Jeff Perry: 0:00

The landscape is totally different now. I mean, back then, companies were on a chase to get to 100 million ARR, and that meant if you do that, you can IPO. And now we're in a totally different world now. And so, like, what is a IPO ready company? And then more importantly, what is a IPO ready and can be successful beyond that is the more important thread to pull there, too.

Rajiv Parikh: 0:24

Welcome to the Spark of Ages podcast. Today we're joined by Jeff Perry, the Chief Revenue Officer at Carta, whose journey from processing paper stock certificates in the most analog way possible to leading one of the fintech's biggest hyper-growth stories. It's an absolute wild, wild story. Jeff is a proven revenue superstar whose career journey spans decades across large enterprise software giants like Oracle and high-growth staff startups like Docus. He is recognized as an iconic revenue leader who knows how to build sophisticated revenue machines that scale with purpose. Under his leadership as CRO at Carta, Jeff has orchestrated a phase of intense hypergrowth, scaling Carta's annual recurring revenue from approximately $20 million ARR to a remarkable $450 million ARR. That's a 22X increase while managing everything from new business and upsell to customer success across Carta's multiple business lines. Jeff attended Santa Clara University where he received a BS in political science and where he also played NCAA baseball. And you can see that team mentality and how he leads. Focus on maximizing your current role, master your craft, and the opportunities will come. Some of the key takeaways you can expect from this episode. How Carta is monetizing its bellware status as it further drives into enterprise sales. What the new definition of fast growth is for startups ahead in 2026. And finally, why Jeff values performance under pressure and those who operate from a fear of failure. Jeff, welcome to the Spark of Ages.

Jeff Perry: 2:03

Rajiv, uh pleasure to be with you. Thank you for having me. Look forward to the discussion today.

Rajiv Parikh: 2:06

So, Jeff, it was so great to meet you at the Go to Market Leadership Society event. You were speaking there about the CRO and CFO relationship, and I love the story. Of course, I'm a fan of Carta. My company uses the software, and it's you know, as an entrepreneur, it hits one of the problems I deal with, which is dealing with cap tables and all the misery around. So great to have you on.

Jeff Perry: 2:26

Well, thank you for being a user. We have you know thousands, millions of fans, Carta fans out there now. Everyone loves getting their sting email with confetti, letting them know they have uh new vested shares. So we take the same enjoyment and excitement with all of our customers, too.

Rajiv Parikh: 2:39

That's right. So just let everyone know, Carta is a leading equity management platform that helps startups, private companies, investors, and employees track and manage ownership, stock options, and fundraising with ease. So the platform digitizes and automates the complexities of equity management, such as cat table calculations, which is the biggest pain in the butt, regulatory compliance, an even bigger pain in the butt, employee stock plans and valuations, giving all stakeholders real-time transparency and a streamlined experience. So if you are running a company, this is something you deal with. And that's how you guys made a name for yourself, right? Was in that initial pain.

Jeff Perry: 3:12

It definitely is, yeah. I actually was reminded by Henry, our CEO, uh, last week in a discussion. The original problem statement to solve was actually reducing or eliminating the shipping cost of sending an actual stock certificate to an employee or an investor. So it was literally trying to like save the cost of UPS or FedEx bills to ship the actual certificate. But what WCARTA really has become is taking a spreadsheet problem or a service problem and putting into software and into the cloud. Uh and we've done that, you know, that's how CARDA got started on the cap table side with stock certificates and then became 409A valuations. And then we've also done the same problem solving on the fund administration side for VC and PE firms, where you have a spreadsheet or accounting practice in a service model. And we've taken that and put that into software and in the cloud as well. And so we built our fund administration general ledger that now serves 2,500 plus uh VC and PE firms too.

Rajiv Parikh: 4:04

That's where the real revenue is, right? I mean, that's not where you started, but that's what's become the main source of revenue for the for the company, growth for.

Jeff Perry: 4:12

That's right. Yeah. The cap table business is still roughly two-thirds uh of the revenue. But as the other businesses have been growing, you know, we we internally joke that at some point the captable business becomes the side hustle for Carta and it's the connectivity of stakeholders and founders with investors. But over time, you know, the the larger opportunities and the future of new products that we continue to add will be around the fund administration platform and this concept of an ERP for the office of a private capital CFO. And that's what we're building towards. So captable will always be a part of it. It's on the front end of the ERP. But the reality is the bigger opportunity is to continue to do fund administration and additional products around that to help serve the office of the CFO.

Rajiv Parikh: 4:51

In a way, it's how people get to know you through a captable product, right? It definitely is.

Jeff Perry: 4:55

Yeah. I mean, most people know of CARTA as you know, originally eShares because, you know, whether they were an employee or an investor of some kind, received a CARTA account and received some shares and equity. That is evolving and changing into that's something that we do and will always do and do very well. But we continue to expand who we work with and broaden that network. You know, we did an acquisition about two weeks ago, uh company called Excelix, which were basically helping extract very complex fragmented data points of LPs and pull that into one seamless report for them. So we're working with founders and captables, CFOs for venture capital and private equity firms, and now the LP community as well.

Rajiv Parikh: 5:32

That's great. So it's you're you're building off that network base, right? As you have this interconnection. So Carter CEO Henry Ward, as you mentioned earlier, has noted that founders often make the mistake of spending heavily on sales too soon, which can mask bad product market fit. So when you were reorienting your revenue teams after the 2021 boom and facing potentially volatile macro environment, how did you decide what was necessary go-to-market expense versus an expense that might hide underlying friction? And what non-revenue metric was key to ensuring your sales reps were focused on must-have value rather than just closing deals?

Jeff Perry: 6:08

Yeah, it's such a great question. You know, and you know, whether it's CARTA or any of the stops I've been along the way, there's this old adage of like, if you just add more capacity, then that will equate to more revenue. And we subscribed to that methodology in my first couple of years here because there was product market fit and the inbound flow was was significantly high. Reality is like there's only so many companies being created and only so many companies being funded, which are the time-bound opportunities for them to consider a captable solution. So there's not a lot I can do to help influence that aside from the network effect that we have with law firms and venture capital firms. So we had to change sort of how we think about the business. And it's not just to add more capacity equates to more revenue. It's how do you get more efficient? How do you get smarter? How do you leverage some of the different avenues to source inbound? And so we started working obviously with incubators and accelerators. We deepened the breadth of the long tail of law firms that we work with to solidify that partnership. And so, you know, it's classic Carta, like we adapt, we evolve. So as we're doing that, we're building the fund admin product, we're adding products to that. A perfect example is like, you know, we found that there was a problem with distributing K1s in a timely manner. So we said, you know what, we have all the information inside of our platform as is. Why don't we create a K1 product and do taxes for our firms? And so for us and the team, that's great. It allows an upsell, cross-sell opportunity to existing customers. It allows us to add something new to new business customers as well, as far as the complete offering that we have. And that allows us to expand revenue. And like it's one of the things I love about Carta is we're constantly looking at sort of the three main businesses of companies, cap tables, venture capital, and private equity, and then figuring out what additional products we can add to the offering to add more value to our end user customer.

Rajiv Parikh: 7:47

When you got into that situation of like, so things are flying in 2021. And after that, the market kind of tipped, right? For startups, funding fell, especially with software companies. They were exploding and they were getting amazing valuations, and it kind of cut it all. Everyone, you know, there was a big drop in it. So did you have to cut go-to-market expense, or was this where the new products enabled you to supersede that situation?

