn’t like and I saw in other people and tried to say like, I’m gonna do more of what I liked and what resonated and less of what I, what I don’t, to try and make it like your own style and how you operate with people.
And you can still be a decent guy, but also like to direct and hold people accountable, and take ownership of the organization that you have.
Scott Barker: Yeah. Couldn’t agree more. Yeah. So, one thing I wanna talk about with you, and I think this is a good segue, is. You know, you can lead with compassion, you can lead with empathy, but you still have to, you know, hold this really high bar for people. And, and, and it’s okay to demand, you know, excellence and excellence is gonna look different for everyone on, on different days.
but I know performance management is something that you think a lot about. and I would love to get kind of your thoughts around performance management. ’cause that’s a way that You can show up on your one-on-one, empathetic and, and compassionate, but everyone kind of knows where they stand when you’re managing performance in the right way.
How to use PIPs to coach—not just cut—and what most orgs get wrong.
Jeff Perry: Yeah, it’s, uh, it’s definitely a hot topic for us. And, you know, it depends on how you look at it. Performance management can be easier or harder as a sales leader, a revenue leader. ’cause you always have the scoreboard out there on like, how you’re doing, like revenue metrics wise. So it’s all the other things that go into it.
You know, frankly, what ends up happening is, top performers, not always the best managers. So they don’t know how to performance management because they were top performers. Or sometimes a top performer becomes a manager and they’re actually really good at that too. But they were never performance managed ’cause they were a top performer.
So how do they know how to do that with someone else to actually like. Really help them improve or manage them out of the business if, if that’s what you know has to happen. And so, um, making sure that you have great HRBP, uh, partners as well, um, the documentation of, um, the communication that happens and the coaching that happens, and that can be positive and negative.
Not every performance improvement situation leads to a departure. Um, but it can lead to like turned around opportunities that are taken advantage of. And I think like that. When not done well, it just leads to obviously bad performance by individuals and by teams. It leads to bad team culture, uh, that then bleeds through or can bleed through the organization and it leads to potential HR issues and, and legal issues that become a drag to the entire organization.
So I think the more we can help, especially like. Early stage frontline managers with performance management, I think helps the organization be healthier and stronger. Um, and it allows for us to be much more efficient ’cause you avoid other issues that can arise from it.
Scott Barker: Yeah. Yeah. Do you have an example? Uh, and I’m sure you do through your, you know, long, long tenure of a successful. PIP program where someone turned it around and started killing it. ’cause I think hopefully in this episode we’ll just go through every misnomer out there in tech and try to try and refute them.
’cause a lot, there is a school of thought like, oh, if you’re on a pip, you should be starting to look for a new job asap.
Jeff Perry: Yeah. I’m so glad you asked. And, uh, I’m sure a couple of these folks are gonna watch this and know who I’m talking about, but I’m not gonna say their names. But, uh, when I joined Carta, uh, you know, like classic like. Evaluate the org, uh, you know, the product, the, the customer base, the people like who’s performing, who’s not, what’s working, what’s not.
Um, and there were a couple, you know, a couple individuals that like, actually I really appreciated the transparency. There were a few frontline managers that came right to me and said, I actually don’t really wanna be a manager, but like, they needed me to, as we were growing quickly. And I was asked to, so I filled in and I was like, well, that’s good.
I’m gonna put that in the bank because like, I love that you’re honest about it, but if you’re telling me you don’t wanna be a manager. This isn’t gonna work for me longer term. Like I need people that live, eat, and breathe like being a manager and helping other people be successful. So it’s fine that it was a bridge for you, but it’s not a long-term thing for me as I’m thinking about building the sales org at Carta.
So I had a few of those scenarios. I had a couple like specific individual people that I. I was told aren’t performing well, and you know what? The numbers on the page were exactly right. Like they were not performing well. Um, but I asked for a little bit of grace, uh, and some time period to let me like get to know some of the people in the organization and figure out like why they weren’t performing well and what was working, or in this case not working, to suss it out and see if I could, I could help.
And maybe it would’ve been the same result of like. Two months later, still wasn’t a working plan, not hit, and time to depart. The reality is like, I couldn’t be more proud of the two folks that I have in my mind that are here six and a half years later, like incredible performers, huge responsibilities across the organization.
And they could have been easy, like, yeah, this isn’t working. And after a year or so at Carta time to move on and instead their careers are thriving as a result of people leaning in. Uh, and trying to understand how and why we can help them be better successful. And my guess is as we did that with them, we didn’t even know, but we were helping like other people as well.
