How Private Equity Evaluates CROs with JD Miller

Hi, I'm Warren Zenna, founder and CEO of the CRO Collective, and welcome to the CRO Spotlight Podcast. This show is focused exclusively on the success of chief revenue officers. Each week we have an open, frank, and free-form conversation with top experts in the revenue space about the CRO role and its critical impact on B2B businesses. This podcast is the place to be for CROs, sales and marketing leaders who aspire to become CROs, and founders who are looking to appoint a CRO or want to support their CRO to succeed. Thanks for listening. Now let's go mix it up. So if you don't mind, I mean, great, because you're really quite, quite accomplished. You know, there's like a lot of great stuff that you've written and you're a voice in the CRO space. And as you know, I mean, this is my domain for my life as it is yours. So it's really good to have this conversation with you. And if you don't mind, just like as you can, it's a lot, but if you can give like an overview of your career and who you are and how you got here and some of the stuff you've done and maybe even if you don't mind, maybe as succinctly like what your general sort of philosophy is, like what would you say is the kind of specific thing that you're saying in the marketplace today? What's the theme from you?

Sure. So career progression, I'll start there. I did not intend to be in sales. I began college thinking I was going to be a lawyer and I went to school with a very traditional pre-law curriculum of communication, philosophy, and comparative literature. So thinking, writing, and speaking. I had an internship in the Clinton White House that changed my mind about being a lawyer. And I looked back at my undergrad degrees and I said, well, I'm not going to be a professional philosopher and I'm not going to be a professional comparative literature. So what can I do with this communication degree? And it was the '90s and the internet was just happening. And the communication school said, why don't you stay and work on a master's in group communication and really How is communication being influenced by this new thing called the internet? And, you know, that led to ultimately a PhD in social networks and how social networks form online, which also opened doors to Verismall.com. So my career then was a series of sales roles. I began as a sales engineer, grew up through the management ranks in B2B tech. I've been CRO multiple times. And then 5 times those companies were owned by private equity firms. And so my real specialization has been how do you lead sales in a private equity context? And today I work for a private equity firm itself, as they call me CRO in residence. I'm the coach to other CROs. If you're owned by our firm, I'm gonna be your best friend and guide for the time that we work together.

I love it. That's awesome. So I just wanted to just touch on something. It's fascinating. So what was it about your stint at the Clinton administration that had you think you don't want to be a lawyer?

Well, I don't know. Your listeners are probably younger than me, but if you remember the summer of '96—

No, I'm the same age as you, by the way. You and I are the same age probably. So I might even be older than you. So my listeners are actually probably old, as old as us, I think.

Sure. So if you remember the news headlines of '96, the Clinton White House interns were in the news a lot. I was not necessarily making the headlines, but I definitely got to see, you know, the behind the scenes kind of drudgery of, you know, how people needed to deal with all of that. And I thought a lot about the traditional kind of lawyer's job. It's really long hours. You're really not in control of when you're going to be needed. And I just, I could tell that that was not the career that I wanted. Sales worked out to be great. It is long hours. You know, customers, you still don't always get to control exactly when you're needed, but it's been a lot better control of my life being able to, you know, use my communication skills and meet people and learn about interesting businesses, but also not be billing by the hour every minute of every day.

Okay. Again, it makes sense. I mean, the good news, I guess, you didn't have to become a lawyer to figure out you didn't want to be one. You just kind of watched it and you were like, okay, good. I don't want to do this. I get it. That's, that's a nice avoid there. So, you know, most people—

I love school tuition too.

Yeah, exactly. No, it's nice. It's good to be able to like, you know, watch someone cook in the kitchen. It's like, I don't wanna do that. So I would say from what I'm hearing, you know, most people think of you as sort of like the CRO of the year, you know, a PE scaling guy. But I keep coming back to something else, which is, you know, you're a licensed food sanitation manager. I mean, you ran kitchen operations, right? For homeless people. Yeah, the company called like Care for Friends, right? So what did that teach you about leadership that the boardroom didn't? Yeah, I'm just curious to know, like, you know, that's a very interesting— like, you have this very humanitarian side to you and you also run PE. I'm just curious how you sort of manage those two kind of paradigms.