Jeff Perry: 8:09

So a little of both, right? So we went through COVID where we did a reduction and then we started to build the sales team back up. And then you realize, like, wow, we can do this maybe a little bit leaner than we had done before, and how efficient can we get in the model? At that point, I think we had um sort of an overlay team selling our total compensation product because we experimented. We thought specialization for that product would be the best way to take it to market as far as the sales organization structure. After probably two and a half quarters or so, we learned that like we can actually have the same account executive sell all the products that we offer to a newbound customer base. And so we got more efficient in the number of headcount that we needed and more efficient in overall resource spend to make sure that we're optimized for the customer experience. And then also think about the investment businesses that we're building simultaneously that become the future growth and the future cap table businesses for us along the way.

Rajiv Parikh: 8:59

That's really interesting.

Jeff Perry: 9:00

You know, and you mentioned uh, you know, a metric that's sort of outside of revenue to measure. One of the things that we've been watching closely over the last several quarters is just a productivity metric around number of meetings had or number of chorus calls we have, Zoom calls by AE per month. And sometimes it's not the best indicator. Other times it's very clear of like productivity. Obviously, like the folks that are exceeding quotas and getting into accelerators and making a lot of money are the ones that have more meetings. And so, like, that hasn't changed in the 20 plus years I've been doing sales at Oracle, DockySign, and Carta. The busier you are, the more customers you're talking to, the more opportunities you have to sell and be more successful. And that formula hasn't changed. So we're watching those activity metrics too.

Rajiv Parikh: 9:43

That's your leading indicator. Like, if you're it is you know, because by the time you get to the end of a cycle, your time to make a change is you know, you're getting stuff way, way later. So this is your leading indicator.

Jeff Perry: 9:52

It is, yeah, because you can track the traditional like number of calls, number of emails, but frankly, like everyone is doing that. And the the sophistication of the buyer has changed with like the introduction of AI and all the information that people can gather prior to getting on a call with with Carta, the customer is prepared. And so doing a cold call might not necessarily be the best way to connect with them, but making sure that you're doing all the things that are within your control to get as many meetings as you can to make sure your calendar is as populated as it can possibly be to give you the best chance to be successful.

Rajiv Parikh: 10:23

That's great. So are you finding the data indicates nowadays that like you were saying, people find you before you find them, right? As uh more Gen Z folks are buyers, they're even more so than Gen X folks, right? And then are you finding that AI is helping you with that as well? Like, are they educating themselves with AI or using AI tools, or maybe it's both?

Jeff Perry: 10:43

It's a combination, not to dodge the question, but it's always a little bit of somewhere in between, right? And uh typical with Carta, I can't always answer one question with just the simple answer because the three businesses are very unique. They're at different stages of maturity as well. So, as far as like captable information and it being readily available, yes, it's a newer generation of founders typically on the forefront of cutting edge technology. And so they've done their research. They typically are working with a law firm or a VC firm that has hopefully recommended CARDA to them as well. Typically, they've worked with CARDA before. So, from a captable standpoint, you're getting a warmer lead or an introduction with someone that is actually understanding CARTA to and what we do. That's also coming true in the venture capital business for fund administration. In private equity, we've spent a lot of time over the last year and a half in educating a market of what CARTA's offering is. And so you sort of meet people where they're at with their familiarity with Carta and what we offer. And I would say almost 100% of the time, people that we talk with, it doesn't matter if it's a founder of a cat table business or a CFO of a private equity firm, they don't fully understand the full breadth of everything that Carta does and offers. So it's an opportunity for us to be a trusted advisor, educate a prospect on all the things that we have to offer and add ultimately add value for them.

Rajiv Parikh: 11:57

So now CARDA successfully utilized a velocity model to win early stage founders and emerging fund managers. However, the current market demands a focus on capital efficiency. As you know, growth rates have generally declined across the SaaS industry in 2024 and 2025. And not sure if you're seeing that as well on your side, but how did the CRO organization pivot its primary efficiency focus from optimizing customer acquisition cost or CAC payback based on a high volume startup deals towards demonstrating long-term growth endurance within the nascent high value private equity segment where a lot of future growth is expected to originate?

Jeff Perry: 12:32

Yeah, well, you nailed it. Cardo was started off of working with early stage founders. And you know, we even created a launch product, which is free for founders that have raised less than a million dollars or have less than 25 stakeholders on their cap table. So we offer that at no cost because the idea is we get them on the platform early. If they grow and they're a successful company, they'll convert to a paid plan at some point. And we want to kind of meet them where they are in their journey of growth, help advise them along the way, have you know a decade plus long relationship with them on their journey to potentially IPO, and we can do all the things for them along the way. We took the same formula with winning early stage venture firms when we started this back in 2018-19. We didn't go after the largest firms in the world that were hundreds of billions of dollars of AUM. We started with first-time fund managers and emerging managers and made sure we won that market, take that cap table formula, apply it to what we did in venture. That's why we have 2,500 plus firms using the Carta uh platform now. Ultimately, though, you're right. Like we have far greater aspirations as a company to be much larger than we are now and to reach those aggressive growth targets. You can't do that solely off of emerging managers or smaller funds. And so you naturally, like most companies, go through this inflection point of I did the SMB thing, now I need to evolve into mid-market, enterprise, and cross-market as well. And so for us, it was working with larger, more established firms, which we're doing now and have been for the last several years, and then working a cross-market in making sure that the offering that we have is also uh applicable and relevant to private equity firms too. So it allowed us to move up and over to continue to earn higher ACVs that help us achieve the higher growth targets that we're we're looking to do as a thriving business.

Rajiv Parikh: 14:11

Yeah. So did you end up getting a different kind of Salesforce or is it the same Salesforce? And then I'm sure your marketing changed as well for it.

Jeff Perry: 14:17

All of the above, yes. Different Salesforce. The profile of an account executive for our captable business is an SMB type profile, very different than an individual that we bring on board to work with CFOs of you know, multi-billion dollar private equity or venture capital firm. So there just takes a different experience set, a different background set to be able to do that. So the profile of the sales organization has evolved over the years to where now I feel like we're optimized to be able to have the right conversations with the right prospects and where they're at.

Rajiv Parikh: 14:45

That's great. So you're borrowing off your experience from you know, you're doing enterprise at Oracle, right? So it's kind of like me in my early days. I was selling computer systems at Sun Microsystems and at ATP. So you had the enterprise sale there, then you have the DocuSign SMB sale.

Jeff Perry: 14:59

Yeah, there's so many things. I guess you don't realize it while you're you're sort of growing up in your career, but so many lessons learned from my time at Oracle and DocuSign that I apply now to, you know, going from SMB to enterprise or doing cross-sell and upsell motions, multi-product, customer success. There's so many things that, you know, I was learning at the time that I didn't realize would be so valuable and beneficial in the role that I'm in now.

Rajiv Parikh: 15:21

Just like you're talking about, you have a simultaneous go-to-market motions with high velocity 14-day cap table sales cycles, right? To 90 plus day enterprise VC funded administration motions. So, what do you find to be the single biggest organizational tension point that this standardization paradox creates outside the sales team? So, like you have RevOps, enablement, marketing, product teams. How do you prevent that internal friction from negatively impacting the customer experience for your largest enterprise clients?

Jeff Perry: 15:49

It's not easy, but I would say that you know, the key to the success of all this is the transparency and the relationships that I've created over seven years now with my peers as part of the exec team. And, you know, I work very closely with Henry and Charlie, our CFO, and Nicole, our CMO, and the product team and Rushali, you know, to make sure that like everyone is an understanding of where we are from a pipeline perspective and the opportunities that are part of it, and also understanding that each of those businesses that I've described, they're at different maturity levels of the pipeline and the consistency for which they they perform. And so, yes, we expect the cap table business to move very quickly and it's very consistent. We have more enterprise-like deals on the venture capital and fund admin side and in private equity that are longer sales cycled and oftentimes very much time bound by a firm either not having a great experience with the current provider and or raising a new fund. And so I can't always control those two time variables. But what I do need to make sure is that the team is in the best position to create relationships over a period of time for when one of those two things likely happens, and we're there to be able to share what Carter can do to help make a better experience for them.

