Coach2Scale: How Modern Leaders Build A Coaching Culture

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Matt Benelli: Alright, hello everybody. I'm excited to have the conversation with today's guest. He's a good friend with a wealth of experience and just an all around top quality human being. He's got the unique perspective of building and leading sales organizations. with some of the best brands in the technology universe.

Names like Oracle, like DocuSign, and he's currently the CRO at [00:01:00] Carta. Jeff Perry, hello. Welcome to the show.

Jeff Perry: Matt, it's great to see you again. Thanks for having me.

Matt Benelli: Great to have a conversation with you. We've had many, many over the years. Uh, this one's a little bit different. So, excited to do it publicly in front of, uh, in front of all of our closest friends. Um, Jeff, the cool thing about the show is I get to speak to people like you who are in the arena doing it every day and have done it for a long time.

Um, you've made mistakes. You're, you're human. Um, but you've not only lived to tell about those mistakes, but you're willing to share them with, uh, your leadership team, with, with me on this podcast, and with others. You're, you're a mentor to, to many. So, let me jump right into it and toss a question over to you.

And it's really... We'll call it a myth buster type question. So Jeff, what's a common myth about coaching salespeople, [00:02:00] sales leaders, that you believe is a little bit misguided?

Jeff Perry: Interesting. Tough one to get started, Matt.

Matt Benelli: Ah, come on, that's a softball. It's supposed to be a

Jeff Perry: couple of things come to mind. I think, you know, there's the sort of natural thought that, um, all, all sales people are, uh, financially and monetarily driven, and I think the more you work with people, uh, and the more you understand what motivates them, and I'm sure we'll get into a bit more of this through the discussion, but, uh, I think there's a lot more behind the scenes that.

Um, salespeople actually care about than just the actual paycheck itself. So, uh, from a salesperson perspective, that's what I think about. From a leadership perspective, two things really come to mind. Um, the first being, uh, and I, you know, I've experienced this through my career path, but, um, sort of the notion that if you're a big company person, That you can't be a successful leader in a smaller company, uh, or a startup company.

Uh, and I just, I have found that to not be true. And I think it more, uh, depends on the individual and the ingredients that they [00:03:00] have and the experiences they have and the drive and motivation that they have to be successful in a different type of role. Um, so there's, there's that, um, as far as, um, big company versus small company.

And then I also, um, you know, another thing I may or may not have been accused of along the way is that a nice guy or a nice woman can't be a great leader. And I've also found that to be false along the way. I think that, um, you can be a good person. You can be a nice person. You can also be tough and challenging and, uh, direct.

in moments that you need to be, uh, while also kind of commanding the respect of the team and the people that you work with. And I find that people actually appreciate both sides of that.

Matt Benelli: You know, um, I'm, I'm reaching for notes from a recent podcast that I recorded that touched on one of the topics, that last topic you just talked about, about being a, a, a, a nice person. Um, and you can't be a leader. Let me, let's table that for a second. The first one you talked about was, uh, in [00:04:00] terms of if you're a big company leader, And very successful at that.

You can't join a startup or a company in its more embryonic stages, right? That's, did I hear you say that right?

Jeff Perry: Yeah, definitely. And this is something that I experienced back in 2015. Uh, you know, I had a great run at Oracle, uh, part of that time working with you and I wouldn't trade that time or experience for anything. I was

Matt Benelli: Well, the time with me probably, right?

Jeff Perry: Well, that I might, I might table a little bit.

Matt Benelli: I don't blame you. Yeah. But yeah, so you got painted. Yeah, joking, but you, and I'm glad you brought it up, but you, you, you, like many others, uh, that did what we did way back when, and with a big successful company, you got painted into a box because you, not, you were very successful there, but you were there for a long time.

And I think that's where you're, you're going with it.

Jeff Perry: definitely. Yeah. And I can remember a couple of conversations distinctly with very prominent recruiters that had, uh, very interesting roles open at the time. And I really had a [00:05:00] challenge in getting them to put me in front of CEOs at that time to be a sales leader, because I was painted as a vice president at Oracle, big company, beat up on the desk.

