In this episode of Selling the Cloud, Mark Petruzzi and KK Anderson are joined by Jason Baumgarten, Global Head of the CEO and Board Practice at Spencer Stuart, to unpack what truly separates sales leaders who advance into CEO and board roles from those who remain stuck at the functional level.
Drawing from more than 250 CEO and board transitions, Jason shares a rare behind-the-scenes perspective on how boards evaluate CROs, why ambition alone is not enough, and what sales leaders must change as they move from execution to enterprise leadership. The conversation explores founder-led transitions, boardroom presence, customer lifecycle thinking, and why sales excellence alone does not guarantee executive readiness.
This episode is essential listening for CROs, founders, and revenue leaders who want to move beyond quota and operate at the highest levels of leadership.
What You’ll Learn:
Key Topics:
Guest Spotlight: Jason Baumgarten
Jason Baumgarten is the Global Head of the CEO and Board Practice at Spencer Stuart, where he leads executive search and board advisory engagements for companies ranging from early-stage ventures to multi-billion-dollar enterprises. He has advised on more than 250 CEO and board transitions, with deep expertise in founder-led technology companies, succession planning, and board effectiveness.
Before joining Spencer Stuart, Jason was an Associate Principal at McKinsey and a Program Manager at Microsoft. He holds an MBA from Stanford Graduate School of Business, serves as Chairman of the Board for IslandWood, and is a frequent contributor to Harvard Business Review, including his article How CEOs Build Confidence in Their Leadership.
Resources & Mentions:
• Spencer Stuart
• Harvard Business Review: How CEOs Build Confidence in Their Leadership
• Mark Roberge: The Science of Scaling
🎧 Listen now and follow Selling the Cloud for conversations with leaders shaping the future of go-to-market, executive leadership, and board-level decision making.
Mark Petruzzi (00:37)
Welcome to today's episode of Selling the Cloud Podcast. I'm thrilled to welcome Jason Baumgarten, Global Head of the CEO and Board Practice at Spencer Stewart. Jason leads Executive Search and Board Advisory for one of the world's premier leadership consulting firms. He's completed over 250 CEO and Board Transitions.
across companies ranging from early stage ventures to multi-billion dollar enterprises. His expertise spans CEO succession planning, board effectiveness, and leadership transitions, particularly for founder led technology companies. Before Spencer Stewart, Jason was an associate principal at McKinsey and a program manager at Microsoft.
He holds an MBA from Stanford's Graduate School of Business and serves as chairman of the board for Island Wood. His thought leadership appears regularly in the Harvard Business Review, including a recent article, How CEOs Build Confidence in Their Leadership. What makes Jason's perspective uniquely valuable is his vantage point. He's interviewed thousands of sales leaders and observes what
separates those who successfully transitioned to CEO and board roles from those who just can't get there. Today we'll explore four critical themes. The sales leaders evolution from operator to strategic executive. Founder transitions building a leadership capacity beyond the go-to-market motion. Board governance for sales leaders. Why thinking like an investor makes you better at your job.
and landing your next role, what really matters at the senior executive level. So I guess a couple of things there. You really don't work hard enough or really haven't accomplished most in your life Mano man, Jason, what an amazing career you've had already.
And I'm sure you're not going to be slowing down anytime soon. So thank you. Thank you for joining us and joining us here on Selling the Cloud podcast.
Jason Baumgarten (02:40)
Well, thanks for having me. And I felt a little tired listening to it, but it was all fun in the moment and delighted to try and share some learnings from the many, many, interviews and board discussions and CEO discussions with your listeners.
Mark Petruzzi (02:53)
Yeah, and Jason, we have an audience of mainly CROs, some of the best in the business. And, you know, there's a number of them that I've already prepped to make sure that they've watched this because they're looking at the things that you do. ⁓ And I have many CRO friends who join us as well that have made this transition. So I love the, I love where we're going here and excited.
to dive in. Topic one, the sales leaders evolution. How do you evolve from somebody who's great at sales to configure out management and understand leadership, and then they really have to move to the next level as a strategic executive, often without the background, not to say an MBA or a more prominent type of... ⁓
educational background gives you all the recipe to do it as well, but many of them, you know, just they feel like they don't have that. So in your interviewing of thousands of sales leaders, what fundamentally distinguishes those who you feel can successfully transition to the CEO role or to board roles from those who just you feel maybe we'll struggle with that?