Rajiv Parikh: 16:56

This is the kind of stuff I love. Like you, you know, if you're in marketing, we are always looking for that moment that matters, like what takes someone from their current state to wanting to switch, right? So, in many ways, you're not in a nascent market anymore where they're just you're just educating them. In some places, they have other solutions and now you're trying to switch them over. So, like, how's that interaction with marketing where they're helping you find that intent, the intent of that person to switch, and then turning you on to it? Or you're probably looking at it together, right? You probably look at your calls, you're probably looking at we review everything together, which is wonderful.

Jeff Perry: 17:29

I uh, you know, I feel very fortunate that I have a great partnership with our CMO, Nicole Bayer, and her team because we look at this together. And it and from our mindset, it's a shared number. It's not just Jeff's revenue number, it's our collective number to hit together. But again, the businesses are at different stages. So typically, uh, you know, a cap table lead will come in and the current incumbent is like do nothing or doing it in a spreadsheet. So there's an opportunity for us to insert like what Carta does and how we make that more efficient for the founder. Very different than like the warming of a lead and the educating of a prospect in venture fund admin or private equity that creates that longer sales cycle. We've also, you know, there's SF Tech Week has just happened, LA Tech Week. We try and leverage some of these broader events to do some of our own, what I would call more curated specific events for Carta customers and prospects. And we've been doing a lot of that in the last couple of weeks here, bringing together customers that we know have had a great experience once they've moved from another provider to Carta and have them help share their story about their experience and why it's different and better since they've started working with us. And there's no one better to sell your product than an existing customer to a prospect. Like so them hearing like the truth and the accuracy of their experience has been really, really helpful. Those things don't happen without the support of the marketing team that we've we've now have in place. That's interesting.

Rajiv Parikh: 18:45

In one of our previous podcasts, you know, we were talking about these, you know, the B2B marketing practices. What folks are talking about today is that many of the digital metrics that we're using before, many of the digital methods we're using to reach folks have become a bit saturated, or you need you know you've hit a point of optimization. So now intimate events are actually more valuable than they used to be. Are you finding the same kind of thing?

Jeff Perry: 19:08

Or without a doubt. Uh just got back from an uh intimate event that we did last week with all it 10 customers and 15 prospects. And we brought in the majority of the C-suite, you know, product, marketing, sales, to talk about how we work with customers. We actually, which was I thought brilliant, was we did breakout sessions and actually like work through some vignettes of scenarios that we think a CFO might go through in reporting and ask them to like break into groups facilitated by people from Carta to help with the conversation of like, does this resonate and what would you want to see built into our product? And this is legitimate. Like, we take the product feedback. And later that evening, I was with our CPO and she was already talking to her team about building the stuff that we had heard about just hours before from prospects of what they would need. So it's like moving and happening that fast, and we're able to be that nimble still, even though we've become a bigger company, to say this is what the market is telling us is needed from prospects. Let's go build into the product for them, which is phenomenal.

Rajiv Parikh: 20:05

When you get that kind of cycle time, that's just incredible.

Jeff Perry: 20:07

It's incredible, yeah. But you know, this is also like, you know, Rashali's also been at Carta for I think nine years now. I've been seven plus. So we we have a cadence of working together and understanding, like, we're hearing this, we need your help, and we need involvement from the entire team. This isn't just a sales thing to get you know revenue over the line.

Rajiv Parikh: 20:23

That's great. So you've also at Carta made a substantial strategic move into private credit. Given the general market sentiment that direct lending and private credit offers attractive yields and are set to grow. What specific market saturation or operational thresholds do you anticipate private credit hitting by the end of 2026? And how will that influence the CRO organization and go-to-market resource allocation between VC, private equity, private credit verticals?

Jeff Perry: 20:48

For us, it just became a no-brainer once we started working with all these PE firms and understanding that they have a credit arm as well. And so we've started working with many firms, doing the fund administration for the firm and then also servicing the credit loan component of it. We were doing that through a partnership uh that we had with another provider. Just last week, we announced an acquisition of Cervatis, the company that will now be part of Carta, that will help us service these loans as well. So, from a resource standpoint, like we're putting our money and resource behind making this a great experience for private equity firms that come to Carta for both fund admin and for loan servicing. Now we have the software and the services to be able to do that to answer the go-to-market piece. As I'm doing that, I'm also building out the sales team and the marketing functions with Nicole's help to make sure that we're prepared to go capture this market because we do believe it becomes the biggest opportunity for us, especially over the next three years.

Rajiv Parikh: 21:38

That's amazing.

Jeff Perry: 21:39

We're really excited about it. Yeah, just in the last two weeks, we've done two acquisitions, Celex and Cervatis. So all things helping, you know, the LP community and loan servicing. So all the things that we're banking on for the future and the growth of the company, we're we're doubling down and leaning into.

Rajiv Parikh: 21:53

That's amazing. And so you're not necessarily pulling from one to the next, you're just taking the growth and you're channeling what should be next.

Jeff Perry: 22:00

Yes, we believe so. It's like find the signal in the market and then figure out what do we build to go make it better. And then are there things that we can buy to help supplement our offering to? That's great.

Rajiv Parikh: 22:09

So we're gonna get into a little bit more about like what you see now. You have such a breadth of data that you're seeing from multiple places in the whole investor venture, now private equity ecosystem. So at CARTA, you're tracking essential metrics for your customers, like ARR per dollar of capital raised, right? Capital efficiency to increase productivity, right? It's one of the cool parts about your product. And however, in the AI, with the AI revolution, there's uh massive non-traditional infrastructure investment energy consumption, custom silicon to reduce dependence on hyperscalers. So, as the CRO, do you observe the financial models of AI native private companies which Carter serves as shifting? Do you see that shifting? Is there a requirement for heavy infrastructure investment leading to like a bifurcation of capital efficiency metrics? So different, you're initiating application layer SaaS startups from true AI native deep tech companies that bear high compute costs. So are you seeing that in some of the data that you see?

Jeff Perry: 23:02

Yeah, we do. If you haven't or don't follow Peter Walker, he's our our data analytics specialist in-house here at Carta. He is hands down the best as far as all the information that we have, taking that data and putting it out into consumable reporting, both on the cap table startup side for founders and then also on the venture side. So, you know, what we're seeing is like a bit more time in rounds right now. The rounds being raised are larger, obviously, probably not sharing any like shocking news to you, but that's what the data does, but does show. We also, you know, if on the cap table side, we're seeing an influx right now of companies being created. No surprise, large in part due to all the AI companies being created. How many of those become the next generational companies? Time will tell on that. But you know, we're here to support that growth. There's not a VC firm that I talked to. I was at dinner last night, have another one tonight with different firms and founders where everyone in these venture funds is talking about like investment in AI companies and what you're doing to use AI to be more efficient and maximize what you can do. So all of those things that you hear and feel in the market as you're out talking to people all resonate true in the data that we gather from all the companies on the platform too.

Rajiv Parikh: 24:12

Yeah. So I would think like, so before when you were investing, right, the RD expense was of a certain size, but then a lot of money for SaaS companies would go into go to market. But now when you're looking at these companies that just have massive compute that they have to invest in, they're just like putting so much into infrastructure. So your model is going to change in terms of you're putting so much into infrastructure, you're probably putting less into go to market. And so the whole return on equity model shifts, right? Because before you didn't have as many assets, now you have massive assets. So I wonder how you see that in terms of valuations and how folks look at things. Because one dollar here is not one dollar there. Although right now everything seems to be rising for AI.