Well, you've done your research. So, um, so there actually is a little bit of a PE background. Um, I was living in Lincoln Park, which is A nice neighborhood. Yeah. Chicago. And there was a church down the street, street that I was volunteering in their homeless organization. And probably about 15 years ago, the pastor at that church or priest said, hey, you're some kind of finance and private equity guy, right? And I was like, yeah, you're some kind of a religious guy, right? You know, where does this go? And he said, well, you know, my CFO, you know, gives me these spreadsheets every day. We're trying to build a new building. I'm not sure I understand how to read all of this. Would you work with me to help me understand the finances of that business? And so we looked at it and they were facing down a $10 million capital campaign and they did not have enough families that were going to support that. And so we talked about kind of a, kind of a private equity type move. What would it be like to take all the homeless services and spin it off from the church? Because it wasn't religious based. And if you do that, you open up your doors to a bunch of different donors and, you know, government sponsors and so on. So I, first of all, became the first president of the board of Care for Friends when we incorporated as a nonprofit. And then because we serve, you know, hot meals to 150 people every day, it is like running a restaurant. So someone has to have a food license. And I became that guy at the beginning of the year. And so it's, it's actually a totally different part of my brain. I got to take— every 4 years you have to go through a certification process, and I do my continuing education with a woman who's a pastry chef at the Four Seasons. So she teaches me all kinds of things about chocolate and sugar sculptures and things that we're not serving in the homeless shelter at all. But, you know, I get certified in sushi and safe fish handling and all the rest of it, which is really just an interesting side of things I can do at home when I'm not reading spreadsheets.

That's awesome. I love it. So, you know, now you taught me, you're like, you're a PhD and then you go work for the Clinton White House and then you went to sales. Like, I'd like to hear more about that leap. Like, how did that specifically happen and what were you looking for in that move? Like, why that? There's a lot of things you could have done and not done. What, why, why selling?

You know, I'd like to say it was intentional, but some of it was just being lucky and being in the right place at the right time. So at the time I had done this research in group communication and how that happens online and a recruiter called and said, I'm looking for a, it was actually a sales engineering role at a very small dot com, 26 employees. And they found me because they didn't know someone could have an advanced degree in online social networking in '96 or '97. And initially I heard that word sales and I thought, I want nothing to do with that. Those are the people who, you know, call you on the phone in the middle of dinner and, you know, try and sell you a credit card you didn't need. But the recruiter explained that, you know, for salespeople in general, and especially for sales engineers, you're really solving people's problems. You're, you're using your teaching skills. You're explaining how technology is going to help advance a business goal. And so I took the leap and joined. I didn't realize what a very small company it was. But 6 years later, it had become the world's largest tech company to go public with a $9 billion valuation. Google eventually took that title from us. And I was hooked on, you know, the job, the meeting the folks, and, you know, commissions were great too. And so eventually I shifted over and instead of being the demo guy, I, you know, picked up a bag and carried a quota and became a a sales executive and then ultimately managing teams and CRO and, and all the rest of it.

That's interesting. So then you went from sales, did you jump into a sales leadership role, like managing sales teams and building sales organizations, or did you stay as an individual contributor? Like, how did that progression happen before you became more, let's call it like more like an operator as opposed to an independent contributor?

Yeah, I was an individual contributor twice, uh, for two different companies. And they were both tech companies. And then there was a consulting firm in Chicago that had been implementing a lot of my software and they were looking for a chief marketing officer. And I don't know what they were thinking, but they knew that I had sold a lot of software that they had implemented. And so their managing director called me one day and recruited me to be the, you know, marketing director is the role they called it there. And so that was my first jump into leadership was a totally new company. I never had direct reports until I was sort of installed at the head of marketing. It was a really interesting experience for 2 years. I learned a lot of leadership lessons. I also realized how much I didn't know about marketing, how much I didn't know about people leadership. But it was enough of a taste that said, you know, this is the career that I want. I want to get smarter at this. Maybe I should go back and manage salespeople because that's really, you know, what I really know how to do. And then that sort of began the next job search as VP of sales and then, you know, kind of progressing all the way through, you know, country president. I did a lot of international companies and then ultimately CRO and now board member.

Got it. So when you were running that marketing organization, this is interesting. How did you navigate being someone that ran marketing and not having done any before? Like, what was your way to survive through that 2 years? Did you have to, employ people that did know and learn from them, or did you just read a lot of books, or what? I'm just curious how you kind of pulled out that one, having not knowing how to do that before.

Yeah, I mean, I was fortunate that I inherited a marketing team who really did know what they were doing. Um, so there was a, you know, creative designer and, you know, all of those kind of folks who, who had sort of the tactics. And then honestly, it was people like you. Um, you know, podcasts, user groups, internet discussion groups. This is, you know, the kind of early 2000s where, you know, I still remember a podcast that was just about leadership and all of the basic structures of, you know, how are you running one-on-ones and what are you looking for when you're doing recruiting? And it really became sort of a management training program that, you know, whether you apply it to a marketing team or sales team or, you know, much bigger organizations, a lot of those basics of leadership tend to be the same.

That's interesting. It's almost like you were— found yourself in a situation where the competencies were there, they just needed leadership, and you sort of filled that void. And you obviously had an ability for it or a propensity for it already, or else you wouldn't have been able to do it. I don't think you can just become a leader if you don't know how to have, like, an innate ability for it. That's fascinating because I've just seen so many people get thrown into a situation like that where they sort of have to do everything and they just can't make it through. So it seems like you have a, maybe similar to me in a lot of ways, kind of a good knack for finding yourself in really great situations where things present themselves that you can kind of rise to the occasion. So I'd be curious—

Definitely always said yes. Yeah. To new opportunities.