Jason Baumgarten (04:04)
Yeah, it's a great question, Mark. I mean, first of all, it sounds perhaps silly, but I start with do they really want it right? And the reality is not everyone really wants to be a CEO once they learn what that role is all about. ⁓ And so you have to start with not wanting it for ego reasons or control reason, but really do I want to do that job more than the job I'm doing today? So that's sort of step one. It's important. A of people breeze right through it, but I'm like, no, actually, do you really want it? And why do you have
thought out reason why. The second thing is, you know, sales, ultimately, I think have a sales leaders have a couple of critical advantages. One great sales leaders have real industry and customer intimacy, and great organizations are built around solving customer needs. And so if you can really lean into that proximity, that superpower, that's super helpful. The second is most sales leaders are great people leaders.
And so if you're really thoughtful about how do you lead a team? How do you lead people? That's another thing to lean in. What are the areas they tend to be less good at? Well, the first is genuine curiosity, right? One of the challenges with sales is one can become quite transactional. How do I hit my number? How do I move the sale along? How do I move the conversation along? How do I get what I want done, done? And the reality is great leaders are deeply curious. They're deeply
interested in learning about other functions, other aspects of the company. So the first thing I'd say is tap into your innate curiosity to learn about what's going on in finance, what's going on in legal, what's going on in product, what's going on in marketing, what's going on in customer success. So that as you evolve your thinking, you understand more about what's happening in other functions. The third thing is actually rising up.
and doing two things. First, think as a systems thinker about how do all the pieces of the puzzle fit together to make revenue and profit happen and get knowledgeable about that system. And then two, ensure that you are not coming across as somebody who believes sales is the answer or the cause of all problems or solutions. So those are a few of the things that I'd share. We can go into more depth on any of them.
But there's some of the high-level things if I had to add a final one, I'd say humility I always laughed that if I interview all the top sales leaders at a company that revenue will beat will go up at least a thousand percent from the interviews alone when you just add up all the numbers and of it is there's an amazing quality of confidence and You know that a lot of sales leaders have but recognize that when you're interviewing for a CEO role or for something else you've you've got to temper that a little bit with
Mark Petruzzi (06:24)
Yeah.
Jason Baumgarten (06:40)
that empathy, that curiosity, that humility.
Mark Petruzzi (06:42)
KK, I think you're on mute.
KK Anderson (06:43)
Well, that's a first for a podcast to land. Jason, really interesting what you're saying. And you've said that board members can sometimes be like Christmas lights. Like, you know, they turn on once a year, right? And so for a CRO walking into, you know, a board meeting, like, and thinking about how, how...
Mark Petruzzi (06:46)
Yeah.
Jason Baumgarten (06:46)
Yeah.
KK Anderson (07:05)
What advice do you give? Maybe they're not aiming to be CEO, but what advice do you give them around not just being seen as a salesperson? Talk to me about that. Talk to me about a CRO walking into
Jason Baumgarten (07:15)
Sure. You
know, first and foremost, it's think about your stakeholders and most salespeople do this really well. So think about who's around the board and what matters to them. What are they thinking about? What's their what did they show up worried about or excited about in that board meeting? And I don't mean conceptually and for all time Memorial, but like in that meeting, what's on their mind? What's going on in their companies? What's going on in their investment groups? If it's a public company, what's going on in their day jobs or their other boards?
What is the context? know, are you, are they walking into a new product launch being announced at your company? Are they walking into a bad quarter? So the more you start with who am I presenting to, who are these people on the other side, not just in the singular dimension of them as your board member or investor, but also the rest of their lives. So that's sort of step one. Step two is to your question of how do you appear as more, you know, how do you present a more holistic perspective? You know, I think
It really comes from that ability to connect the dots between what's going on with your customers and the market, you know, competitive point of view, you know, customers need shifting product evolution, technology evolution. So that's one. And then the other is being able to connect the dots inside the company. You know, we did this thing on, ⁓ our customer support initiative. It had this impact on renewals. This then led us to be able to change the way we're going after new logo.
The more you can stitch together narratives that are multidisciplinary, the more they start to see you as not a one-trick ⁓ answer. And the other thing I'd say is know when the answer is not sales. One of the most powerful things any functional leader can do is to say, that's a great question. I actually think the answer is in marketing or is in HR or is in finance or is in customer support.
You could give us more resources and sales, but that would be the worst place to put the capital to solve that problem. Because showing that shows that you are stepping out of your functional role to really think about what's best for the company and how you as a systems thinker would apply that capital or that resource.