Jeff Perry: 24:50

Yeah, it's interesting. You know, I had someone mention to me last night that, you know, through the use of AI, they've gone from 45 SDRs to 15 SDRs. And so interesting thought. Like I'm in a different position and stance on that right now, where to me, using and leveraging AI is less about how do you reduce cost and like reduce your headcount. If anything, it's how do you learn how to use AI to make everyone more efficient and make what you're doing 10x better than you already are, not reduce costs. Now, earlier stage smaller companies clearly looking to be more cost efficient. And so do you spend a dollar less there, put that dollar into RD instead, and do you maximize in a different way? I think that to me is just difference in size and stage of company and where they're at on growth trajectory. And neither is like a right or a wrong. It's just where they're at and where they need to head. Yeah, one thing I find interesting too, the more people I'm I'm out talking to in meetings, like everyone kind of gathers, feeling each other out of like, what are you doing with AI? How about you? And like everyone wants to hear all the ideas. No one has the like, here's the full stack of AI tools that, you know, if you do 150 million in ARR and you have 300 people in your company and here's kind of what your organization looks like, here's the stack that you should be considering for AI. No one has those answers yet. So everyone's kind of phishing, right?

Rajiv Parikh: 26:01

Yeah, it's too uncertain.

Jeff Perry: 26:02

It's too uncertain and it's moving too quickly.

Rajiv Parikh: 26:04

I give my team, I have a 200-person team, and I give my folks a lot of free reign on the operation side to go play with a whole bunch of tools, right? And every quarter when I talk to them, they're using new tools.

Jeff Perry: 26:17

Yes, yeah.

Rajiv Parikh: 26:18

I'm kind of blown away by that. They're using new tools. I did force, not force, but I pushed the answer on well, we have to pick one agentic platform because I want them to unify what they're getting from those tools and turn it into organization-wide processes. So there is this whole thing of there's uncertainty, but you got to choose at some point something.

Jeff Perry: 26:36

That's definitely true. We experience the same thing. And I, you know, it's one of the things I love about Carta. There's such an entrepreneur uh spirit here that people just want to go learn and experiment and try different things. That can also get us into little trouble where everyone is doing all these different things. And so that was starting to happen with AI in a good way, people experimenting. But I love what Henry did and basically said, like, hey, if there's something that you want to use AI, you need to submit a less than three minute video demo of what it is, why it's important, why it'll help us. And then kind of filtering, deciding, okay, is that something we should do? And then if so, is it something we would buy or something we can just build on our own? And so it helped us sort of like streamline a bit of the chaoticness of okay, all this AI stuff and everyone experimenting everywhere.

Rajiv Parikh: 27:22

Because you want to get to a point of reuse, right? If everybody keeps building these agents to do all kinds of things, if they're not looking at it from a reusability point of view, you'll end up building multiple streams of the same thing, which is fun and it's interesting. You want to let that play out, but you also want it to come together and be leverageable.

Jeff Perry: 27:38

So that's right. And most of my visibility to things was sort of the the GTM usage of this. But then you think about the rest of the company, and there's all these other use cases for it that we're being experimented with. But obviously, like, you know, we're embracing it here. And you know, frankly, there's so many ways we're benefiting from it already. My SDR leader has done a phenomenal job and using some tools to help us be more efficient and sort of coverage models and things like that. We talked about earlier moving up market, you get more complicated sales cycles. Oftentimes, those come with RFPs. We have some tools now to to leverage populating RFPs through AI. We launched our own agent to help with performance reviews as well. So there's a lot that we're doing that just wasn't even on the table six months ago.

Rajiv Parikh: 28:19

I literally can come into a meeting and have the whole workup on who the person is, what the company's doing, just a full audit in minutes. It's amazing. So let me ask you about so we've seen, as we know, this massive growth in AI investment. It's like the hype cycles of 99 in many ways, or maybe more recently with the whole blockchain NFT boom. So, from the perspective of what you folks see in your proprietary data, what signal do you look at in the private market to distinguish a financially successful investment or sustainable investment in genuine structural AI innovation from short-term momentum-driven speculation that risks creating a financial bubble amongst AI startups? So, are you looking for a bubble?

Jeff Perry: 28:57

So I you know, I don't know that that's like Carter's role in this looking for the bubble.

Rajiv Parikh: 29:02

Yeah.

Jeff Perry: 29:02

Yeah. I mean, so here's where we feel it. I don't know that it's like it's our role to predict the bubble piece, but like when we know that there are X new companies being created every month and coming onto the platform, like that tells you something is happening out there in the market that is generating more companies being created. And then you see more funds being raised. So we have, you know, repeat fund admin customers that are raising new funds. And the purpose of the raise of the new funds is to invest in AI companies, then that tells you from both sides, the the founder side and the investor side, that there's signal out there that this pocket is being created. Whether it's a bubble that bursts or not is for others to kind of figure out how that plays out and like the actual productivity or you know, success of those companies and the longevity of it more importantly.

Rajiv Parikh: 29:46

That's great. It's interesting to know. And I'm sure that your data analytics group is just looking at the macro data over different times. It must be an interesting study.

Jeff Perry: 29:53

So yes, follow Peter Walker. He's phenomenal. He's got all the data insights for you.

Rajiv Parikh: 29:57

All right, that's awesome. Well, Jeff now comes. Fun part, we're gonna play the game. This is where you get to have a lot of fun with me. Welcome to the Spark Tank, where entrepreneurial excellence meets athletic excellence. And today we're discovering what happens when you combine hyper-growth revenue leadership with hardball heroics. We're thrilled to have Jeff Perry join us at a revenue powerhouse who scaled Carta from 20 million to 450 million dollars in ARR and knows a thing or two about clutch performance under pressure. So, Jeff, you played NCA baseball at Santa Clara University from the diamond to the boardroom. You've always understood that great teams win championships, whether that's a World Series ring or crushing a revenue target. So with the World Series now upon us, we're putting both sides of your expertise to the test with a stat or fiction.

Jeff Perry: 30:43

Okay.

Rajiv Parikh: 30:44

Baseball and business records challenge. We're gonna alternate between iconic World Series moments and jaw-driving private company growth stories. Each question presents a remarkable statistic and achievement. Your job is to figure out who made history, whether it's a legendary player stepping up in October or a visionary founder building a unicorn. Let's see if your ability to spot a winner is as sharp on the baseball field as it is in the revenue trenches. So you ready, Jeff?

Jeff Perry: 31:10

I'm ready.

Rajiv Parikh: 31:10

All right, this is gonna be fun. And as I told you before, I found this hard. So it doesn't matter how many get right, we're gonna have fun with this. So round one, World Series edition, uh the business connection. All right, here's the stat in 1919. This team became the first franchise to sell World Series radio broadcasting rights, pioneering the concept of media monetization in sports. What makes it unique? This deal laid the foundation for the multi-billion dollar sports broadcasting industry we know today, transforming baseball from gate revenue into a media empire, a business tie-in. Just like early tech companies figuring out digital advertising, this team invented a revenue stream that didn't exist before. All right, which team uh achieved this feat? Remember, this is 1919. Okay, A Chicago White Sox, B Cincinnati Reds, C, Boston Red Sox, or D, New York Yankees.

Jeff Perry: 32:04

D, New York Yankees.

Rajiv Parikh: 32:05

Sure about that.

Jeff Perry: 32:06

No, but that's my answer.

Rajiv Parikh: 32:09

You said it with such certainty.

Jeff Perry: 32:11

I didn't know if you I think I might be right, but we'll see.

Rajiv Parikh: 32:13

All right. Actually, the answer, and I was surprised about this. I would have picked the same thing as you. B Cincinnati Reds.