The team tells me at the end of the quarter how we did, and I just always felt like. That's not how I operated. That's not how people like you taught me to operate. And I just needed a chance to have someone give me the opportunity to prove otherwise. And, uh, I was really fortunate, uh, you know, after a series of different interviews and I met Lauren Al Hadif at DocuSign, uh, who became a friend and a colleague and a mentor in many ways, and gave me an opportunity to prove myself as not just a big company guy.

And could I do something, uh, really productive and make an impact and help scale a company that was smaller at that time. Amen. You know, that led me to the opportunity at DocuSign, which four years after that led me an opportunity to start even earlier at a much smaller company at the time in Carta. So, um, I like to think that I helped sort of prove that myth wrong to answer your original question, but that's also not the case or what the path will be for everyone.

It just happened to be the path [00:06:00] for me.

Matt Benelli: So is there a question? So now you are the person that's looking at leaders that want to come work with you that have a different depth and breadth of experience. You know, some are, you know, may be exactly what the opportunity presents itself at Carta. Like they've done something exactly like that, but some of them might be coming from one of the larger companies that's out there.

If you. Um, kind of, um, hone in on someone that you like as a sales leader candidate, um, in, you know, that came from that big company experience and you're a little bit concerned. What's a question or two, like, what are you looking at to, to ferret out, to make sure that they don't fall into the, Hey, I was just a cog in the wheel at this machine.

And they're not going to be able to. You know, do what you need them to do at a smaller company that has different challenges than a company like Oracle or Salesforce or [00:07:00] Adobe.

Jeff Perry: Yeah, it's a, it's really timely. I actually spoke with a former colleague of ours last week, who's going through this challenge now, and she was asking for some advice. And I really think there's two main areas. Number one is. Of course network helps and relationships help. So some where someone where you have proven track record of how you work and how you operate.

Then can me or the hiring manager translate those skills and say they're transferable to what I think we would need in a smaller company. And do I believe in you as a person and a leader to be able to make that jump? Uh, and then the, and if, so if you don't have the network to help you with that first opportunity, then you're going to have to do it by telling your story of what you contribute and how you contribute it.

And that more is to the question of like the questions that you might ask in that, Matt, and I would probably ask that individual. Things like, give me an example of when you handled a situation like X, or how you thought about scaling a team. I don't care if it's in a big company, just demonstrate that how you think about how to handle some [00:08:00] of these challenges as you'll go through those in a big or small

Matt Benelli: Yeah. And I love what you said. Tell me about a time when you handled this situation. And look, it might not be apples to apples, but you're basically asking. Um, you know, a classic interview question, uh, you know, tell me when you've done, where you've done something like this before. And then, I'm smart, or you're smart enough to extrapolate whether that is transferable to what you're doing at CARTA, right?

You know,

Jeff Perry: I think so, and yeah, one of the big, uh, sort of, you know, get over the hump moves for me and when I was interviewing back in that 2015 time period was like, I'm done trying to pretend who I'm not. So I'm going to lean into who I am and what I do know and what my experiences are. And I'm going to tell that story instead.

And if that means the recruiter or the hiring manager doesn't like me, or doesn't think highly of me, then I might miss out on some of those opportunities, but I'll do a better job of telling the story of What and how I think [00:09:00] I can contribute instead.

track was, how I explain my experiences, how I work through different situations as a manager and a leader, that I could help translate that to whatever that new company might be.

Matt Benelli: And, and so that, that's about you not, you know, trying to bullsh, you know, BS somebody in the interview. And as the interviewer, you need to be able to ferret through who's BSing you or not, right? So like when you say, tell me about a time you did this, like those are the types of interview questions that allow you to do that.