Mark Petruzzi (09:15)
Jason, so in general, when should a CRO start thinking about building the capabilities beyond the pure sales, execution, sales leadership side? What's the signal?
Jason Baumgarten (09:27)
So I think there's two things that are working in tandem. One is their ambition, right? Do they have ambition to do more bigger, more complex, even sales roles or CRO roles that are broader than sales? And then have they mastered where they are? So at a very simplistic level, do they feel like they've kind of got the, you know, the training wheels off in their current role? You know, do they have sales ops team leadership, you know, forecasting
KK Anderson (09:37)
it in that
Jason Baumgarten (09:49)
all those key skills down, if they do, it's a perfect time to now start to think about how do I broaden? If you haven't got those mastered, you know, probably need to spend time there. But if you feel like you've got your quote unquote day job in good order, it's only going to make you better in your day job. And that's I think one of the things people often forget is they think, I'm doing this to become a CEO or to become a board member, or to take on more, it will actually make you much better in your day job.
because you'll start to think about ⁓ other levers you can pull with your colleagues to help move revenue beyond what's in your control. And that influence in your leadership team, you will be more effective because you won't be seen as somebody lobbying for your team's resources, but for solving, know, every function wants more revenue, more profit. So when you start solving for that, you become an enlightened sales leader who,
everybody wants to pull into their opportunities, their, you know, their initiatives, et cetera.
KK Anderson (10:46)
Isn't that the truth? Yeah. Jason, let's move on to the second topic and talk a little bit about founder transitions and building, as you've been discussing, that leadership capacity beyond just the go-to-market motion. And you have worked with many famous founders, ⁓ and you've had the ability to see a lot of these founder-led companies up close. And so I would love to hear
you know, maybe a story or two about some of your, your favorite famous founders that you've led. and then specifically like when, when they stopped becoming the primary salesperson, right. And the company starts to scale. I'm curious, like what usually breaks first, right. And just talk, talk us a little bit about some of your, favorite famous founders.
Jason Baumgarten (11:30)
So I think I've worked with almost all of them in some form or fashion. ⁓ You know, I would say that what tends to break is sleep. If I'm realistic, it's, it's the thing is you just only, no matter how amazing somebody is, they only have so many hours in the day. And so that's one. I think the other thing is that, you know, and you know, this as well as everybody ⁓ who really is an expert in sales, the one-on-one connection of an individual can only scale to so many people.
KK Anderson (11:36)
Okay, there we go.
Jason Baumgarten (11:54)
And so I think what starts to happen is that while they typically are doing more of a business development motion, more than a real scaled sales motion, they start to realize, I need some channel sales. need some indirect sales. need some marketing driven conversion. I need more tools in the basket. And then they start to build a sales team beyond them. Now, I think the early sales leaders of many companies
are individual contributors themselves. And so there's almost two evolutions. There is the first, you know, it's the founder being the salesperson, and then there's the first salesperson being the only salesperson. And then it's you as a sales leader kind of going to the next level as a ⁓ building a team, building a, you know, a model of sales. So I think that's often the trajectory these companies go through. I would say the other watch out is
Mark Petruzzi (12:28)
Thank
Jason Baumgarten (12:42)
founders who have a couple of really good early deals and think, boy, this sales thing is easy. And then they start to scale it. And they realize that that was just friends and family. And people thought it was great. Or they got some early pilots and it's not easily replicable. And so I think when you really ⁓ move from founder stage to a growth stage is when you can replicate that journey, when you know that you can hand this to someone else and Mark can go sell.
just as well as I can. Founders are always going to have a special edge, right? The reality is if a founder calls a company, they're always going to have a little extra time. It's a little easier to get through to an executive, but until you can replicate it, you really don't have a repeatable sales process. ⁓ You know, I would also say that what we're seeing now is a real evolution in how people are thinking about it, because you are also seeing ⁓ much more complex sales motions.
And in some cases that's complex because we're seeing them look more like consumer sales motions. And in some cases, much more like consulting or professional services. So we're seeing more bifurcation than for a while we were into the fairly low complexity SaaS sale, you know, and that is on the edges starting to fray a little bit in terms of just the complexity of, the heterogeneity of all the different types of products and services we're seeing in technology.