Exactly. You're right. You say yes to things and you sort of figure it out, but sometimes you don't. I mean, I've said yes to things I didn't figure it out, but that's okay. I learned more from my mistakes than my successes. That's for damn sure. But curious about like, so you mentioned CRO, sales to CRO. So I want to make sure that, and I suspect we probably agree on this, but I'd be interested in exploring this a bit. Right now, you know, you're talking to PE firms. What's your standard sort of rote definition of what a CRO does?

They are the person who ultimately owns every dollar that comes into the business. And so sometimes people think that just means running sales. And of course, your sales team is a big part of that, but it's also the channel, it's resellers. I've done a lot of B2B financial products. And so it's been, you know, managing the revenue streams that way. Sometimes marketing is reporting into the CRO. They're always at least a really good collaborator because what marketing does, you know, is really directly intertwined with how we generate revenue at the end of the day.

Yeah. Okay. Well, good. We're on the same page there. So yeah, I'm a bit more doctrinaire in the respect that I think that marketing always should report into the CRO. It's a different thing, but I think there's a reason we maybe get into that. We kind of have an interesting conversation. I know that it always doesn't, and I understand why. I've seen a lot of reasons why it doesn't, and I understand those things. But I think that I've seen in most instances my work I do with the CROs is when they run and they have, let's say, ownership, not executional, but ownership of all those different parts of the, let's call it the incoming dollar, which I think marketing is a key part of. It tends to be more flat and easier to manage, particularly from a translation perspective from customer to the board, which it's just less people involved, less signal interruption, right? But we can discuss that. It'd be an interesting conversation. But so now you, like, were like a scaler, right? I mean, you come into companies that are already sort of maybe have some product market fit and you come in and you scale them. Would you, would you just say that that's probably true? I mean, would you describe yourself as a scaler?

Yeah, I would say my career has always been companies going from about $50 million in annual revenue to maybe $300 million. And in the context of PE, that's usually in a, you know, 3 to 5 year horizon. And so I think, you know, there are a lot of things that people do that I don't have a clue how to do, but I've definitely developed this playbook of time after time after time how to run someone through that journey of, of that particular stage of growth.

Thank you so much again for listening to the CRO Spotlight podcast. This podcast is an important plank in the CRO Collective communication strategy and We're really thrilled to have such great guests on here. So, um, listening and sharing the podcast with other people is really vital because we want to get as many people listening to this great stuff as possible. A couple of things to note, uh, if you're an aspiring CRO or a recently hired CRO or even an old salty CRO and you're looking to either become a chief revenue officer or improve your chops and gain some more insights and improve your competencies as a chief revenue officer. We offer the CRO Accelerator course. It's 5 years now. It's the first CRO-focused course that was out there. It's a 15-week course that is populated by aspiring chief revenue officers and CROs. We're pretty selective in terms of who can be a member of the CRO Accelerator course. It's people who are probably like more like ready to be a CRO right now. They have a number of years under their belt as a revenue leader, whether it be a sales leader or a marketing leader or even RevOps leader. and they either want to move into the C-suite or they're CROs that want to just make sure that they win in the role. So if you are interested in being a member of the next cohort, please just write me a note on LinkedIn, just DM me, CRO Accelerator, and we'll set up a time to talk. And then I can send you more information to give you a brochure of the course. So again, CRO Accelerator course, 15-week program for aspiring and new newly hired CROs. Take advantage of it. It's been great. And, um, you'll see some more information about it on the website. Thanks. Yeah, it's like usually the place where in our world, typically it's the place where like a true CRO gets their first cut at the job, right? I mean, I've seen, you probably know this, companies who hire a CRO and they're at like $5 million or something like that, and it's really just a title for someone that's actually running a sales organization. I think that's part of, frankly, what's created a lot of the confusion about the definition of the role, but You know, a person that comes in when they're already product-market fit, probably post $30 million, that's someone who has to really understand how to take an existing system and work with it. So I wanna talk about that a bit because one of the main theses for the work we do is that the CRO's biggest problem is that they are an inheritor of a system. They come into a system that exists, now it becomes their system. They have to operate it. And if the system is broken, they're at the mercy of the system that they've inherited and they don't have the authority to be able to do anything about that system. They're sort of stuck with something that is unfixable and they don't have the ability to do something about it. So I'm just curious if you talk a bit about what your thoughts are on that, and kind of your thoughts on how CROs work through that issue or that problem.

Yeah, I love that you talk about that as a challenge. In the private equity context, we are always really trying to grow businesses. And so I talk about it as sort of like flipping a house. You're going to buy a house that maybe has leaky faucets in the kitchen. And you're going to have to replace the plumbing in order to get to the end. And I think that that happens a lot with, you know, companies that maybe are stagnating at a certain size and looking for growth. It doesn't necessarily mean the system is wrong for where they've been, but it may not be the right system for where they're going next. And so I think constantly, and, you know, certainly if you're the size of a company that's hiring your first CRO, you should expect you're probably also at one of those transition points that What you did to get to this point is not what you're gonna do to, to move to the next level. And I think that's a really hard transition for founders to make.