But, you know, you've also said basically, Hey, look, I, you're comfortable in your own skin. You've had a tremendous amount of success at all different types of companies. And you talked about, like, look, you, you are, uh, the, you're, you're, I said it in the top of the call, like, just a great person. And you are, and I mean that with all sincerity, and anyone who knows you.[00:10:00]

Would say that and has said that about you. So it really goes toward that. What type of leader are you? Are you put in this box of you're a good person, compassionate leader, or are you a results driven leader? And, and I think the point is you can be both. And, right, I mean, would you agree with that? I mean, just because you're a compassionate, empathetic leader doesn't mean you're not results driven.

How would you

Jeff Perry: I appreciate it. But I also think that, uh, yeah, I think you can be both. And I think, like I said in the beginning here, Uh, people appreciate working with or working for people that are genuine. And I think you can be a compassionate, empathetic leader while also being firm, uh, and demanding and, uh, and, and build relationships with people that create trust over time that allow you to ask for the little bit extra.

The, I know you talk a lot about the 212 degrees and the boiling point. Like you don't get to ask for that extra effort if you [00:11:00] haven't earned that trust with people. And I think you can do that by being. Human and genuine, and you can also be firm and direct as needed. Uh, and I've found that over time, like that's, that's the recipe that's worked for me and it's, it's worked even more because I haven't really had to change who I am, I think that's, that's the genuine part of me and I enjoy the work I do with people, I enjoy the people part of the business, I enjoy the results part of it as well.

I, as you know, I was a baseball player in college. Like I'm competitive. I want to win also. Uh, but I see both sides of the business, the people part and the results part. Uh, pitcher, unfortunately.

Matt Benelli: Third base, right?

Jeff Perry: You usually call, you usually call me the catcher, but yeah, thank you.

Matt Benelli: Busted him there. Well, uh, so, uh, interesting storyline there. Might as well tee it up. who is that kind, kind of famous Boston guy that, that also, um, went to, went to college with you?

And he was a little bit behind you,

Jeff Perry: is, uh,

there is a guy

named

Matt Benelli: you know

Jeff Perry: who was a couple grades [00:12:00] behind me when I was at Sarah High School and he was a really good baseball player at the time. Turns out he made the right choice and took the football path and, uh, that worked out pretty well.

Matt Benelli: Yeah, so, Brady, I think he was drafted by...

Jeff Perry: he was, correct. Yeah. Montreal

Matt Benelli: Was he drafted by the expos

Jeff Perry: round it was. I think it was an early teens round, but, uh, not a bad choice. Six foot four left handed hitting catcher with a gun for a right handed arm. So, uh, he probably would have had a great path in Major League Baseball. In fact, I've talked to our former coaches about that who believe.

He would have made it in either sport. So

Matt Benelli: yeah. Um, crazy, crazy stuff. So you, you've always talked about the importance of culture, of team, of bringing, you know, uh, the right mix of people together. When you think about fostering that type of culture, you know, even a, you know, sales culture or [00:13:00] coaching

Jeff Perry: it's interesting cause it kind of ties to the question you asked before. Like, you know, I think most people would probably consider me a locker room type guy, given that you played a college sport and, you know, you would only associate yourself with males that are same age bracket as you, similar experiences and actually what I found once I got out of, uh, you know, the college and, and, and sports experience when I got into the business world.

What I realized is the importance of diversity and creating more diverse teams. And it's one of the things I'm most proud of now is the opportunities that we've created for. All different people, different genders, different ethnicities and opportunities and leadership roles. Uh, and I couldn't be more proud of the work we did at Oracle and changing the profile and the landscape of what a diverse team looks like.

Uh, I got to do that even again and further at, at, uh, DocuSign and couldn't be more proud of the team that we've built and the opportunities that we've created for men and women, uh, inside of Carta as well.

Matt Benelli: [00:14:00] Yeah, no, really good to hear you say that. A lot of work was done, um, way back when, uh, at Oracle. And I think, in my perspective, you've always been at the, at the forefront of that and working with you at Oracle and then, um, uh, you know, Docu, with you and Lauren. DocuSign was a client of ours. Uh, Carta is a client of ours.