So maybe avoiding a particular person, but, you know, I think everybody goes through that wave and, you know, I worked with one leader who his startup was in the sales technology space. And that was perhaps the most incredible cause he was one of the best salespeople period. And he was one of the best salespeople for that company, even when they were at, you know, several hundred million dollars in revenue. But he realized he had other things he had to do. And if he spent all his time selling,
So what he started doing was spending more time teaching and making sure the right process was in place to scale as opposed to saying, I could do that better. Because of course, but he also couldn't do everything. had to, he had to pick what he was spending his time on.
KK Anderson (14:38)
Especially if he wanted to sleep, right?
Mark Petruzzi (14:40)
Now that Jason, that is spot on. So in some of your publications, articles that I've read, you mentioned two critical dimensions. Building the right go-to-market engine as one aspect of it. And then at the same time, readying the organization for when it's not founder led sales anymore. And they're not spending 50, 70 % of their time on sales.
How should boards in particular approach these transitions? What responsibilities do they have in all of this?
Jason Baumgarten (15:13)
Yeah, it's a great question. It does depend on this on the type of board and this, even for startups, what's the type of startup and the ambition of the startup? You know, I think the thing that boards should spend the most time on is what is the theory of the sale? Like what is the theory of the sales system that the company is starting to move towards when it goes from an individual to a system? Second, based on the data, you know, the early returns early data,
is that hypothesis or theory holding true, right? So for example, if we say, we're going to sell into this ⁓ type of executive, we believe it's get a demo, show the demo, do a pilot, you know, whatever the the march you're taking people through, is that actually proving out in the early data? And then the third thing is, is the company continuing to appropriately experiment and test whether they have the right model? Because I think it's probably the most
dangerous thing is to very early and we see this when an executive comes in and says well I've heard it I know the way to sell is XYZ and I'm gonna bring that into this startup and it isn't the right model right something is off either the ideal customer profile is off or the literal ⁓ you know Approach is off or the pricing is a little bit off Something in there is a little off and instead of catching it early. They catch it really late That's really bad for that sales leader, but it's also really bad for this
for the company. so board members can really try to make sure there's a crisp hypothesis as to here is how we're going to sell. Here is the data that's going to show us that we've got the right model. And then three, are we seeing reinforcement that we picked well, or lessons learned that maybe we've got something off and what are we doing to adjust. ⁓ And then you can start to diagnose what's going on if you're not hitting or beating your expectations, you can say, we had something wrong. And that's okay. I think
The worst thing is to double down and say, we just aren't trying hard enough. It usually is a strategy or a process problem, ⁓ not a try harder problem. You know, unless people are just flat out lying about what they're doing, but I don't find in, especially in startups, people are usually pretty excited to grow the company. And so they're showing up, you know, trying to kill it. The other thing is not recognizing that whatever works early is probably not the forever model. And
For example, there was years ago, an enormous number of SAS companies that had very low cost direct models. And they realized that that wasn't going to scale that they needed to get a more enterprise motion. And yet they built teams that were so well oiled for a particular model that when the when the growth rates started to slow down, they didn't they weren't as quick to transition or try new things. And that's a failure. The know, it's a failure of the leadership team. But
even a failure of the board because the board should have been asking those questions earlier than the executive team because the board's role is to try and look ahead of where the executive team is is reacting to right now because the executive team might be You know 70 % reactive 30 % planning the board should be the other way around and should be able to say hey I think this is going to come and hit you in a year or two years. How are you prepping for it? Now? What are you doing now? How are you learning now? So that's how I think about that board interaction early on
KK Anderson (18:14)
You know, we were just interviewing Mark Roberge this morning on the release of his upcoming book, The Science of Scaling. And he was talking a lot about, you know, an early, you know, indicator of retention around, you know, customer success. And so for a sales leader, you know, they are a CEO might be thinking like, hey, just get us more leads, you know.
get it, we just need more pipeline. Pipeline will fix everything, especially in these early stage companies. And Mark's argument was actually, what you really should be focusing on is your retention. Like, are you hitting those benchmarks that show that people, your customers are staying and you have, you know, product market fit, you have go-to-market fit, your customers are there and they're coming back and they're renewing. So, you know, talk to me a little bit about kind of your perspective on
on that idea and what are some, like when you see founders, you know, start to show maybe a lack of leadership or like you're like, I want to coach them to increase their acumen as their companies grow and scale. And you need to take into consideration things like, you know, the retention metrics, you know, more so than the sales metrics. And you said earlier, recognizing that sales isn't always the problem.
Like what does all of that make you think of? what's your perspective there?
Jason Baumgarten (19:24)
Yeah.
