Ep. 113 – From CRO to CEO: What Boards Really Look for in Sales Leaders with Jason Baumgarten - Part 2
Ep. 113 – From CRO to CEO: What Boards Really Look for in Sales Leaders with Jason Baumgarten - Part 2  
Podcast: Selling the Cloud
Published On: Tue Feb 10 2026
Description: In Part 2 of this Selling the Cloud conversation, Mark Petruzzi and KK Anderson continue their discussion with Jason Baumgarten, diving deeper into how boards think, govern, and evaluate senior sales leaders once they reach the highest levels of leadership.Jason unpacks why boards care less about confidence and more about clarity, learning, and diagnosis. He explains how CROs must evolve from operators into enterprise leaders who understand risk, governance, succession planning, and investor expectations.The conversation also explores what executive vetting really looks like at the senior level, how boards assess integrity and credibility over time, and why understanding context behind results matters more than headline numbers. This episode is essential listening for CROs, CEOs, and revenue leaders aspiring to board seats or the CEO role.What You’ll Learn:Board Governance for CROs: Why sales leaders must understand how boards think and operateInvestor Empathy: How understanding investor pressure builds trust and credibilityLearning Over Bravado: Why boards care more about why results happened than confidence aloneRisk Awareness: How governance thinking changes how CROs evaluate decisions and tradeoffsSuccession Planning: Why boards expect leaders to plan for a future beyond themselvesBoard Readiness: What boards actually look for when recruiting sales leaders as directorsExecutive Vetting Reality: What senior leadership evaluation really includesIntegrity Signals: Why honesty about misses builds long-term executive trustKey Topics:Board governance through a sales leadership lensOperator mindset vs investor mindsetRisk management and risk of inactionStakeholder alignment beyond compensation plansSuccession planning and leadership maturityBoard selection criteria for sales leadersExecutive search and forensic referencingEthics, credibility, and long-term reputationContextualizing revenue performance and growthPreparing for CEO and board-level rolesGuest Spotlight: Jason BaumgartenJason Baumgarten is the Global Head of the CEO and Board Practice at Spencer Stuart, where he advises boards, investors, and executive teams on leadership selection, succession planning, and governance. He has led more than 250 CEO and board transitions and brings deep expertise in evaluating executive readiness, integrity, and long-term leadership impact.Resources & Mentions:Spencer StuartHarvard Business Review: How CEOs Build Confidence in Their LeadershipBoard governance and executive succession best practices🎧 Listen now and follow Selling the Cloud for deeper conversations on executive leadership, governance, and what it truly takes to move from CRO to CEO.KK Anderson (00:31)Let's talk about board governance for sales leaders. Jason, sales leaders are, as we've talked about, they're heads down. They're working on pipeline. They're working on deals. But investor expectations are ultimately what shape the pressure that's behind the number and behind the quarter. so talk to us about why.should sales leaders care about board governance? What changes when they start thinking like the investors instead of thinking just as operators?Jason Baumgarten (00:56)So it's hard. I don't have a perfect one size fits all question because obviously every situation is different and every sales leader and company is in a different position. But I would say going back to this concept of empathy of the individuals, if you're an investor that has to return to your LPs, you've got a job to do. You're showing up and trying to explain how this investment is going to drive LP returns. And I think the first and foremost thing is for people to understand that individual connection that somebody showing up in your boardroom has.Like why does it matter to them? what's driving their anxiety, their pressure, their sense of, combated and this at times or, or, skepticism that you're doing good job. So that's one. think the second thing is really bringing that mindset of what have we learned, not just what have we achieved. the problem is half, I would argue frequently sales leaders when they are successful, they have no idea why.And when they are unsuccessful, they have no idea why it's like I walk into a CEO's office and they say, look, the stock price is up. And I'm like, why? It's a good rumor going around. So I think the reality is it's really important to hit your numbers. It's even more important to know why you hit your numbers, because that allows you to do it again. And when you don't hit your numbers, your board and your investors are going to be disappointed. But the critical question is, can you understand why?and articulate what you're going to do about it, even if you don't have the perfect solution, you can bring them into the problem with you and say, here's what we believe happened. Here's now what we're trying. If you have other suggestions or people that can help us unpack this, we're all ears. I think the people who often lose their boards are the ones whose confidence overpowers curiosity or humility. And they come in just sort ofclaiming that they're going to hit their numbers next time. Because the problem is, if you succeed, great. But if you miss again, you've now lost the confidence of the group. And the problem is, you don't have perfect control over your outcome, right? You could walk into a market that's falling, and you haven't figured out that it's falling yet. So what are you going to do to sort of unpack that? Now, you know, listen, at