Jeff Perry: 32:19

Oh, wow. Interesting.

Rajiv Parikh: 32:21

Yeah, the Cincinnati Reds were pioneers in sports media monetization, understanding that broadcasting games could create new revenue streams beyond ticket sales, kind of like how modern SaaS companies discovered recurring revenue models. So who knew was the Cincinnati Reds, the big red machine of they won those World Series in the mid-70s. I used to root for them because I was born in Ohio.

Jeff Perry: 32:40

Yeah, good for them. It's been a little bit of a drought recently, but yeah.

Rajiv Parikh: 32:43

Back then they were good.

Jeff Perry: 32:45

That's right. Yeah. And the red machine for sure. The big red machine was excellent. Yeah.

Rajiv Parikh: 32:48

Okay, round two. Private company growth edition. Here's the stat. This fintech company reached one billion dollars in valuation in just two years from founding. One of the fastest paths to unicorn status in fintech history. What makes it unique? They achieved this by eliminating traditional banking infrastructure and building a mobile first challenger bank that resonated with millennials. Which company achieved this feat? We're gonna give you four fintech companies. A affirm, which is buy and I'll pay later. B Robinhood and Trading. CHIME, low-fee digital banking that just went public recently. D Coinbase, which was in the crypto brokerage market. This is a tough one. So A, B, C, or so affirm, Robin Hood, Chime, or Coinbase.

Jeff Perry: 33:30

Uh Robinhood.

Rajiv Parikh: 33:31

Why do you say Robinhood?

Jeff Perry: 33:33

Because if you mentioned it took on a younger generation, motivated them to be investing, and that's where I went with the answer.

Rajiv Parikh: 33:39

I would have thought so too, because I thought, yeah, Robinhood exploded during that time, especially in what 2021, 2022. Actually was Chime.

Jeff Perry: 33:49

Wow. Okay.

Rajiv Parikh: 33:50

Yeah. I mean, who knew? They hit unicorn status demonstrating how fintech startups could leverage mobile technology and simplified user experience to capture market share from traditional banks at unprecedented speed.

Jeff Perry: 34:01

Wow. Amazing.

Rajiv Parikh: 34:01

I frankly I could have picked any one of these four.

Jeff Perry: 34:03

Like all very successful stories.

Rajiv Parikh: 34:06

Super fast growth. So that was a tough one. Round three, World Series edition, the pitcher power play. You're gonna go back in history on this. So the stat, only 15 home runs have been hit by pitchers in World Series history. But these two pitchers have each hit at two home runs in World Series play. So they account for four of the 15. What makes it unique? Since pitchers are notoriously weak hitters, as you know, having two World Series home runs represents an extremely rare combination of pitching excellence and hitting ability. Here's the business tie-in. Like a founder who excels at both product development and sales. Imagine that rare dual threat capability that creates competitive advantage. Which pitchers achieved this feat? A Bob Gibson and Dave McNally. B uh Sandy Colfax and Whitey Ford. C, Joe Blanton and Kurt Chilling. D, uh Babe Ruth and Walter Johnson.

Jeff Perry: 34:59

D.

Rajiv Parikh: 35:00

Yeah, I would think so too. Freaking Babe Ruth was one of the best hitters and pickers ever, you'd think.

Jeff Perry: 35:05

Yeah.

Rajiv Parikh: 35:06

But it's it's A, Bob Gibson and Dave McNally.

Jeff Perry: 35:09

Oh, really? Okay.

Rajiv Parikh: 35:10

I can't I couldn't believe it. I was gonna tell you like, don't say Joe Blanton and Joe Kurt Chilling. Those were AL, like Kurt Chilling was an AL pitcher.

Jeff Perry: 35:17

Well, until he was with the diamondback. That's true. That's right.

Rajiv Parikh: 35:19

But I don't think he was much of a hitter.

Jeff Perry: 35:21

Or the Phillies. Yeah, yeah, you're right. Actually, no, when he was in the World Series, he was Red Sox. So yeah, that's right. He really wouldn't have been, he would have been DH4 then. Yeah. I like the game. I'm just not very good at your game, Rajiv.

Rajiv Parikh: 35:31

I think the game is great, and I'm sorry you're not getting, but it is fun, and I'm learning a lot because I frankly, like you, would have gotten all three wrong. So Bob Gibson and Dave McNally were the only pitchers to hit two World Series home runs each, demonstrating rare versatility. They were the shoheotani of their time. Like business leaders who master both technical execution and commercial success, these pitchers proved that elite performers can excel across multiple domains, a valuable lesson for today's modern full stack executive. All right, here's number four private company growth edition. And again, this one's really hard too. So they didn't give me any layups. Here it goes. The stat. This company grew from zero to one billion dollars in ARR in approximately five years through pure product-led growth with no traditional sales team for most of that period. What makes it unique? They proved that exceptional product design and viral adoption could replace traditional enterprise sales motions. Which company achieved this feat? And you have four choices. Zero to a billion AR in five years. A was it Slack? B Figma. C Notion D Canva. As a hint, I've had Bill Mesitis on my show, if you know who he is.

Jeff Perry: 36:48

I don't know Bill. I'm gonna say B.

Rajiv Parikh: 36:50

B, Figma. You would think it would be Figma.

Jeff Perry: 36:53

Someone tells me I'm wrong again. Yeah.

Rajiv Parikh: 36:55

That's what I was trying to idea with that one. Bill Mesitus was at Slack.

Jeff Perry: 36:58

Oh, okay.

Rajiv Parikh: 36:59

And at DocuSign, I think it was at was he? No, not DocuSign. He was at Zendesk. So yes. He was a CMO and CRO there at Slack. And that was one of the big things that they did is it was a pure product left growth strategy. I was surprised actually that they went from zero to a billion ARR without a traditional sales team. I I don't know how you do it, but you know, if you have an amazing product, it can happen. And it proves that viral adoption and exceptional UX or user experience can drive enterprise sales. It's the most amazing thing. Definitely.

Jeff Perry: 37:28

And and drives the network referral effect as well.

Rajiv Parikh: 37:31

I mean, I think that's what you're living in, right? It's that's right. It's that you you guys are so cleverly going after like you know you have the cap table offering and it just allows this network effect that happens. That's just uh I think it's a flywheel that everybody wants.

Jeff Perry: 37:44

That's right. That's right. Yeah.

Rajiv Parikh: 37:46

Somehow Slack did it. Well, I think the way that you would think about the way they did it was because they focused on productivity. And it if you're only working with one person in the company, it's not of any value. And so you give it to two or three, and you have a free version. Before you know it, you have a department, before you know it, you have the whole company jumping in.

Jeff Perry: 38:03

Yeah, interestingly, when I joined Carta back in late 2018, as they were the first year or so, Slack was our largest customer. And there was a point where they were headed toward IPO and wanted to remain on Carta platform uh through IPO and become a public company. We wisely decided to work with them. Henry worked with their exec team to decline the opportunity to do that, which had to have been really difficult for us to decide to do at that time because it would have been such a headline uh win as taking someone from private to public. The reality is, had we attempted to do that, we likely would have failed miserably at that time and created a terrible experience for them, which would have set us back tremendously. And so sometimes that like the shiny object right in front of you, like it's best to say, like, is this the right thing for us at this size and stage now? And so we ended up not, we helped transition them off of Carta to another provider to do the public piece of it. But we had we we worked with them for many years.

Rajiv Parikh: 38:57

I gotta say, that is so ballsy.

Jeff Perry: 38:59

Totally.

Rajiv Parikh: 39:00

It must just hit you during that time. Like, here's a huge opportunity. It takes us into a whole new dimension. We open up that whole market, it's a natural outflow of what we're already doing.