And I can honestly say it's, it's always been. Uh, one of the more, uh, diverse, uh, teams in, in the sales business that, as you know,

Jeff Perry: Well, our industry, like Fin,

yeah, FinTech sales,

like we're prone to that. But I really think, uh, the work we did at Oracle changed my frame of reference and what the profile of an ideal team should look like. And then there's really like two driving motivators, I think as well. Like I have a working wife at home that has built a career and she's able to balance like being a mom and having a full, very heavy workload as well.

And then the second part is like, I have a daughter who's in college right now, and I want her to feel like. She has an [00:15:00] opportunity when she graduates from college to go be part of, if she wants, a sales organization that provides all the opportunities that it would for anyone else that she potentially graduates with or grew up with, too.

Matt Benelli: yeah, uh, amen, amen to that. Um, so back to the, the business and talking, let's go, I want, I want to talk about a this or that question. And so it, it. It's, it's, there's no, it's not, it's not an easy answer, but there's no right or wrong answer. Uh, just going to throw it out there and hear your reaction. So Jeff, if you're a frontline manager, is it better to finish the year at 130 percent of plan, but only a third of your team makes their number, or is it better to finish a little bit lower?

Let's call it [00:16:00] 115 percent, but everybody on the team exceeds plan by a little

Jeff Perry: Well, can we have it be 130 percent and everyone achieves, too?

Matt Benelli: What do you think?

Jeff Perry: Well, that would

Matt Benelli: That's

up to you, but that's a good answer. That's a good point. Uh, but

Jeff Perry: sure, we have these peaks and valleys throughout the year and, you know, we're a monthly business and part of our business and other parts of it are quarterly. But what you really want to see is balanced, positive productivity and contribution.

Uh, and you want to see that across the organization. And so yes, exceeding the target, if it's 130%, whatever the number is, that's of course what you want. But if it was 127 percent and you felt like you had much better contribution and you were learning and people in your organization were growing and developing as a result of it, that's a far better place to have the health of the organization to be in.

Matt Benelli: so if we could pull that thread a little bit more, what good things happen? When [00:17:00] everybody's performing on that team versus when only that special few are and other people are

Jeff Perry: Yeah, well, it actually,

Matt Benelli: they're, they're

Jeff Perry: ironically, it creates what is an actual team because people are pulling for each other and supporting each other versus finger pointing of what's not working for them or why someone's getting more or better leads or so. And so you remember this has the better territory. Uh, we dealt with that for many years.

And so when you have more balanced productivity and contribution, people are more inclined to be helpful and supportive of each other. And that means they're learning from each other that creates a much better and healthier organization.

Matt Benelli: And so when you think about what you've picked up along the way, leading these, uh, just marquee sales organizations, do you have a recipe, a playbook, a framework for building this culture, for building this

Jeff Perry: Yeah, I do. And I don't know that it's the right one, Matt, but it's, it's what I've tried to do since, uh, you know, I think [00:18:00] back in 2006 or seven, someone had the confidence in me or that saw the potential ingredients to say he's maybe not. Uh, the perfect resume right now, but we believe in him potentially being a manager and that led me down a path that I never even knew was a potential path for me.

Uh, and so to me it became like, how do I do this for other people? And how do I create a culture of people like trusting you and feeling like they're part of something that they're not just a number. And their leader cares about them as an employee, but also as an individual. And so I just try and, like I said earlier, be genuine and get to know people.

That gets much more difficult when organizations get much larger, obviously you can't know everyone and go as deep with everyone, but I try and make an effort to make sure that I'm connected with people, that I'm interacting with them. In some cases, probably far too much in the weeds, but that's my way of staying close to the business and close to the people.

It also shows people that like, I care about what they're doing day to day. In fact, I was at the Sastr conference that we [00:19:00] sponsored last week. And I had, I can't tell you how many people asked me like. You're the CRO. Why are you, why are you working at the booth? And I, I can't believe the question. I loved every minute of it.

Like I was learning from customers. I was learning from prospects. I was staying in tune and in touch with what's happening and relevant in the industry. And maybe most importantly, I spent time with nine of my other team members. And got to know them better and showed them that, like, I'm in the trenches with them, and I'm going to help them try and find and generate as much top of the funnel as we possibly can together.