But, you know, I agree. I mean, we're on the same page here, but I think, as you probably can appreciate, I think there's some weird stuff that happens, right? So my clients, they get these jobs, they're hired at the right time, the complexity is there, a CRO is definitely needed at the stage they're at to get where they want to go. But there's a mismatch in a couple of respects. One is the company doesn't really know what a CRO does. They kind of think of one as a sales leader. They plug the person into a functional role and they don't see the results, and then the person gets fired after like 17 months. The other one is that it's a mismatch in that they hire a property builder because they need a property builder, but they actually ended up hiring a house flipper. Who doesn't know how to build a property and they didn't realize that because they didn't evaluate the person. Or what they did was they thought, this person's an amazing house flipper, we can use that person in here. And they come in and they really don't need a house flipper, they actually need a property builder. And so the competency was off and it was likely the mutual fault, but the person just took the job. So I see like there's sort of a combination of things. The onus many times is on the system. And I would say, and I'd be really interested in your perspective on this, PE firms are essentially like system builders. They build a factory across all these different portfolio companies. They sort of try and run a similar playbook 'cause that's how they manage all of them. And they're not always a direct fit for every single company in their portfolio, but in order to manage it effectively, they sort of have to keep things certainly standard so they can just do a better job of managing. And where there's a mismatch, what's the way in which PE firms manage the chief revenue officer in a situation where the company's nuances are a bit different than the way that they want to model out the way they manage organizations, that it makes the CRO succeed. Is this something that you find PE firms are thinking about? I'm curious to know if there's like a consciousness around this definition and placement kind of aspect I'm talking about.

Yeah, so I'll start. The social scientist in me says the solution to all of this is really good communication and really getting very good communication between the PE firm and the holding company or the CEO and the CRO, or, you know, whoever the players are about really what the expectations are. I'd like to believe that at least the PE firm I work for has a unique thesis with every company that, that we're working with. And we should be able to articulate company by company, here's the part of your kitchen that needs renovation. You know, here's how we're going to do it. And here's what we're expecting out of you. It's really important that we all can articulate that and all agree that that's the same thing. Because I think we get into trouble, as you say, like when, uh, our thesis might be about working on profit, uh, but we've got a CRO who thinks it's all about growth, or our thesis might be it's all about growth and we've got a CRO who doesn't know how to think in those ways. And so I think it begins with sort of communication and expectation setting. I also think—

I agree. Go ahead, please continue. Yep.

You know, because you talk about the same thing I do. Average CRO tenure is about 17 months.

Yep, correct.

I think that's often because they haven't had this clear conversation. And so, especially for a first-time CRO, they come in, they do whatever they did to get promoted there, which is probably individual contributor behaviors. You know, they're trying to like be the super seller.

Close the deal.

Every deal.

They want to close the deal.

No question about it. Exactly. Exactly. And the board doesn't want to hear about how you saved the day. You know, the board wants to hear about you've got a team of 20 or 40 or 200 people and how are you strategically deploying all of that. And so if you can get those conversations about expectation really clear, I actually think it doesn't matter what the performance is sometimes. Like you can miss your number, but if we communicated clearly about it and why, what are we going to do about that? You're gonna well outlive that 17-month, you know, time horizon. I think the flip side is true too, that you might be a CRO who's hitting your number every single quarter, but if you can't come to your board and explain why and what you're doing and how that's gonna move forward, they're still gonna look to replace you because, you know, we don't wanna ride that roller coaster.

Yeah, that's great. We're in alignment here. In fact, the whole thesis of the whole way that we go to market with our clients is exactly what you said, which is that the buyer, which is the CRO, right? Or either one is, let's call it the seller in this case because it is usually a salesperson, is going to get a job and they're selling themselves to get the CRO role. And there's two things going on in many cases is they, first of all, they become very emotionally related to this opportunity, almost too emotionally related to it. They see themselves in the role, they see themselves in the seat, they see themselves making all this money, they see themselves with this title and all this stuff that comes with it. It's very superficial from a viewpoint they have. And I'm not saying that they're weak or anything. I'm just saying it's natural. It's a human thing to think this way. And like you said, most of them come out of sales. They have this sort of very persuasive personality that's been rewarded for many, many, many years. And that's just what they bring to the table all the time. It's a winning formula for them. And they do a good job of creating that story. And the other side, though, to make responsible on the other side, is you do have organizations whom, like you said, equally don't have the ability to communicate what they clearly want. They don't always really know. I mean, we see this a lot. You know, they kind of want two things, right? They want the company to grow and increase sales by this number over this period of time. And they also want the company to kind of look better when they do it, you know, and they don't really have a real good program in terms of how to manage those two things, which many times are counterproductively working together, but they have to happen at the same time. So I'd be curious to know, like, what your thought is on what a CRO needs to do, not only at the beginning, which we have a pretty good understanding of that, which is just like you said, like, understand the role and whatnot and the communication. I agree, is more what's the way you would guide a CRO in managing both the short-term and long-term expectations of the role when they don't necessarily coincide in terms of my focus? It's not an easy thing to navigate, and the short-term tends to win because that's more immediate. There's a lot more of a fire drill around short-term goals.