I mean, first of all, I think he's spot on and I'd go so far say, you know, you want your metrics across the whole consumer lifecycle, you know, the whole client customer lifecycle, because it may be showing up in retention, it may be showing up in a lack of cross sell, it may be showing up in different areas. And the point is not to say we did a good or bad job, let's understand what's going on. It may be that you're got great conversion, but with all the wrong clients. And the real issue is you're going after the wrong clients, the wrong customers.
not ⁓ that you are incapable of turning those leads into opportunities. So I think the first thing is I'm a big believer in capture the data across the whole life cycle so that you can understand what's going on with the sales approach, you know, depending on the type of product we're talking about, the, you know, the onboarding, the services side, the customer support side, et cetera. So I think that whole life cycle is critical. I think that when, ⁓
You know, when founders are finding themselves stuck, usually the answer is go talk to people who have done who are a little further along in the journey than you are and ask them for advice and counsel about what worked for them. And don't take one person's advice. Don't say, well, you know, one investor told me the answer is this metric. So I'm going to go chase that metric, triangulate different people, get a good kitchen cabinet together.
and ask different people and don't just ask peers, don't ask other founders alone, don't ask other CEOs, ask people who are in CRO roles, ask people who are individual salespeople, ask people who are in other parts of the ecosystem so that you're hearing perspectives from, you know, the person who might be junior entitled to you, but much higher than you in scale. You know, I always laugh, you can be CEO of your own business, just pop a magnetic sign on your truck and drive around and Mark's got Mark and Co.
He's a CEO done. You don't, you don't need to actually have a company to be CEO. Same thing with the sales person, right? If you're selling lemonade, you're a sales person. But if you're, you know, you could be a very junior person selling millions of dollars in a very complex way for an enterprise SaaS company, or you could be a founder who's got a big title and a lot of sense of importance, but you're selling half a million dollars. And that doesn't make you more sophisticated as a sales strategist and the person who's a
Mark Petruzzi (21:09)
Mm-hmm.
Jason Baumgarten (21:36)
senior manager at a big SaaS company. So don't just think about your peers. Think about, you talking to people in different roles and different scope and scale? And to me, that helps you understand what's going on. It also gives you empathy because when you start thinking about things like incentive plans or how to inspire the team, you also are thinking about, wow, how does that work when you've got 40,000 people?
I've got five, how does it work at 40,000? So I think the more they can get out of their own atmosphere, it helps a lot.
Mark Petruzzi (22:08)
So Jason, I'd like to take you back to the board perspective for one more question here. So what mistakes do boards typically make in the timing and structure of hiring professional sales leadership as they move from a founder led selling motion?
Jason Baumgarten (22:26)
Well, I think that I think the two biggest mistakes I've seen is they don't do it early enough. Right. There's a sweet spot. If you do it too early, you don't, you don't have product market fit. There's no point in bring on your professional sales leader. If you wait too long, things get pretty calcified before somebody has a chance to think about your incentive design, your partner design, your channel design, all those things. I would say the other piece of the puzzle is hiring somebody who is going to bring the
And if you don't, you know, you can either start with a very open mind, you know, classic beginner's mind and say, I don't know what model, but I'm going to use this recruitment to help figure that out. Or you can do the work to say, we've actually figured it out. I figured it out or your team has figured out. And we now know what kind of sales leader you need, because if you believe your PLG and you're really not, you can hire the absolute wrong person. And that's not good for anybody. And I'm a big believer that there's, there's
there's not good and bad sales leaders. There's not good and bad leaders is actually people who are the right fit for the right time. And so you need to make sure that the fit of that sales leader is what you need. ⁓ The third thing I'd say is sometimes they just over, ⁓ you know, there's a desire to sometimes signal a Rolodex and get somebody who's got a big Rolodex. And maybe because I'm in the Rolodex business, I always laugh. like, listen, if you've got a product that's solving real problems,
getting access and the Rolodex will be the least complicated thing. And people want problems solved. And so if you really have a good solution, you will find a way to those people. That is probably the least value in most industries. That's probably the thing I would not get hung up on early. And yet I think a lot of founders think that's the magic unlock. The reality is most human beings at best,
best have 100 to 150 relationships. And that's actually overstating the real quality of most of those relationships are ⁓ not preferential. Meaning if you and I have the same product and we both go, I'm not going to win it just because I have that relationship. It's really going to come down to who is the better product. And so I would say don't over bias to that concept of access.