the end of the day, nobody likes to be told that the numbers aren't good. But they want to they want to understand why too, because they don't want to be surprised.if it's a bigger problem or it's a structural problem that they don't understand. And salespeople are often the tip of the spear because that customer intimacy, they understand. But for example, are you seeking out that information? Are you trying to figure out what went wrong? if you were sure you were going to close a deal and you didn't, are you really honestly asking what went wrong so that you can diagnose it? Or are you trying to explain away the miss?And I think people get caught up in the game of ⁓ performative explanation of like, let me look good explaining the miss as opposed to being genuine and saying, I put the wrong person on the deal, or I was overly optimistic and I didn't realize we actually had five competitors well positioned and I thought we had won or our pricing was a total miss, right? Whatever it is,really being honest about trying to figure that out, I think goes a long way versus trying to, use bravado or confidence to convince them that it'll just be better next time. Because if you're right, great, but you don't really build your case as an executive. Whereas when you can really bring them into what happened and what you've learned from it, what you're going to try differently, what the team's trying differently, you build an enormous amount of trust and confidence that you're on.that you know what you're doing and you're ready to tackle it again.Mark Petruzzi (04:13)So Jason, what does thinking about governance actually mean for a working CRO? How does it change how you run your organization?Jason Baumgarten (04:22)So it's a really good question and it depends on the governance of company, but I would say there's probably three things that should circle in your mindset from time to time. One is risk. Most sales leaders don't think a whole lot about risk. They think about missing a number, but they don't think about what is the risk of that? What is the broader risk? What is the risk of serving a particular customer? What's the risk of a hire? So first and foremost, it's,part of the board's role is to think about what could go wrong and how do we mitigate that. So I think when you start thinking about it with a governance lens, you do temper some of the things you might do and say, that actually could be risky. We, something bad could happen to the company if we pursue that approach. So I think that's one is just this mindset that risk matters. By the way, there's another side of that, which is the risk of inaction, right? The risk of not doing can also come back.So I think that's one. I think the second thing is that it does get you in this stakeholder mindset of beyond the incentive plan, beyond the annual comp structure, beyond the value of your equity in the secondary market right now. What is the bigger picture of what's going on here? And what am I really solving for? There was a book years ago, probably 30 years ago called How to Become a CEO. And I always remember this line from it. said,Your job is to make your boss look good and your boss's boss look even better. And, one of the things sales leaders should think about is, you know, the board isn't ideally is not there to pass judgment and be critical. They're actually there to help you be successful. There's nothing they want more. So how do you think about, your role in all of that and how it ties into the broader trajectory of what the company is trying to do again, so that you can connect those dots and you can, you can be a more holistic leader.And then I would say the third thing that board spent a lot of time thinking about, and I think is helpful for sales leaders to think about is succession planning. And the reason it's important is if you've got a lot of aspiration, you're hopefully thinking about what you want to do next. But it also helps you think a little bit more about your team and how you're developing your team. And I think boards think about that because it's one of the things that, you know, probably stresses them out more than anything is notif it's going badly, but when it's going well, that somebody is going to walk out the door or something's going to happen. And so I think showing that maturity of planning ahead and planning for, Hey, what happens when I'm not around? You know, who's gonna, who's gonna run the play.KK Anderson (06:32)Well, speaking of that next, getting to that next level, a lot of sales leaders say that they themselves aspire to sit on a board one day, And few understand how boards actually select members when they're looking to add a director and specifically one with a revenue background, right? Talk to us about what boards are looking for when they're tapping asales leader, someone with sales leadership experience to sit on that board. And then how can the sales leaders today, in succession planning, I suppose, right, but for themselves, like how can they begin to prepare and plan toward that ultimate goal of being able to sit on a board?Jason Baumgarten (07:10)Yeah. So I would say that there's a couple of things. One is there's, venture boards, there's private equity boards, there's distressed asset boards, there's public boards, a lot of different kinds of boards out there. So the first thing is, they're not all the same. And they're not all transferable skill sets. The more established the board, the more it's about governance, the more the board is, you know, maybe for a smaller company, then often the board is a little bit more aboutI would say it's the team you can't yet afford to hire, right? It's the folks that are just, you couldn't bring them on to your executive