Jeff Perry: 39:08

Exactly. Yeah, and there was, you know, they were the the darling of you know, private to become public and IPO. So to have to respectfully decline and and then sort of admit where we were at from the public offering at that time. I thought was pretty cool. But Henry's done some really, you know, amazing things from that perspective of just understanding like what needs to be done to make the product and the experience better for customers, even if it means sacrificing like revenue or or different opportunities. Another example is about a year before I got to Carta, they had signed so many customers that the implementations team had gotten behind and couldn't keep up with getting the cap tables implemented. So he literally paused sales for, I believe it was about two months, and said, every salesperson is now becoming an implementation person, effective immediately, and helping us get through the backlog to make sure everyone that we had signed up had been properly implemented. It did a couple things. Number one, it cleared the backlog and got us caught up, and then we resumed sales, but it also taught all the salespeople at that time actually what a company goes through to get implemented on Carta. So they were that much better prepared for the call they were doing with prospects in the future because they knew the experience that they were gonna go through.

Rajiv Parikh: 40:15

Yeah, I mean, they gain empathy. It's so powerful. Totally.

Jeff Perry: 40:17

Yeah, I find it such a remarkable move at that time when like the pressures of fundraising and showing, you know, rep posting revenue numbers and saying, like, we're gonna pause revenue right now to make sure we get this part of the business right. Like, talk about a bold move. That that definitely was, and that that was 2017.

Rajiv Parikh: 40:34

Wow. So, Jeff, if you were the CRO in that spot, what would you have said?

Jeff Perry: 40:38

I would have said, Henry, can we maybe go grab a beer and talk about this? Because I'm not sure you're gonna change my quota and target for the team for that time period. So actually he would have extremely reasonable and like always pushes us to always think about doing the right thing. It's one of the things I I love about my experience here is you know, it's not always about the number. Of course, the number is important, but it's about like he calls it inputs. Are you doing the right inputs to make the business better? And that was a perfect example of like do the right input to get the business right.

Rajiv Parikh: 41:08

That's amazing.

Jeff Perry: 41:09

But yeah, we would have had an interesting conversation for sure.

Rajiv Parikh: 41:11

It would have been it'd be great, what? You want to do what?

Jeff Perry: 41:14

Yeah.

Rajiv Parikh: 41:15

And and he even talks about it in some of his conversation between missionaries and mercenaries, right? This is where you have to really go into yourself and say, why am I here?

Jeff Perry: 41:25

And that's a that's a missionary moment right there, right? Like, do you believe in the cause? Are you behind it? Help support it, do whatever it takes to make a great customer experience, and then we'll figure out the next thing from there.

Rajiv Parikh: 41:34

It's a tough test, yeah. And it's a great one. So, Jeff, did you always know you wanted to work in technology? Was there like a specific moment or project that sparked your passion? How'd you discover it? What got you sparked?

Jeff Perry: 41:45

You know, I as you mentioned, I played baseball at Santa Clara University and I was maybe the kid in the category of like don't know exactly what you want to do after college. And so I had an opportunity to start working at Merrill Lynch through a connection that I had. And it was entry level to the Series 7, Series 63, get license, help do trading. I got paired up with a senior broker on the team at that point that I learned a ton from. And that's where I started working the cashier window in the evenings. And we actually had clients that would come deposit cash checks and stock certificates. And I vividly remember one of them being an eBay stock certificate that was, you know, ended up being, I did the calculation worth hundreds of thousands of dollars that I was depositing into this client's account. And I remember this vipable moment of like, do I want to be the person that's trying to help reinvest those shares somewhere? Or do I want to go to one of these tech companies and actually receive equity like that individual did? And so, you know, look, I learned a ton in my time, my short time at Merrill Lynch, and I was I was younger and impressionable at that time in career. But that got me an opportunity to knock on some doors and you know, had a door opened at Oracle. And that's that's where I started kind of in the tech space. And I actually did sales, but for the marketing team, so exhibits, sponsorships for the open world conference, which ended up becoming the Dream Force Conference over time. The, you know, and so that was my first sort of entry into the tech world. I saw this massive partner ecosystem around Oracle and thought, wow, there's all these other companies out there. I then got into the product sales team and I did a little bit of everything from database to middleware products. I moved into the hardware organization when we acquired some microsystems. I always just kind of said, like, keep the doors open and I'll raise my hand to help do and contribute wherever I could. And that always led to whatever the next opportunity was. And, you know, here we are, you fast forward all these years later, and I come to Carta, the company that has eliminated the stock certificate that I was like chasing, you know, 25 years earlier. So amazing story. Yeah, it's funny how it comes full circle, but I've been fortunate to have, you know, great stops along the way, great mentors and people that like took a little bit of a leap of faith and believing in me to take the next opportunity or next responsibility. I had that many times over at Oracle, had an opportunity, you know, with Lauren Al Hadiff and his team at DocuSign to be there, you know, and help grow and scale the SB teams and some of the verticals, and was there through the IPO and then had an opportunity to say, I want to start even earlier and smaller at and Carta found me and I found Carta kind of simultaneously. And one thing led to another, and we're roughly 20 million in ARR and you know, healthy business. But it's like, who would have thought it could, you know, evolve into multiple businesses and multiple products inside of each business? And now the 20 million is 500 million and beyond, and we're we're headed to a billion plus.

Rajiv Parikh: 44:22

Did you know that when you first got in?

Jeff Perry: 44:23

I mean, does anyone know? Like, are you are you hopeful? I remember like sort of last meeting with Henry prior to to signing was at that Dutch Goose in Menlo Park. You know, we we had a beer and a burger and talked about like the potential of the company, and a lot of that has come true, but I would say it's come true differently than like we would have thought in that booth at that time having that burger. It just, you know, it would have been like the cap table business and how that continues to expand and grow and what that leads to. It wasn't as much about, you know, the vent the fund admin business and private equity and LPs and all these things that seven years later we're now, we're now doing.

Rajiv Parikh: 44:57

I don't think any of us would have anticipated, even those who are into tech, that private equity or companies staying private longer would be uh such a big trend. How many, you know, trillions of dollars are now in private markets, not in public markets. We wouldn't have forecast that. I mean, Dodd Frank, that was probably one of the contributing reasons, but it's also that it's easier to get done or stay private when there's pools of capital there for you. So yeah.

Jeff Perry: 45:19

So, you know, when I back in those days when I was meeting with Henry and Charlie, and you know, it felt like Cardo was onto something. This could be, you know, a great opportunity. As it turned out, it evolved over time. And you're right, like the the landscape is totally different now. I mean, back then companies were on a chase to get to a hundred million ARR, and that meant if you do that, you can IPO. And now we're in a totally different world now. And so, like, what is an IPO ready company? And then more importantly, what is a IPO ready and can be successful beyond that is the more important thread to pull there too. Which is one of the things, you know, most proud about is what we built here is being like thoughtful and methodical in how we do it and being at a growth trajectory that you know we we aspire to be, and also you know, at a level of profitability too, so that we've hit both ends of the metrics.

Rajiv Parikh: 46:03

That's awesome. So we always ask our guests to name a historical event or person or movement that inspires you. And you answered, quote, people that perform under pressure, like Tom Brady. I think go to high school with them, and people who are motivated by fear or failure, like Larry Ellison. You didn't go to high school with him. What in particular about them lights you up?