Yeah. So early on, I picked up this sort of annual planning process that really is trying to boil down onto a single spreadsheet. What are each of the assumptions that you have about how you're going to make your number this year? What's going to be new logo? What's going to be price increases? What's going to be, you know, negative, negative revenue because of customer churn? How many more salespeople do you need to hire and how much are you expecting them to grow? And really trying to get that circulated Ideally before the year starts, you're stepping into a role where no one's done that before, you know, as soon as you can get that on a single page and start having every executive aligned on it, every board member aligned on it, having them see that over and over and over again. I think then we've set a score sheet that we can be looking at on the weekly short-term basis. So, you know, every week then I try to send an update that says, You know, here were the 5 big bets we made. We thought we were going to only churn 2% of our customers. Customer sentiment is not doing really well. We churned 7. You know, we thought we were going to hire 3 people. You know, our recruiting pipeline is slow and we've only gotten 1 and we're not going to have anyone else. And so here's what those implications look like in the long term. And then we can have a big discussion about, so what do you want to do now? You know, is there a fire you want me to address today? If so, is that going to distract resources from where we're trying to go farther down the line? What's the downstream implication of that? And kind of keep updating that. I call it the one-page plan. I'm sure you've seen in my book and you hear me talk about it all the time, but that's always been my key to success.

It's great. I mean, I think that there's a— it needs to be a process for this because this is probably the conundrum I see most of my clients get caught up in is they don't know how to navigate those two things. Well, I'm sorry, go ahead.

No. And I mean, that's what happened to me in my first job of becoming the CMO of this consulting company. They didn't really know what they wanted. I think, I think they would have articulated, we want to see revenue grow. And they hired me because I was someone who generated revenue. We never got to the details of, but I don't know anything about SEO and I don't know anything about, you know, brand identity and all the rest of that. And so it was really difficult and I've never managed people or learned how to inspire people either. So, you know, it's hard. And I wasn't smart enough back then to, you know, begin day one, like pulling together the plan and articulating it all. I think I would've had an easier journey for those couple of years if I would've been able to have those conversations earlier and faster.

Yeah, for sure. So, you know, you wrote the book literally, The Zero's Guide to Winning in Private Equity. You know, it's a confident book. There's actually, in fact, if I recall, there's like no chapters on losing. Like there's no case studies on failure. Was that deliberate or is that a blind spot for you? Like, what do you think about like, just, you screwed up big time? Do you know any, like, I mean, failure is a really good teacher. I'm just curious if now that's a part of like the lexicon that you use.

Yeah. I mean, we, of course we lose all the time. I do say in the book, world-class SaaS sales teams really only have a 35% win rate. So we know that most of the opportunities we're in are ones that we're going to lose. What's important to me is that we're assessing the why. And so, you know, certainly as we're going through processes, we're having deal clinics and we're doing all of that. I've really got to remember that in every one of my companies that I've led, we have a pretty sophisticated, you know, loss reporting. We often contract it out to an independent third party to do interviews with our, with our loss prospects to really ask, What went wrong? And I think when you bring that independent third party in, you get really clear actionable things because what does the salesperson say? Oh, we lost because the product was terrible or the price was too high. What does a salesperson say? Why did we win? I'm so amazing. You know, but the truth is, you know, when you get someone independently to say, look, you spent the last however many months evaluating this company, will you spend 30 minutes so that they can get better? Most of your prospects are willing to talk to someone about it and they're really happy to give you the honest truth about, you know, sometimes it's no, your price was actually cheaper than everyone else's and that made us skeptical that you knew what you were doing. Or maybe they're giving you that shot between the eyes about, you know, your sales. I had a sales team that, you know, the feedback was constantly, they're really aggressive. It feels like used car salesmen. Yeah, great. I'm glad I learned that, you know, now now we can move on forward and, and course correct.