So it’s pretty cool. It’s the fun part of a career, right? You get to try and help. Like, and it doesn’t work for everyone. Not everyone’s made for sales. Not everyone’s made for, like, we’re a, we’re a fast-paced, high thriving environment. Like not everyone’s built for that, and that’s totally okay.
there’s plenty of other roles inside of companies for different people or plenty of other different companies for people, if that specific culture doesn’t work for that individual.
Scott Barker: Totally, totally. And it only takes a few of those examples where people see. That leadership has really rallied around someone and turned them around and, and, and had a really big impact to kind of get rid of some of the fear because there’s, there’s, there’s some fear in, in sales. You gotta hit this number and you’re always worried about your job if you don’t, you know, perform this month.
And if you see that, you know, people have your back, it just allows for more creativity, more experimentation and you know, people just enjoying their job more, which is huge.
Jeff Perry: You know, the other really cool thing about it is now that we’re a couple years removed from that, one of these individuals I of course asked questions like were being asked of him at that time. Like, yey, how about so and so? How are they doing? And the response has been like I’m that person.
Remember six and a half years ago how you felt about me at that? Like, I got this like. Let me give this person a shot to like let us coach ’em. ’cause I think they’ve got what it takes to be successful here. So another like getting to pay back what was paid forward to them, which I think is pretty cool as well.
Scott Barker: I love that. In those cases, did you find that it was more about, kind of going back to the basics and, and reteaching them the fundamental skills? Or was it really just like someone believed in them and like spent time with them? Um, what were some of the key unlocks in your eyes that made them make that successful transition to a, you know, all star rep?
Why the best sellers are quarterbacks, not lone wolves.
Jeff Perry: This isn’t a question dodge by any means, but like obviously it’s, it’s a little of both I think in, in scenarios or there’s other variables too. You know, a couple of examples I’m thinking of, like, there were some basic, like I. lead routing issues that weren’t getting like the same amount of leads to people at the appropriate time.
So like, it actually alerted me to some of the organizational things that we needed to help get the same opportunity to an individual, uh, to help make sure they had the opportunity to the same amount of at bats to be successful. Right. Um, and the other, uh, example, I think it was purely like someone that maybe started in a role, a touch in over their head and like.
I need someone to say you can do this, and by the way, you don’t have to do it alone. Like and I, that resonated with me the most because I was, I think, maybe a halfway decent sales rep at Oracle back in 2003, I guess it was. But I could not have done it if I did not have a few of the people that were around me.
And in many cases, like some of them younger than me. That was helping me with, like literally, how do I create a contract? This customer said they have two processors of database. Like what does that mean? Like do I add management packs to that? Like I learned from people that were a couple years younger than me. I had sales consultants that literally I would not get on a single call without them on the call to help support me in case I was asked that very technical question that I would’ve been so embarrassed that I didn’t have the answer for. And so sometimes you just need the network around you to be supporting you to make you feel like, oh, I can do it.
I have the tools and the resources around me to help. And frankly, it’s a lesson that we teach everyone now. You don’t have to be the hero. Like anyway. There’s not a single sales organization where someone’s expecting you to go win the deal alone. In fact, don’t tell anyone about it.
Don’t be transparent about it. Don’t involve anyone else from the exec team or from the technical team or from product to help you win the deal. In fact, it’s quite the opposite. You would be shamed if you didn’t include all of those people to help give you the best opportunity to have a chance to win.
Right?
Scott Barker: Totally. Yeah. I feel like, uh, that’s what sort of separates good or mediocre salespeople from, from great is like the mediocre or good ones will. They have this misguided view that their job is just, you know, I go and I sell and I put my numbers on the board and that’s it. And then, you know, the great ones are, no, I’m here to unlock all the resources at my disposal, play quarterback, call a play, pull in the right, you know, players and, and execs when I need them.
And, you know, in that style of selling, you’re, you’re more of a facilitator or a coordinator of using all the resources at your disposal.
Jeff Perry: Like be the quarterback of the deal. And frankly, like I, I’ll admit this, like I was motivated by fear of failure. So I was like, I don’t wanna fail, so I’m gonna get as many smart people to help me not fail. And, uh, that recipe worked for me as opposed to like trying to be the, the lone ranger. Close the deal on the last day of the month and surprise everyone.
I did it on my own, right.