team, but you want their assistance, you want their help, and you want them rowing on your side. So the first thing is to really understand that those are all different boards or different selection processes or different approaches. Within that spectrum, I would say the smaller boards are looking at you as more the person who's a step ahead, right? Who's seen a movie they're about to go to and they want the advice and counsel.And in that case, it's really just about being a excellent near day job and be showing up knowing you don't have every answer and there's other people in the room are going to have good answers. And, you're there to be of service to the, to the management team and to the investors, typically investors, as you get more seen, you know, as you get more, to the established boards, either very large private equity, a pre IPO or a public board, it is a little bit more about governance. And then the question is, you know,The way that those boards operate is typically they've a very, very defined spec. They'll come in and say, we need a, CFO who has experience in Latin America, specifically Brazil, who has also worked in Japan and who has deep channel experience and Revrec, with Revrec and channel experience. They don't come to us and say, need a good person. Right. And soThe first thing is recognizing that just because they're seeking a board member doesn't mean it's you. The second step is figuring out, when they do need a sales leader, what are the kinds of topics they're often dealing with? And how do you best position yourself as somebody who's thoughtful, who is advancing the state of the art in sales leadership, in revenue leadership more broadly, in the industry you're in more broadly, so that people see you as an expert.a little bit beyond your current, domain or your professional experience. And then also recognize that part of the role on the board is not just to bring your expertise, but especially as you get to the bigger boards to be thoughtful about risk, ⁓ &A, succession planning, all of these other topics that boards are responsible for. Even understanding that those are the topics boards talk about. I mean, I always say to somebody says, I want to be on a board, I'm like, do you know what's on a board agenda? And they're like, no. And I'm like, well, that's a good first step, right? Like,KK Anderson (09:32)YouJason Baumgarten (09:34)And not in a bad way, but like, go to your own board and figure out, go to your board members and ask them if what they would advise, right? Do they see you as somebody who can contribute to a board, get to know your own board as a first step. I think then really thinking about the then really thinking about how do you bring that perspective because they don't, they're not interviewing you for how excellent you are at meeting a quarter orMark Petruzzi (09:34)Thank you.Jason Baumgarten (09:57)breaking into a new account because that's not your job as a board member. They're probably going to interview you about, if they're if they're contemplating in organic growth, they're going to say, great, how have you thought about the big picture integrating sales teams at scale? How have you thought about that? Or how have you thought about advising a team that's that's, you know, going through a business model transformation or a pricing transformation? They want to see that you can think at a more strategic and advisory level versusbeing a great operator. you know, and I would say, I get asked a lot about executive classes and about trainings, they will not help you get on a board. But they may help you sound like you know what a board does. And they may make you more capable if you are lucky enough to get on a board. At a minimum, find a book about boards and read it. They're usually not the most scintillating reading to warn you ahead of time, there's no blockbuster movie about governance.said to anyone ever. But there is, you know, there's some wonderful books that take you through the legal responsibilities of a board. And if you're serious about it, you should you should do that again, not because it helps you get on a board, not because anyone's going to select your resume, because you added your LinkedIn that you read the ABA manual on boards. But because when you're talking to a head of non gov or an investor, they're going to go, this person actually sounds seems to understand what we do.Mark Petruzzi (11:11)Excellent. Well, Jason, I can't finish up here without having you go a little more general on all this around, landing your next role, topic four. what really matters at the senior executive level. So, you've also said out there in some of your publications that salespeople think they can BS their way to better gigs. But at senior levels, reference inreferencing gets really intense. for those who haven't been through a significant vetting process, what changes at that next level?Jason Baumgarten (11:44)And by the way, I wish that was only sales leaders. think many, many leaders think they can talk their way through the next role. The reality is, I mean, just to give you a perspective, for a senior executive, typically a company, you know, working with us, for example, may take 20 to 25 references. They may do a four to eight hour assessment. They may do a psychological assessment on top of that.Mark Petruzzi (11:50)HaJason Baumgarten (12:07)They are typically going to do a background investigative check that doesn't just say that you had a job, but they will be sending representatives to call on every courthouse in every city you've lived in to make sure there weren't cases that were dismissed that didn't make it to the digital databases. They will screen your social media posts for inappropriate comments. They will