Thanks again for listening to the CRO Spotlight Podcast. We're excited about all the great guests we have, and more importantly, we're excited mostly about you for being avid listeners and supporting the work that we do here. Feel free, please, to share the CRO Spotlight Podcast with any of your colleagues. We just think there's a great wealth of information here and we want to get the word out to as many people as possible, and your, your support of the show is really appreciated. I wanted to share information about a program that we offer called the CRO Masters Council. The CRO Masters Council is a bimonthly group of 6 seasoned Chief Revenue Officers who are looking for a Chief Revenue Officer board of directors, so to speak, that they could share what's going on with them, collaborate with ideas, get some feedback on what's going on in their current role. And these are great conversations. I facilitate them. The CRO Masters Councils, again, they're twice a month and they last for at least 6 months to a year. So if you're interested in having your own CRO suite, your own board of directors of Chief Revenue Officers, it's a private confidential conversation that we have. It's infinitely useful. Imagine having a room full of other Chief Revenue Officers you can talk to and say, hey, I'm working on this, or have you guys figured that out? Or I'm having this issue right now with my business or my results. These are just invaluable conversations with Chief Revenue Officers. Chief Revenue Officers have a very, very unique role. It's a very lonely job and only other CROs understand what you're going through. So that's why we created this program. So if you're interested in being a member of the next CRO Masters Council, which we have a number of them being put together right now, just go to my LinkedIn and DM me Masters or Masters Council, and I'll follow up with you and set up a call or send you some more information about it. Looking forward to seeing you there. And thank you. Yeah. I think talking to prospects, customers is vital. And I don't think that CROs do it enough. It's— that's the— that's where all the gold is right there, you know. Why didn't you buy us, right? Like, why did you churn? You know, what happened? Um, and you can pick it up in signals, but having these direct conversations, I, I think that's the gold. It's right there. I think the CRO's job is to have as many of those conversations as possible, if I'm not— if I'd be so bold, you know.

Um, well, and I think it's getting easier for us now, you know. I'm actually just about to launch the next book, which is The AI Handbook in for sales professionals. No, yeah, but, you know, now we have, you know, all of our calls are recorded on Gong or Clari or, you know, whatever, whatever your tool is. And so it gives us this huge data set that's immediately mineable for, you know, what's going on with this particular salesperson on all of their calls, what's going on with this particular competitor. And AI is really good at data processing. So, you know, today's CRO doesn't have to really sit down on every single interview or spend a ton of money outside because if they use a tool properly, you know, they can start to surface all of those insights and literally be in the room with every seller and every customer, every sales call that we're on.

Yeah, let's talk about that. I was going to talk about it a little bit, but we'll get into it now that you brought it up. So I'm hearing stories now, and I think it's probably true. That, you know, companies, when they interview a chief revenue officer candidate, they want them to vibe code, like build something for us, show us what you're capable of, right? I'm seeing this, and I think it makes sense. I mean, these skills are vitally important. You know, you need to be able to know how to do it and how to make it work and also know how to roll it out across an organization because it's vitally important now that someone who's running an entire revenue organization needs to have, you know, a kind of a facile ability to use this stuff. What are your thoughts on this? And what do you think is happening? What's the— is the profile of the CRO completely changing? And what's the future, like the 2027 CRO look like in your view?

So some of this reminds me of coming out of school in the '90s. As you know, I was one of the first classes of college graduates who had email addresses, and we went into a workforce where—

you and I are probably the same age. Yeah.

All of a sudden, you know, like literally my first office was sending things around in manila envelopes with string tied around them. And, you know, the entry level, you know, new hires were emailing each other. And there was a lot of business that we didn't understand, but we also kind of leapfrogged some of our more senior colleagues because we're familiar with email and how to use the web and stuff like that. I think we're going to see a similar trend with AI that, you you know, a younger generation is coming out digitally, you know, native. They know how to use these things and they're gonna get great results. I think as leaders, you know, we have a lot of perspective on strategy and business context and understanding that they don't necessarily have.

That's true. Yep.

So I think the CRO of the future, you know, really needs to, you know, to learn about AI to stay relevant. Because they will be replaced in 2 or 3 years if they completely ignore it. But they also need to kind of double down on what is their unique skill set. And I talk about this in the book, that it's, you know, for salespeople, it's the core humanity things. It's for the sales leaders, it's inspiration for sellers, it's trust building and empathy and perspective taking. And you can't prompt, you know, an AI bot to go empathize and develop trust and build a relationship with folks. You can prompt a bot to prep you for all of those calls. So if you and I are gonna go to dinner, you know, a bot can sure find out everything that's knowable about you and inform me so that I'm more educated when I sit there. So I think the CRO of the future is really gonna be doing both of these things is, you know, understanding tools, understanding what makes sales work, and then putting those two together.