Scott Barker: Yeah. Yeah. And then I’ll, I’ll highlight something you said in that answer too, of just, I think it’s our job as, as leaders to, to. Step one, uh, before, you know, the PIP is like, let’s go evaluate and make sure there’s like a fair playing field. Like you mentioned, like lead routing and things. Like nothing SAPs motivation more than, you know, Joanne gets, you know, 15 leads a month and I get four and you’re just like, you’re, try not to complain ’cause you want the whole team to win, but you’re like, this is, this is bullshit.
So making sure that the territory is better territory. You know, like I, I’ve lived through all of that and there’s some merit and validity to some of it and others, like otherwise, sometimes it can just be like, excuse making too. Right? And so you gotta move past all those things.
Totally. Totally. Well, this is awesome. Jeff, I could, I could pick your brain for hours and hours, but, uh, as we kind of come to the end, I wanna get, uh, one of my favorite questions to ask, and , again, it’s an intentionally vague one. But the question is, what is one widely held belief that CROs revenue leaders believe to be true today that you think is bullshit or no longer serving us?
Pick up the phone: Human connection wins in an era of AI and automation.
Jeff Perry: Yeah. Um, there’s a few, uh, one of ’em would be like, the nice guy can’t do it, which I already touched on, so I’ll save you that one. Um, but I think, sort of this notion of like, everything is automated, and like that’s how it has to be done now, whether it’s through AI or all the different tools we have, and I think like the BS in all of it is like being the person that picks up the phone.
And call a customer and use every possible interaction point you have to build a stronger relationship with a customer, not looking for the sale at that moment. If you do it right and build the right relationship, and you’re adding value and you’re educating a customer. You’re telling them or sharing something with them that will make them smarter because they gain that information from you.
That’s the building blocks for getting the next sale at some point down the road. And so I don’t think everything’s gotta be about like this automated thing and speed. It’s gotta be thoughtful and meticulous and how you go about every interaction that you have because frankly, you get limited interactions with customers.
Their days are filled with their other vendors or their own job at hand. You gotta use those moments wisely, and maximize the time that you have with them to be a valuable, like trusted advisor for them.
Scott Barker: Yeah. Yeah. Great. Great advice. Uh, I think hopefully this, this automation and AI just gives us more time to. Not go and automate more. It’s to get and spend more time with our customers and, you know, being human. Um, which is, which is great. Well, one thing I do want to highlight, ’cause I just gotta give kudos where, where credit is due.
For all those listeners who might be also interested. You know, we talk a lot about go-to-market, but we talk about venture as well. You guys put out some incredible kind of reports. Uh, I really like them and I know you’ve got a VC fund performance one coming out. I think it’s, uh, March 20th or something.
And so if anyone is interested in benchmarks across, uh, VC funds, et cetera, I would, uh, highly recommend, you check out, uh, some of the reports. That’s a cool part of. Kind of the evolution of Carter. You guys are just sitting on this treasure trove of incredible data and insights, and it’s cool that you’re starting to publish them in a big way.
Jeff Perry: Yeah. Well thank you for putting that out there. Um, we do, the amount of data is incredible. We have a great marketing team that, um, uh, that helps with a lot of this. And, uh, if you don’t follow Peter Walker, you should, he’s our in-house. Uh, data, uh, analyst who has, uh, quite the following of his own now because of all the insights that he’s putting out, um, for, for founders and funders.
So I’d recommend following him for sure. Um, and of course you can always reach out to me, uh, if, uh, I can ever help with anything, uh, Carter related or anything else.
Scott Barker: Perfect. Yeah. I highly recommend that. Follow and follow this man. Of course. Uh, on, on LinkedIn. Jeff, uh, last thing, uh, are you hiring anyone? I’m sure people have listened to this. Maybe this might be a leader I wanna work with.
Jeff Perry: We are always looking at supplementing the team with great talent. So, uh, especially people that have experience with selling into venture capital firms, uh, private equity firms, um, that is the. The next big space for us. So yeah, reach out if you have an interest in Carta.
Scott Barker: Awesome. Beautiful. Well, Jeff, thank you for the time my friend, and for all our listeners who hung out with us. You know, I say it every week, but listening’s one thing, executing something totally different. Hopefully we gave you some ideas, inspiration stories, uh, that you can take into your own business and, uh, we’ll see you all next week.
Jeff Perry: Thanks for having me, Scott.
Scott Barker: Thanks, Jeff.
The post GTM 141: Timeless Growth Tips From a $7.4B Oracle Exit and Scaling Carta to $450M in Revenue | Jeff Perry appeared first on GTMnow.