look for any shred of evidence that you have done things that are unethical.or that will cause risk or challenge to the organization. All of that, and then there's the bevy of actual interviews. And then typically a case study or a working session, typically a few dinners or lunches or breakfast. So by the time you're done with that process, most likely they're going to find out what they're going to find out. So that's a couple things. One is how do you get a great gig be excellent at your current gig?Second, really try to build bridges along your career. And even if you don't like somebody, don't make a big deal of it because it'll come back to get you. Third, be really upfront with anyone trying to hire you about what didn't go well and why, because they're going to find out. And so it's much better to say, hey, you know what, that job that was two years, it actually was not a success. I learned a ton. Here's what I learned. I had a boss that just was oil and water. Here's what happened. Because if you try to position it asNo, no, was really successful. And I do 15 references and everyone says you were an ogre. It's not explainable because then it's an ethical lapse. It's an integrity lapse. So that would be, kind of what the process looks like. Now, there are plenty of roles where it's, I called a buddy and the buddy vouched for me and I got the job. And, you that's awesome. That still happens. But at the more senior levels, I would say, generally speaking,expect that level of scrutiny and process. Certainly for a CO role, if not a CROKK Anderson (13:47)Wow.Yeah, that sounds exhausting.Jason Baumgarten (13:51)Yeah. And by the way, even customers, I have had numerous examples in the last decade plus where somebody says, I built the so-and-so account. Well, guess what? If that CEO is a good friend, which chances are we know them or our clients know them, we're going to call on them. If you're not working right now, we're going to just ask them flat out what the story was. But if you're working,One of the most powerful reference questions is, hey, Mark, you get called on by a lot of salespeople, a lot of software companies. Who do you make time for?Boy, don't make, I now know you didn't mention Johnny, but Johnny's told me he's your best friend. So now I'm saying, well, Mark, you sounds like you've done a lot with these four or five companies. Is that true? No, you don't mention Johnny's company again, strike two, strike three. Well, I know you're not mentioning, XYZ company, but what about Johnny, Chris and Mary? You seem to know them all on LinkedIn. they people you really, I don't even know who that person is.Well, now you've lost me at the company knows me. I'm important to the company and I actually have personal relationship and don't underestimate those calls that will happen, particularly investors. They will do forensic referencing where they'll take that. They'll go through your resume and look for every connection you've ever every client you've listed, every connection, everything you've done. And then the other is probably goes without saying, but the other Holy Grail is just never, ever, ever mistake.published document, I mean, in any format, but particularly anything that is, you where you're really putting your name to that, that you did that, whether it's a degree, a job title, we've, found this recently, where people are being a little loose and fast with job titles, just stick to the facts. You don't need to elaborate. Don't put a, don't put a, P and L leader, if you weren't one, don't put a general manager, if you're really not one, don't elaborate becauseYou may not be thinking about it now, but in 10, 15 years, that'll catch up to you. We had an executive years ago who overstated something probably 20 years at a company, but in his official biography with the company, he had overstated something and he didn't even remember doing it. It was when he was like, you know, in his twenties and years and years later, he went to switch roles in a very, very senior role and this became a real issue for him andhis entire career almost unraveled because of this thing he did 30 years earlier. And he didn't even remember, I mean, it wasn't like he got anything from it. He wasn't trying to obfuscate down the road. He just did it unthinkingly as a 23 year old, you know, guy filling out a corporate form and it caught up with him.KK Anderson (16:14)Wow. So speaking of the resume, you know, and sales leaders, you know, lot of, a lot of sales executives are going to lead with the numbers on their resume. So when what firm like yours is starting to dig deeper, like what are you really wanting to understand about those, like how those results were achieved? Right? Like what, what do you want? What do you want? How do you want the sales leaders to show up and talk about those results and those outcomes?Jason Baumgarten (16:37)Yeah, there's a few things. First of all, what was going, what was the context, right? What was going on around that industry? Are you actually showing me the best numbers you have, but they're the worst numbers of any of your competitors? So the more you understand the competitive landscape and your peer group, the better. The second is what was the momentum when you caught it, right? If it was going up 30%, now it's going up 20, you can tell me how amazing you are that you hit 20, but actually you decelerated the rate of growth. So I want to understandwhat happened because that's actually a story of negative, you know, negative impact, even though it's a positive number. The third thing is do you seem to understand what you did to achieve those numbers? Right? And that's a recurring theme that you'll hear from me. But, you know, do you have clarity as to