I agree completely. I think that, we're seeing this almost strange need for more humanity now. We run these events and people love them. They scramble to them. They want to be around humans. And, I think that what we're hearing, because I speak to everybody, is that the main attraction is just— I think people are really tired of speaking into machines and looking at machines all day. And, You're correct that as we get a bit more mature in our careers, it's those unique skill sets that are gonna become accentuated. They're not gonna become buried. They're gonna be important and vital, but you have to know what those are. I think that people have to really kind of figure out like what their really good soft skills are and how they're unique and how they make their jobs important and how they fit into the job. Like I think the good news is in communications-related roles like CROs and sales, those things are inherent. Like you're talking to people, it's obvious, right? And there are other things where it's not so clear. I mean, engineers, I think, are gonna have a really tough time with this, but I agree. I think that you're, you're not gonna go away. However, I'm curious what your thoughts are on things like consulting, you know, and strategy and development. I mean, how much is that gonna be stripped out in your view? I mean, I'm sure you see a lot of people utilizing these tools to build like McKinsey models, et cetera, et cetera. We're doing it and some of them are really impressive. How much of this is, I know it's hard to answer, but I'm just curious in your, you're looking at PE companies, how are they managing this and what's their thoughts on how they're projecting outwards when they look at people?

So, I think the consulting firm of the past used to hire, you know, 200, 300 college graduates every year and put them to work on data analysis tasks, assemble these spreadsheets, run these analyses, put them together in the PowerPoint. And, you know, after you had a year or 2 years, but 3 years of that, And one, a bunch of those, those 200 kids attrited and went on to something else, but a handful of them developed really smart skills and survived. And then they became, you know, the, the analysts and the insight folks. I think now, you know, this management philosophy of delegate the work to the lowest cost resource, you know, that lowest cost resource is not a fresh college grad. It's, it's going to be an AI bot. And so I don't think those consulting companies are going to have to hire 400 college grads. They might hire 25, they might hire 50 who are going to use tools to do all that kind of data analysis. And then I think the trick is really going to be, you know, how do you give them enough real-world experience that they can move past the analysis stage to really the consulting and advising? And I think salespeople see this in the SDR ranks as well. You know, here in Chicago, we had, you know, CDW and Echo Logistics and all of these people would hire these bullpens of sellers to just, you know, pound the phones and dial 100 times. And, you know, by the end of the summer, you know, the final few survived and then you had some really good salespeople. You know, today they probably don't need to hire all of those, those kids that we're going to churn. But the handful that we do are going to have AI tools and have the data at their fingertips. They're probably going to have more conversations. And so they're going to actually be in more sales opportunities. In a short window of time, or at least more customer-facing opportunities in a short window of time. And then it's, it's going to be these soft skills about persuasion, perspective-taking, empathy, trust. That's really what they're going to have to learn to put in a business context and move them to the next level.

Yep. So, uh, right now you advise 36 portfolio companies at Five Arrows, right?

Uh, that's the whole portfolio, and technically any one of them might tap me at any time. I'm working with—

technically you advise them when, when needed, right? You're on call model, right?

Exactly.

So I'm, yeah, I'm curious, like, what your thoughts are. Do you think how many of those 36 companies are ready for a CRO, or were ready when they hired one?

Well, I mean, one of the things I love about the Rothschild family is that they're pretty good investors. They've been doing it for a long time. And so we're pretty specific. And maybe this is your earlier point about, you know, people have a model. We don't invest in just anyone. We don't buy any company. You know, back to my house flipping analogy, maybe we're really good at kitchens and we don't buy any houses that need new roofs. And so I think, I think in our portfolio, most of the companies that we're working with at that $50,000 mark, which is sort of the lower end of, of one of our funds, it's the first CRO they're getting, you know, are they ready for it? You know, financially you would say yes. Culturally, there's a lot of dynamics and that's, that's why I have a job is to help you work through that because we're either elevating a VP of sale to a CRO or we're working with that executive team to explain why that's not a good move and we should go outside. And then you have all of the kind of cultural change management things of, you know, just because you've done it this way for 20 years, you know, now here's an exciting new playbook that's going to, you on my growth for you going forward.

Gotcha. So let's talk a bit about the book. It was really great. I mean, it's really smart. And if you don't mind, just lay out a couple of key frameworks from the book that you want people to think about when they're looking into reading it.

Yeah. Well, so the new book is all about AI. I started because I wanted to have relevance in this kind of brand new frontier. And so I began by interviewing, you know, all of the CROs in our portfolio and asked, what are you doing with AI and sales? That then led me to a set of 158 different tech tools out there that say, I'm an AI tool for salespeople. And so I evaluated all of those as well to really figure out, you know, what's hype and what's real. The conclusions I came to is this bit about AI is a really good pattern recognizer and processor of data. It is not good at humanity. And sometimes because the computing power lets you process at scale, it might look like it's a human. So, you know, it knows that when I say I'm having a bad day, statistically you're supposed to say, I'm so sorry. I hope tomorrow gets better, but it doesn't really understand that. And so, you know, the trick with AI tools is how do we really figure out, you know, what are the core human elements that we have to keep salespeople in? What are the, you know, drudgery things that salespeople are doing that is not sales time? You know, Salesforce has a study out, their state of sales says 72% of our time is not selling activities like, oh my God, I'm sitting in list building. And if we get good at that, I think that kind of guides us on what tools should we use and when should we use them.