Matt Benelli: Yeah. Well, leading by example. Uh, you know, kudos, kudos to you. Let's, uh, let's talk about deals for a second. I know we've, we've talked about a lot of deals, um, over the time in different capacities, but when I work, uh, with leaders these days, uh, especially when I work with frontline managers, It's a lot about the, the deal.

And [00:20:00] when I talk to individual contributors, they say, all manager ever really cares about is, you know, the number is the deal. And we know that's not the only thing, but it's very important, but frontline managers can over index, right? They could focus too much on that at the expense of other important parts of the business, other important parts about the development of the individual.

What advice do you give? To those frontline managers who focus perhaps a little

Jeff Perry: Yeah, it's hard because you do

have to focus on the deal, right? We're here to hit a number, and the only way you hit the number is by executing against those deals. Uh, one of the things I like to talk about and think about with the group is, is not just that deal, but how did we find the deal so we understand how we can go find more and can we replicate it?

And then the other part to it is, I always ask, like, Who else have you included in the deal? Because I think it might've been you that taught me this a long time ago. Like don't ever lose a deal alone and make sure that you've involved the right people. Cause you don't have to have all the answers and.

If you're going to have an opportunity [00:21:00] to win it, you might as well have the best people around you as part of your company or part of your team to help you win the deal versus trying to be the rep hero and win the deal on their own. That usually doesn't work out well. And I think, you know, we've got hundreds of examples of this over time where the best deals that we've seen closed involve a great team of resources and SCs or product people.

Uh, oftentimes there's marketing support as well. It truly becomes the team effort. And I actually find that the AEs that are able to sort of release the ego part of like not having to be the sole focus of the deal, actually are the ones that have better success overall.

Matt Benelli: Yeah, so never lose a deal alone. I mean, especially in this environment where it's increasingly becoming a team sell and companies invest in the resources to support the team sell. If you're losing a deal alone, you're doing something wrong, right? No lone rangers. Um, because [00:22:00] we don't want people to win the deal alone, right?

It's when you win, it's a who else helped you. But when you, when you lost, hey, what can we all learn, right? There's the, there's the benefit of different points of view and having not just a team that's diverse in terms of their ethnicity or their agenda, but diverse in terms of their experiences and their thoughts,

Jeff Perry: Totally agree with it.

And I think

it's

Matt Benelli: right. Would you agree with that?

Jeff Perry: far more than any other time in my career now that it has at Carta. Like, I can't tell you how many deals Henry, our CEO, Henry Ward and Charlie Keevers, our CFO, are involved in. That could be like me saying, are we not good enough to get things closed without their help?

I see it as the opposite. I'd rather include them because they're experts in these areas. I mean, Henry is brilliant and he's visionary. Uh, people want to hear from him and understand the future of fund admin and cap table management and equity management and creating equity for all. Why not have that [00:23:00] person in the room helping you close deals too?

Matt Benelli: Yeah. And, and, and so when, when you think about like having them close deals for you, right, or, or not for you, um, but with you, you're getting their perspective and, you know, people like Henry and Charlie, they're, they're brilliant. They're successful. They've been doing this. They've seen a lot. And so again, it goes into that diversity of thought and experience.

Uh, one of our podcast guests, uh, Bill, Bagshaw, it actually dropped today, um, talked about the important, what actually, what he talks about was the best people that he's coached in the past over his many years as a sales leader. The best people were the ones who soundboarded with the most other, with most people.

They brought their manager and they brought as many people as possible that could come in and provide [00:24:00] perspective. And it sounds like you're supporting that. Also, in terms of just getting, you know, uh, people, different perspectives involved in looking at the deal, trying to solve the problem at hand

Jeff Perry: 100%. Like, I love

when AEs come to me or, you know, send me a slack and say, I saw you were connected to so and so. Would you mind sending an email to a customer? Or, I saw they were connected with Charlie or Henry. Can we triangulate in those ways? Like, I love that you're thinking of all different ways to make sure that we've done everything possible to win as a team versus just trying to send a contract and hope that it gets signed.