what you did? One of the most common things is people who are in jobs for very short amounts of time, but the numbers were good. They're like, Oh, yeah, I was there 18 months, but wow, we crushed it.crushed it so amazingly, I could go on to the next role. And I'm like, let's unpack how you crushed it in 18 months, because it took you six months to find out what the name of the people what, where the bathroom was, and what the names of everyone on the team was, and what the products were all called, and blah, blah, blah. Any human being, takes months just to normalize. And then it probably took you three to six months to find your next gig. So in that short time, you were actually working enough to speed, what did you do?And if the answer is kind of fuzzy, it's not that I worry that they didn't have a great 18 month tenure, I worry that they're so busy trying to tell me that they did something they didn't, that that demonstrates how they show up as a leader, and how they show how they show up as a as a colleague on a team. And that's way more concerning than that they didn't have an amazing 18. Anyone who's at somewhere 18 months, and probably it wasn't an amazing run. I mean, the odds are good that if you're there less than two years,Something went wrong, whether it was up to you or not. Something probably went a little off. That's fine. Just own it. Just be like, hey, that wasn't so good. Or it was so good that it led to this next thing coming out of the blue. But also have the humility to be like, I inherited a great situation, didn't screw it up, as opposed to saying I did everything and I'm amazing, because things just take time. I mean, in 12 months, you can't turn around that much.Mark Petruzzi (18:41)Jason, and thank goodness that companies are doing this and focusing and figuring out how they can get senior executives that are ethical and honest and trustworthy. Because if not, who knows what our general economy would look like. ⁓ Because it's one thing if you hire a sales rep who maybe is a little unethical, you figure it out, you you...you move on that individual. But if you hire your CEO, CRO, and Chief Operating Officer with those kind of backgrounds, it's going to come out. It's going to show up at some point. so I'm really glad to hear the, I've experienced it myself in the vetting process, but to hear you articulate it takes my understanding to an even greater level.Okay, we just have a couple minutes left. We love doing these rapid fire questions that we do with our guests and I'm really interested in hearing your responses on these. So what was the first product or service you ever sold?Jason Baumgarten (19:43)I sold jewelry. I bought jewelry wholesale and sold it at street fairs.Mark Petruzzi (19:48)I like that.KK Anderson (19:49)That is so cool. How old were you when you did that?Jason Baumgarten (19:49)And you learn a lot selling jewelry.I was like 14.KK Anderson (19:52)Really cool, wow. You knew you would be going to Stanford at that point. The entrepreneur at 14. ⁓Jason Baumgarten (19:57)⁓ I knew I loved business. I knewI loved business.KK Anderson (20:00)Jason, who's your favorite CEO or business leader that you've worked with over your career?Jason Baumgarten (20:05)You know, I have so many, this one's really hard. I actually find that I learned so much from so many of the CEOs I work with and they're all amazing at certain things and they all have ⁓ foibles. I think that rather than share the person, I'll share the story. A CEO that has had an unbelievable career. He always takes the time to learn and get better. AndHe's got coaches, he's got advisors, he's got, but he's just a learner. you know, he's one of these guys, it's a household name, but you reach out to him and he says, I'm busy. sitting down with a 24 year old to learn about how to do better prompting. I'm like, you're retired. What are you doing? He's, I got to get good at this. It's really important. And I just, I think there's a amazing, the CEOs who keep wanting to get better are just really inspiring.Mark Petruzzi (20:51)Yeah. So a resource every aspiring board member should use.Jason Baumgarten (20:55)their network.Mark Petruzzi (20:56)Excellent.KK Anderson (20:57)That's a good one. Okay, my favorite question is not listed here, so I'm gonna go out on the limb and say it anyway. Jason, what advice would you give your 21 year old self?Jason Baumgarten (21:07)Take more risk. I think that's the thing that we underestimate when we're young is that you can recover, can do, you can get a do over. People are very tolerant of youthful, ⁓ you know, behavior. don't mean behaviors in a social sense, but you know, just try to start your own company, try to join a startup that's a high flyer, try to, do something that's risky, because when you get older, it's much harder to take risk for all kinds of reasons.So do it when you're young and within whatever is relevant to you. You might be the most risk-seeking person out there But you know, would say I think most people when they're young They squander good risk They take a lot of risk in their personal lives and not a lot of risk in their professional lives And I'd say take some professional riskMark Petruzzi (21:47)Excellent. Well, Jason, thank you so much for your time, your great analysis and answers. We will add for our audience here, we'll add a bunch of show notes and make sure you get to read some of the good stuff that Jason has put out there and learn some more about him as well. yeah, so thank you, Jason. Thank you to our amazing audience.We so appreciate you and thank you to my co-host, KK, as well.Jason Baumgarten (22:16)You guys were fabulous. Thank you.KK Anderson (22:17)Thanks, team.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.