Which ones do you like? I'm sorry, I'm curious which tools you're looking at and like right now.

I'm sorry, I interrupted you. Oh gosh. You know, I know this is a market that's going to change really fast.

Sure. I'm just curious, like as today and like maybe even you can maybe be as specific as possible, even more directionally, like which ones you think are good and also are going in a direction you think seems to seem to have legs in terms of how it's going to look. I'm just curious. I know you're being a bit of a prognosticator here, but I'm interested in your perspective on it.

Yeah. Well, I'm going to start first and tell you a story about where I've gotten it wrong. You know, that very first startup job, I worked with the founder that, you know, did really well with, with, you know, the web content management we were selling. And then he went on to found another company where he told me, you know, I'm going to go change the UI to your computer so you can go talk to it. And I said, that sounds really stupid. There's no way I'm going to follow you. Well, Tom Gerber went and founded a company that he called Siri. And so we'll start by saying, you know, we'll start by saying I'm not good at picking.

Okay, fair enough.

But I actually think, I actually think the interesting categories are the ones that are allowing me to show up more authentically human in all of my interactions. So I really love the categories of tools that are saying, here's how to pull together all kinds of prospect research and put it in front of you. I like the categories of tools that say, as we're having this conversation, you know, I'm hearing this body language and this suggestion from Warren that, He feels passionately about this or not, or he didn't really respond to what you said last and give me those prompts. Yeah. I'm not as big a fan of actually, you know, handing over the reins to tools that are going to run all of these, these things completely.

You mean sort of like a Cluey or one of those sort of things that in real time can help you make sort of observations and things like that, like that sort of thing?

Yeah. I mean, there's a, there's a ton of them right now. I think they'll eventually be integrated in our Zoom tools or whatever we're using.

I see. Right.

So I think all of those kinds of coaching tools that, that process data and give us signals, I think are great. There's a lot of hype around agentic AI and we're going to have no salespeople or we're going to have, you know, these bots that are going to have the first 5 emails with you and, you know, then going to negotiate the contract and, you know, just a handful of people are going to come in at the very end and sign the contracts.

Yeah.

I don't think we're really there yet. And I'm not sure, you know, to your earlier point, I see a lot of sellers right now going back to old school face-to-face meetings or let's get 7 people for dinner at a steakhouse in Chicago and talk business.

I was invited to a basketball game. I haven't been invited to a basketball game in years, you know, and it was like, okay, this is old school. I like this. Yeah.

Yeah. But the other takeaway I got from the research is Um, this is a place that the legal landscape is really evolved faster than I was necessarily aware. You know, I first really started to think about AI when ChatGPT burst on the scene in November of '22. And of course it's been around for a long time, but I think that's when a lot of people, you know, just 3 years ago, 4 years ago, started to think about this. And, you know, the data says that like only 1 in 5 American workers is actually using AI in their, in their jobs today. And so a lot of them are thinking like, oh, it's something that'll make a cute video of my dog or write a haiku or things like that. What's actually happened, and of course Europe is really forward leaning on this, you know, they already have an AI act that talks about, you know, what kind of data can you be listening to and how do you process it? When do you have to disclose, you know, that you're talking to a bot and all of these things. And then in the US, we have all these patchworks of legislation and and regulations that say, you know, can I have AI make a job offer? Can I have AI, you know, evaluate a seller? You know, at what point in the negotiation process, you know, am I stuck with whatever terms it negotiated? And so I think that's a landscape too for the future CRO is really someone who's going to partner with your HR team on cultural issues, your chief legal officer on legal issues, and then kind of all of the ethics of, You know, probably if it doesn't feel right, you shouldn't be doing it. Um, right.

Uh-huh.

You know, kind of where the law is following us as well.

That's great. Uh, I look forward to it. Uh, when's it coming out?

April 14th.

All right, great. Well, uh, we'll be looking forward to it. Uh, I appreciate you coming. As I expected, this is a great conversation. You certainly have a wealth of knowledge. And again, uh, thank you so much for being here. I have one more follow-up question for you before, uh, you go, and that is, um, What do the people who work for you tolerate about you?

You know, I work in a job that's supposed to be very extroverted, but actually I'm an introvert and I get very— as much as I talk about humanity and technology and the intersection of humanity, I will get tripped up on very interpersonal kinds of things. And so my teams always tolerate that actually I do need to be reminded a couple of times about like, what was your dog's name? How old is your kid? And that sometimes I have to be very intentional about cultivating those personal relationships.

Got it. Well, cool. Well, look, again, I appreciate it. It was really great talking with you and thanks for joining and I'll see you soon.

Thanks for having me. It's always great to see you.

Thank you for listening to the CRO Spotlight podcast. The CRO Collective's mission is to help CROs succeed and help founders and CEOs build CRO-ready organizations. You can find out more information about our services at thecrocollective.com. That's thecrocollective.com. And we look forward to having you join us next time.