Matt Benelli: Okay, so let's, again, let's talk through this just a little bit. And here's why. Jeff, the reason why we have this podcast is, uh, not just to hear, uh, ourselves talk, but it's to share experiences, to share ideas, to share tips, to debunk myths with people that are coming up behind us, uh, cause they struggled with the same type of stuff.

We did, and there's [00:25:00] a lot of individual contributors that are going to listen to this, a lot of AEs and AMs and, and SDRs. There's, there's a lot of frontline or newer managers, newer leaders at every level that are going to listen to this. So I want to, I just want to make sure I heard you right. If, as the CRO of an organization, if, if somebody comes up to you, if a manager.

Or a rep comes and sees you in the hallway or, you know, they see you on Slack or whatever it is, and they say, Hey Jeff, I saw on LinkedIn that you're connected with Brendan Kalika, Dane Saleh, or XYZ person. Can you reach out to them and, you know, tee up a conversation? Or do you have any advice? I have this call coming up with them.

That's not a sign of weakness to you, but that's actually a sign of strength. And you want, you

Jeff Perry: in fact, I would take it a step further and question if you're not doing those things, why aren't you?

Matt Benelli: [00:26:00] Alright. Um, so in terms of coaching and leading, uh, do, how does it change, if at all, in different market conditions? Because we're in a different market conditions. A lot, a lot of people would say right now, we, you know, you know, the peaks are as high as the valleys are low, but how would you, how would you address that?

How, how does it

Jeff Perry: Yeah, well, I think it

changes drastically, and we've experienced that, especially over the last three years. We were at the high, and then the COVID low, and then immediately spike back up, and then to moderation, and then market conditions. So, we've seen the roller coaster, especially over the last three years.

Um, and to me, the, the role of the sales leader or sales manager in that, Is being even keeled, right? Because part of the job is becoming the psychiatrist of keeping people focused and energized about the good things that are happening and the impact that they can make and controlling what they can control within their territory or their customer or their pipeline, [00:27:00] because the other stuff you can't really do anything about.

And so if you waste time and energy and mental spend on that, you're not helping yourself move forward in a positive way. So I try and be, and I try and lead by example in that way. I think, you know, I probably. Look back on it as my experience, you know, playing baseball and being a pitcher. Like I had some good games, I had some really bad games and like, you try and make sure that like at the good times you're staying at a level pace and when things get tough, you also stay at a level pace.

And I think people appreciate, um, that consistency and that transparency. And everything I learned from a baseball field translates directly to business experience as well.

Matt Benelli: Thank you. Um, so let's talk, let's pivot a little bit and talk a little bit more about you, Jeff Perry, and, and your career journey. Um, you're at Carta now, um, what is Carta's business and what's motivated [00:28:00] you to stay with Carta

Jeff Perry: Yeah, so Carta, uh, started as eShares and became Carta, um, with the mission of creating equity and ownership for all. And to me, I probably didn't realize the impact of that when I accepted the role and first started at Carta, but it's grown on me over time and did quickly, uh, when you start to realize the impact that Carta can make on millions of people worldwide and helping them have equity.

in a company that they're working for either as an employee or as an investor of some kind. Uh, and it's for every role. And so that's created ownership for people in an SDR role or in the CEO role. And to me, that's a wonderful thing. And we're creating opportunities for people, uh, to, to make sure that like they benefit from the impact that they're making at a company.

Um, and that's helped me, uh, want to stay as sort of the driving factor. There's other things inside of that, Matt, like. You start to realize, um, Carta is a complicated company and we started [00:29:00] as a cap table business and we are managing cap tables for companies and we're distributing equity to the stakeholders of either employees or investors typically.

Um, we have then since expanded, which is something that I think is really cool. This was not even talked about when I first met Henry five and a half years ago. But now we've taken all the compensation data that we have from the cap tables, and we've created a compensation benchmarking tool. Talk about a really cool product, right?