Jeff Perry: 46:24

Well, thank you. Yeah. So yeah, I did go to high school with Tom Tommy back in the day. That's many years ago now. And so it's actually been fun to follow someone that you you feel like you kind of knew as a younger kid and watch progress, and then all of a sudden, life-changing experience, and then you know, uh, you know, the the folks that you know we knew him growing up and you knew he was uh, you know, a great athlete and all these things, but then to watch it happen on that stage and how he handled it is like all of us have taken some pride in as well. And you you just be you can't help but become a fan of sort of the pressure and the microscope that you're under on that stage, and then the ability to like not just do it once, but like multiple times repeatedly demonstrate that consistency in performance. And you know, I've watched enough and I've seen enough on it. Like sometimes he's got to be the guy that had to be probably tougher on teammates and be the guy that's motivating and driving. Sometimes he's the raw-rah guy. And so, sort of knowing your place in this, and I feel like you try to take a lot of that into what we do as sales leaders too, is like you know, you ride kind of the highs and lows, but you also keep this sort of temperament of like you've been there before, you know what success looks like. You know that it's not always easy to be successful, and sometimes you're gonna have some failures, and so you learn from that and you pick up the pieces and you move on. So I think there's a lot I've taken from just watching Tom uh over the years, and obviously it's just fun to root for someone that you you you kind of knew when you were younger.

Rajiv Parikh: 47:39

It's incredible. Yeah, I yeah, I grew up in New England, so I'm a Pats fan, and so I studied yeah everything Tom and Billy Belly Jack have done. So it's amazing. But then you mentioned fear of failure, like Larry Ellison.

Jeff Perry: 47:50

So you know, I actually feel like fear of failure. I've always operated that way. Like I've, you know, I went to Santa Clara University, pitched there. I had a fear of failing because I would let my team down. And if I let my team down, I probably at some point would like lose my role in and and my opportunity for playing time or or time to contribute. And so I always wore this little chip on the shoulder of fear of failure. I actually think that was a taboo statement. There was a time where it's like, if you say that, that's a weakness and like you shouldn't say that. I have since heard more people. I recently read something about Larry Ellison operating that way too. And having worked at Oracle, that resonated with me. So I've always like tried to just embrace it versus like hide that like I I've operated that way and just say, like, yeah, like I don't want to fail. I don't want Carter to fail. I like I want to be successful both personally and I want my teams and my people under me to be successful. So operating with a little bit of that fear of failure, I think keeps you sharp, it keeps you motivated, it keeps some edge to you. For me, it keeps me like energized and excited about what we do and who we do it with. So I'm not letting go of the fear of failure. I'll always operate that way. Yeah.

Rajiv Parikh: 48:54

I think that's a great way of putting it. I it's unique and interesting. And you know, we all wake up as entrepreneurs or business leaders. You know, we have imposter syndrome, right? We wonder, can we keep this going? And what keeps us going? And I promise this, can I deliver it? Right. And every day you have to wake yourself up and say, I can do it. But that fear of failure is one of the motivators.

Jeff Perry: 49:13

Totally. And one of the things I love most about sales leadership is to me, is very much like pitching in baseball. Like there's such an individual component to being the pitcher of the team, yet you're still part of this incredible team sport, and it takes everyone like pulling their own, you know, part of the weight to be successful. But a lot of the onus is on the pitcher to perform and the pressure is on because that they can have a significant outcome, both positive or negative, or influence of the outcome to that positively or negatively. So I've kind of thrived in the pressure of that, which I feel like has translated really well to the business side. But it also I I love the team that I work with and the team that I'm surrounded with. And we celebrate the successes together and you know, we work through the challenges together too. And that's the beauty of the team sport aspect.

Rajiv Parikh: 49:55

So, Jeff, if you could magically make one daily task take zero time, what would you choose? And what would you do with those extra minutes?

Jeff Perry: 50:03

I would say it's probably some of just the like the operational roadblocks that come up. It's not like one specific thing, but like I'll start my day and I'll get some slacks from someone that, like, hey, we have this issue with, you know, someone's comp was not correct, or an offer letter didn't go outright, or the levels the same between this business unit and that business unit for a level four AE. And it's like some of that stuff, it just like it, it's roadblocks, it's it's time sucks. It doesn't just, you know, take my time. I then have to go triage and it loops everyone else in. Also, like we just spent like 20 business hours on this ridiculous thing that frankly should have just been solved really quickly or should have never been an issue. So if I could eliminate some of those things, which I don't really know how to do, they're always going to come up. I think that's a sign of like growing, evolving business. But with that, I would take that and do, I'd like to do two things. I'd split that time. As you get bigger, it gets harder and harder to stay super connected with folks that are maybe a couple levels below. I feel like I used to be really, really good at that. And then as things evolve, it just gets harder. So I'd spend some time there. And then, you know, what we've really learned over the last couple of years is the more time I and the rest of the exec team can be in front of customers, I would use the time that way instead. Yeah, it's cool. It's how you create great experiences, it's how you create raving fans that tell the next prospect that they should work with us. So I would use the time that way.

Rajiv Parikh: 51:24

All right, that's a great answer. If you could swap lives with someone for just one week to see what it's really like, who would you choose?

Jeff Perry: 51:31

Maybe the president. That'd be an interesting seat. I don't think it's you know something you'd want like full time, but a window into that world would be really interesting.

Rajiv Parikh: 51:39

That would be interesting. I think there's something like 30 plus people that arrange president's calendar. Really highly scripted situation where the situation is scripted yet extremely dynamic.

Jeff Perry: 51:50

Definitely.

Rajiv Parikh: 51:51

From subject to subject. So it's it's a it'd be very interesting to sit through that.

Jeff Perry: 51:54

I recently went to the Ryder Cup and I thought it would be fun to like switch spots with a golfer. Then you realize like the amount of eyeballs on you just hitting that one shot would be pretty nerve-wracking. So that could be interesting too.

Rajiv Parikh: 52:08

That is that is very interesting, kind of like a picture, right?

Jeff Perry: 52:12

Definitely very much like that. Yeah.

Rajiv Parikh: 52:13

Okay. What's a social situation that you used to dread, but now you actually enjoy? And what changed?

Jeff Perry: 52:19

I I would say it's probably public speaking. I think, you know, most people kind of dread that, I think. And for me, I now like I really enjoy it. Like I one of my favorite days of the year, a couple days, is our sales kickoff. And I, you know, I look back at my early days, you know, I shared Merrill Lynch and even the early Oracle days where I just hadn't had opportunities to do that. And I would have thought of myself as less confident or the ability to like stand in front of an audience of 500 people and you know, do sort of MC and run of show and do you know, state of state of the businesses and all those things, like that would have been high pressure for me. And now I feel like that's my moment. I love it. It's my chance to like connect with our team and our people and share what we've done and celebrate the successes, and then sort of put a bow on that and talk about like the next year and the targets that we're going after and how we're gonna do it and the resources we have behind it, like kind of thrive in that stuff now. Yeah, if you asked me that 20 years ago, I'd be like, there's no way I would do that, you know? And now I love it. It's one of the things I really enjoy about the job.

Rajiv Parikh: 53:15

That is amazing. I think it's that thing when you walk in, you might be really nervous about it because you're like, Did I miss something? Or something some magical thing I need to say. And then the minute you start, you start to connect with people and you start to look in their eyes and you feel that connection with them. That's when things change.

Jeff Perry: 53:32

So to me, I'm so glad you said that. It's very much to me like when I was in the bullpen warming up to start a game, the 15, 20 minutes before is very much like when you're before you're going out on stage to to kick off an event like that. And you have a little bit of like the rehearsal going on in your head and thinking about the things you want to, the message you want to, you know, communicate. There's a little bit of like anxious energy. There's a little bit of like butterflies, there's a little bit of like keep the chip on your shoulder we talked about. And then all of a sudden, like game starts and you throw the first pitch and you go, or lights go on on the stage and like you take over the microphone and like you start your messaging, and then you have that connection of like channel focus. Like it's you know, when I was pitching, it was like laser focus on the catcher and getting that hitter out. And like you get on stage and it's like, okay, I don't even need the slides. I know my message, I know what I'm talking about, and like you're just because you're prepared and all the practice you put in to make it feel like it's natural in what you do. And so there's a there's so many similarities to to all these things that that come together.