Now we can say that if you're going to take a role at a, at typically a tech company, a venture backed company, we can tell that company exactly what the market rate should be for that specific role, both cash comp and equity. So talk about people being paid fairly based on gender. That is irrelevant if you're following the CARTA guidelines of the compensation benchmarks that we now have produced based off of 35, 000 plus private venture backed companies, which is real time data.

We've also taken, like, tax advisory and made that a product. If you think about [00:30:00] all, you know, younger people starting their career and getting equity and what it, what the implications are when You accept the grant as it vests, if you exercise in the event that you're lucky enough to have liquidity around it, what are the tax implications?

We have a product that companies can buy and offer as a benefit. We have a whole separate business that is the venture capital space, which is software and services for back office fund administration. For some of the largest VC firms in the world, we have over 1, 800 Funds on our platform. Now, we've created a whole bunch of other products around that servicing the VC needs as well.

A mobile app called Carda Carry.

Matt Benelli: Yeah.

Jeff Perry: Probably three or four years ago, we were getting hundreds of inbound leads from LLCs. And so. LLCs would start to use the Carta cap table product that was typically designed for a venture backed C Corp type company. What we realized is many of these LLCs came to Carta because they had a similar ownership problem track ownership tracking problem that [00:31:00] they could now do in Carta.

So we've created a whole new product. To help service LLCs and how they track ownership that opens up a whole new market for us that could be far bigger than what the venture backed C Corp, uh, market is as well. So what I love is like, we're always thinking and, and, and engineering about what the next thing is to help build the next product line.

Matt Benelli: Right. And, and if you're an, if you're a, uh, an individual

Jeff Perry: I can't tell you

how many people in my

organization have worked in. One, two, or three of those roles that I just mentioned to you because it creates a ton of different career opportunities. And if you think about it, how much more marketable does that employee become X years down the road when they can say, I've had experience in working with cap table, FinTech software sales.

I've worked with venture capital firms. I've worked with private equity LLCs. You just opened up a whole new universe for yourself as far as opportunities.

Matt Benelli: [00:32:00] Well, I can, I can, uh, I can vouch for that. We are a, a Carta client. Um, and so, yeah, so thank thank, thanks for that. Can we get a beggar discount? No. Okay. Alright. Um, so we we're talking about coaching and we've been talking about that for. You know, about a half hour now, um, and you, you know, you've talked about baseball, like we've weaved a lot of stuff in there.

Usually people that demonstrate, you know, great leadership skills and coaching skills benefited from that themselves. It's not just the type of thing you can learn in a training. Um, there's a lot of things you can learn in the training, but really it's like, what was modeled to you? Can you tell us about a time, Jeff, where you benefited from really good coaching and

Jeff Perry: Uh, okay. So since you said I can

go

anywhere

I'd actually take it even a step further. It's like real life coaching that I gained and I was fortunate to gain from my parents. I think when growing up and you know, I can remember [00:33:00] moments, my dad, like talking about how he treated or interacted with many of his employees and he worked for a laundry business.

Um, and so totally different industry than I am. It doesn't change the fact that you're working with people and that's how you treat people. And I think I learned that from him early on. And then you go through like playing baseball at a fairly high level and you know, great high school coaches and childhood coaches, and then get to Santa Clara and you had like incredible baseball coaches that taught you not just about, you know, baseball and the fundamentals, but also about like life and the importance of showing up and being diligent and meticulous around details and all those things that I mentioned translate to.

To business opportunities. And then you get to actual business and you have incredible role models that you like, I'm visual learner. So I learned from watching the leaders that I respected along the way. And I tried to kind of take the best of what I saw in their styles and sort of mold that into my own.

And I also tie that out back to like my baseball [00:34:00] days. Like I knew I wanted to be a pitcher. I knew I couldn't throw as hard as Nolan Ryan, but I loved watching him and I learned from that. And then I said, well, Greg Maddux actually. is a little more in the range of my speed. I'm going to watch how he pitches and moves the ball and offsets timing and things like that.

Those are, that's how I learned. And I took the same principles into business. And I learned from Dan Freund and you and Rudy Corsi and Keith Kroc and people at DocuSign, Neil Hudspeth. And, you know, I've had, I've been fortunate to have great leaders along the way that I've been able to, Uh, to try and emulate and, uh, you know, try and almost pay it forward as well.

Like back in the day, David Baga and James Volpentheft were the guys that first gave me an opportunity to become a manager, which I might not even have been deserving of that role. But I look at it as now I get the opportunity to, to invest in people like they did for me, uh, and, and help build whatever their career path becomes down the road. And I

missed

some, I apologize,

Matt Benelli: a little [00:35:00] walk down memory lane too. So I, Oh, yeah. No, listen, that's, uh, that's always the, the downside of, of bringing up names, but, uh, you, you're, you know, very inclusive there, a lot of great people. Um, and, uh, actually hope some, you know, some of them, I'd like to see if we can get them on, on the show here.

Maybe you can help with that. Um, but listen, Jeff, uh, honestly learned a ton today and appreciate you sharing that with us, right? Everything from the importance of not abandoning who you are as a leader. Thank you. But, but leaning into it, right? You, you can be a compassionate, uh, empathetic leader, but also a results driven leader.

Uh, just because you got, worked at a big company, or worked at a small, smaller company, doesn't mean you can't cross the chasm and take your skills and apply them in a different type of role. Right? So you debunked a couple of myths there, um, on the show, but you've also debunked those myths. personally, right?

You've done it. [00:36:00] So, um, really appreciate you, you doing that. Um, any final thoughts for the audience? And if you think about the audience, it's people that, you know, work, like the type of people that work, uh, for you and with you at CARTA, right? Um, but, you know, just broadly speaking.

Jeff Perry: Yeah, well, uh, thank you for the kind words, and I feel like hopefully the things I've debunked, uh, that's helped me. Hopefully it helps pave a path for other people down the road too, and hopefully it paves a path for my colleagues here at CARTA, because I feel like... We have an incredible opportunity with what we have built to this point.

And it really does feel like we're just getting started on what the opportunity can be down the road. Uh, because we have all these different products and different business lines that we're in, and that's going to create career opportunities for people that they don't, might not even know about in a couple of years.

Right. And, um, my, my, my ask, my wish, my challenge of myself is like. Cause we're lucky. [00:37:00] Like there are people that spend 40, 50 years working and they do a great job and maybe work for a mediocre company. And it's a job. I don't feel like we have jobs. I feel like we have great opportunities in front of us.

And we work with great people. It's up to us to go maximize that opportunity that's there in front of us. Now,

Matt Benelli: Well, I'm happy that we're a Carta customer. Um, I'm happy that Carta is a client of ours and, and have the opportunity to work with such great people. Um, really, really appreciate that. so, Jeff, a lot of people heard the depth and breadth of Carta. They're hearing about the culture that you're building. If they want to be a client, or if perhaps they're interested

Jeff Perry: thank you, Matt. Uh,

please find me on LinkedIn. I'm Jeff Perry. I'm the CRO of Carta. You can go to carta. com and go into our chat bot. Um, you can, you can email me jeff. perry at carta. com. I'm always happy to connect. I [00:38:00] do think. I'll be happy to connect with founders and funders as those are who we help support as customers, uh, but also people that might have an interest in, in, uh, working at Carta at some point, we will continue to be growing.

And like I said, we have all these different opportunities to create different business lines. So, uh, look forward to connecting with, with your audience soon, Matt.

Matt Benelli: Alright, we're gonna leave it right there. Jeff really enjoyed the conversation today.

And thanks to all of you out there for listening. If you've learned something today, if you laughed a little bit, tell someone about the podcast, Coach to Scale. C O A C H, the number two scale. Again, Jeff, thank you. It's been my pleasure to host this conversation on behalf of Coach to Scale. And until the next time, coach them if you want to keep them.

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