Rajiv Parikh: 54:31

It is amazing. Jeff, how about this one? What's something you're embarrassingly competitive about that doesn't matter at all?

Jeff Perry: 54:37

I don't know. I I I'm pretty competitive. I think about everything. Like I'm playing golf uh this weekend with about 30 dads from my kids' schools that we've been friends with for you know better part of 15, 20 years, and there's two teams set up, and it's like I'm my team, I want my team to win, you know. And does it really matter? No, because we're all gonna go have a great time and it's gonna be like, how's this kid doing? Tell me about you know, where uh how many of them have started college now, so does it matter? No, but it's like later that night when we're at the dinner together, we want to be on the winning team, you know.

Rajiv Parikh: 55:07

Again, give the other guy a lot of crap for of course, yeah, exactly.

Jeff Perry: 55:11

Yeah. So I think you know, it's it's those type of things you learn along the way. Some of us are just wired that way. Like, and you know, I actually think a lot of people that have maybe met me, they didn't know a lot about me. I think a lot of people like Icarta early on thought I was a bit more quiet, maybe a little bit less like competitive. But then once they got to know me, they realized like you don't always have to be the loudest, most outgoing competitive person. You can have like the inner fire, the chip on the shoulders, say like, I'm gonna fight like hell to win every single interaction that we have. And some people are just made that way and others are not.

Rajiv Parikh: 55:42

Yeah, I think you totally nailed it. It's not the one that's necessarily so outwardly boisterous or so outwardly competitive. There are folks that are quiet that are just ridiculously intense. It's not until you get into business for a while. I think even in sales, there's that mental thinking that a salesperson needs to be a certain way. And I find that's just not the case.

Jeff Perry: 56:05

And I, you know, the thing I think I've learned along the way too is like the the best of the sales leaders, I think, are the ones that like, or just people leaders, are the ones that can find the balance in that, right? Like you have the competitive, whether it's louder or it's the more internal one. But then, like, how do you balance that with being like genuine and compassionate and driving and having to give the difficult feedback or giving the rah-rah feedback? And how do you balance that with all the individuals that you work with or even your peers and counterparts and business counterparts that you work with?

Rajiv Parikh: 56:36

Yeah, you you see this in coaching of any sport, right? You see it right in front of you. Some people are just out there and they win, and some people are super quiet and they win, and and vice versa. So it's really interesting. So, do you have a favorite life motto that you come back to and share with friends, work, or life?

Jeff Perry: 56:53

So I grew up in you know private Catholic grammar schools and high school, that's how you know with with Tom. I've always just tried to operate by like the golden rule, like do unto others as thou would like to have done to you. And I feel like that's how I've tried to live and operate. And it also like resonates, I think, very well in the business world. Like, doesn't mean like you have to always agree with everyone, doesn't mean like you're you're always in friction with everyone, but you do treat people like respectfully. You give people an opportunity to share their perspective and and their minds. And if you treat people fairly and respectfully, I think you gain the respect from them along the way that earns you the right to like ask them to go the extra mile for you as well. And so to me, it's like, yeah, we're selling software and some services here, but like I'm in the people business now, like and have been for decades now. And it's like, how do you work with people, whether they're customers or prospects or your internal team?

Rajiv Parikh: 57:44

You have investors, you have board members, all of it, yeah.

Jeff Perry: 57:47

And so it's like, how do you communicate with people? How do you treat people so that they want to be part of what you're doing and building and and they feel like you know, I I the other motto I use is like, does everyone have an oar on the boat? And is everyone paddling their oar? Not just paddling it, like, but paddling in sequence together. So we're we're you know steadying the boat in the same direction.

Rajiv Parikh: 58:05

It's all about alignment, yeah. What's your personal moonshot?

Jeff Perry: 58:09

Well, uh right now it's Carta. You know, I've never thought about it that way. I really haven't. Maybe I should, uh, but I just think about it as someone that kind of grew up in a modest world and I was fortunate to have a great family around me and sort of had the things that I needed and the support that I needed. I try and like pay that back as best I possibly can. And, you know, my hope is that like good things happen to good people. And so I've tried to do right by people in my other stops along my career and hopefully made a bigger impact in doing that at Carta. And hopefully Carta becomes a really big thing. And then that provides some opportunities to figure out what the next thing is to do to make an even bigger impact. And whether that's in like a similar role or a different type of role, but what we can do to like continue to give back and help. Like I'm wired that way. Like, I'll spare you the names, but I can give you the names of people along each of the stops of the way that gave me an opportunity to do things that I probably didn't deserve at the time or had an opportunity to open a door here or there. In a lot of ways, the things I get to do now and will get to do a lot more of in the future is to pay that back by creating opportunities for for other people as well.

Rajiv Parikh: 59:14

I think that's one of the most amazing parts about hitting a certain level of seniority in your role is that you're actually paid to give back. You're actually paid to coach people to lift them up, help them be successful. It's a it's a wonderful system.

Jeff Perry: 59:26

Yeah, like one of the most satisfying things I have now is just seeing people, you know, people that I started at Carta with that were in entry-level roles at the time and now are like leading large organizations and have a major, major impact on the current and future of the company. How rewarding is that to watch the progression that happens. And then that's the business side. You also get to see these people get married, have kids, like have other adversity in life, and you deal with all those things together. And so, for the amount of time and effort that we we give to the workplace and what we do together, you also can't help but like become connected to people and understand that like there's more. To all of it than just like the work aspect to it.

Rajiv Parikh: 1:00:02

Well, Jeff, that's an amazing perspective. Thank you so much for spending your time with me today and sharing with our listeners uh your experience and what what you guys have accomplished at Carta and many stops along the way. It was so much fun to learn about you and your life and really what makes what builds great success and what builds great growth. There's always challenges, but there's that way of getting through it. And I appreciate your time today for that.

Jeff Perry: 1:00:24

Vajdeev, thank you so much for having me. I had a great time with you as well. Really enjoyed it and appreciate you uh having me on the show.

Rajiv Parikh: 1:00:35

That was a really great episode. You have a proven winner like Jeff, who was walking through this really amazing background where life came full circle to him from delivering stock certificates to delivering options electronically and everything in between. I think what Jeff has smartly done in his life is focus on network-oriented businesses and put himself out there in tough situations, but he's also patient in how he gets to where he is. A lot of what he does comes out of his experience playing sports and being a pitcher, being on the mound, having everyone watching you, delivering in key moments, but also knowing that once that ball leaves his hand, that's when anything can happen. And it is really about the team and it's about the next pitch, and it's about how you adjust. And you can sense that. He's in a company with many different business lines, but coming from a core capability that now keeps expanding. And I appreciate his insight about his CEO and what situations work, his drive about what got him into technology and what he thinks about when it comes to leadership. And you can sense that humility, that sense of purpose, that drive, and that care for the people on his team, his peers, as well as all the people around him. So it was a really amazing episode, at least for me. I learned a lot. So I hope you did as well. So thanks for listening. If you enjoyed this pod, please take a moment to rate it and comment. You can find us on Apple, Spotify, and YouTube, and everywhere podcasts can be found. This show is produced by Anand Shah and edited by Laura Balant. They do a fantastic job at this. I'm your host, Rajiv Parit from Position Squared. We're a leading growth marketing company based in Silicon Valley. Come visit us at position2.com. This has been an F Funny production, and we'll catch you next time. And remember, folks, be ever curious.