The Fractional CRO Debate & Getting Sh!t Done with Neil Weitzman

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 freeform 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. Welcome to this episode of the CRO Spotlight Podcast. This is Warren Zenna. I'm the founder of the CRO Collective. And, you know, I had a really interesting, I wouldn't say debate, but interesting little disagreement with a really smart guy on LinkedIn like a month or so ago about, you know, the fractional CRO thing, which, you know, I'm a big pain in the ass about all the time. And it was just a really smart conversation. Like I usually do, I said, well, let's debate it on my podcast. He said, sure. So I was really glad because I've heard of Neil Weitzman before many times. We sort of like are LinkedIn buddies in a way. But, you know, we never actually met. So Neil, I'm real thrilled to have you here. I know we have a lot to talk about and I read a lot of your stuff and I follow your, all your content. So, uh, welcome and thanks for being here.

Uh, thank you. I am honored to be here. It is great to meet you in person on the Zoom call here at Riverside. Um, but thank you for having me. It's a pleasure and I can't wait to argue and debate with you.

Tell me a bit more. I know a lot about you already, but tell my listeners, whom are mostly chief revenue officers and aspiring chief revenue officers and go-to-market leaders. So you were at Nielsen for like an entire generation. Like you were almost there, like 5 children could have been born the time you were there, you know? And then you left and then you were a CRO for a really short period of time and you said, screw this. So I'm just curious, like walk me through how this corporate, long corporate gig sort of set you up for where you ended up.

Yeah. And I love the way you say for a generation is a polite way of saying, Jesus hell, you're old.

Me too. You and I are both old. We're both crusty. So believe me, I'm talking to myself right now.

Yeah. Yeah. I was at Nielsen for a long time. That's where I started my career. I loved it. And I feel like aside from the labels and titles that are out there that are often very misleading depending on the company, the role in the industry, that I've been a sales leader and GTM leader for much longer than a title would dictate. Of course, it differs by industry. Some of the industries I came from don't use titles like that, but that doesn't mean you're not doing the same job essentially.

100%.

Yeah. So, so I've been a leader in sales, marketing, you know, RevOps, etc. for many, many, many years. But yes, I've only held the official title in the B2B world for a shorter period of time. Before I did leave, if you will, the full-time CRO world and start my own company called Weitzman GTM, where I do GTM advisory. And as I will define it later, we'll debate it later, fractional CRO work. But I love it. It's my most exciting part of my career. And I get pumped every day that I get the honor of working with CEOs and founders to help them build their business.

Great. I love it. So you go to market or what, get the fuck out? Is that basically what it is, kind of, right?

I think you're referring to my aptly named newsletter, GTM or GTFO. Yes. Yeah.

Right. So what were you reacting against with that? Like, what's the context? I don't disagree with it, but I'm sort of curious as to like where that drove. Obviously, some provocation must have had you want to make that claim.

I think I mean, to be fair, I was having a little bit of fun with labeling and marketing. But without a doubt, I do believe, as you know, many of us have talked about over the last couple of years, especially that go-to-market and, you know, being a chief revenue officer and leading business and revenue in many ways is harder than it's ever been. And that said, the bar is quite low on what I think good GTM looks like. Um, and we could talk about that, but yeah, you know, there's so much crap out there. And so the idea, of course, is like, if we can just be elite at GTM, um, then, you know, the world's your oyster, right? If you could just be better than 99% of the crap out there that we see, you're probably going to be okay, even though GTM is incredibly hard.

Yeah, I agree. I'm curious to know what your thoughts are on this though, because I agree. Why? Like, why is it that with all the knowledge that we've accumulated for the last, let's say, okay, 30 years, let's say about what we call go-to-market, which I also find a really strange term to be frank with you. I kind of weird that we use it, but we do. So fine. Why is it that this sort of revenue generation or revenue growth or revenue expansion, however, however you want to refer to it, is so messed up? Like, why is it that regardless of the amount of information and experts— and I speak to so many people who are so smart about this— companies still keep doing the same thing? What's your prognosis on that? Is it no different than, like, diets? Like, we all know what to eat right now, but we don't, right? So what is the reason, do you think, why it's so messed up?

Yeah, I think we get caught up in this echo chamber. I think it's really messed up in many stages and sectors of business and industry and not nearly as much in others. If you took, you know, I'll just make up a number here, the top 200 large B2B SaaS AI companies that were, you know, hundreds of millions, billions, I don't think we would say they're as messed up without a doubt. I think it's the other 90% that may not be as big or mature from a GTM perspective. But they're the ones that we see so much shit and noise from and still spamming and still all the crap we see that's out there. And from a quantity perspective, it's like that. And it looks like that on LinkedIn, many of us see. So I feel like a lot of it is echo chamber. I'm sure either one of us can point to lots of companies that are doing incredible things really, really well. There's just sadly too many, especially early stage Startups, founders who think they know what they're doing and don't go to someone they trust. And yeah, it's just, there's a lot of shit out there and a lot of it does come from the startup world where people think they know what to do. And, you know, founders who come from worlds that are not GTM but still think they know the answers and then they just start going and doing stuff because someone somewhere told them to go email 500 freaking people at once.

Right. So you think it's more sort of like you said it like an echo chamber. Uh, I, I, I agree. I do think there is sort of some codification of, you know, this is just the way things are done, you know, in a weird way. Uh, I sort of look at it like, um, businesses are, are like humans in that the way that we develop organisms are. Inherently immature for a very long period of time. And even with good parents and good environments, there's certainly no question that more strenuous environments make kids grow up faster. But generally speaking, it still takes time. They don't come out of the womb knowing how to do a lot of stuff and they still don't make really good decisions even when the data around them shows them otherwise. I mean, I was a kid. I made a lot of really dumb decisions because I just wanted to, you know, and I do think that, you know, why it is that all of us, when we grow up, we ultimately find ourselves saying, wow, my parents were really right. You know, they're saying like, well, you know, if you figure that out 20 years ago, you'd be a lot further along. And, you know, it's exhausting to hear you say that to me right now. I feel the same way about one of our clients. I'm like, you know, you probably had known this stuff, right? I mean, is this a surprise to you, any of these things? So, you know, I could get into it, but I asked the question because where we go to work is a lot of that stuff, right? We're trying to figure out What are the dynamics that impact the way organizations are structured and the firefighting and the politicking and the structural components of a business? And how do you accelerate the learning so that people get things done faster? Where is it that you find you enter the market? What's your client profile? What size are they mostly?

Yeah. And it's a great topic. Most of my clients would range from 2 million to 25 million ARR type of size. Uh, so let's call that generally teenagers.

Teenagers.

Yeah. Pretty early stage.

Yeah. Just to keep it straight. They're adolescents. They're, they're post-adolescent. The CEO is still the person that probably founded the company, right?

In most cases. Yeah.

Most cases, right?

Yeah.

So like you said, they're, they're like in that sort of, you know, pupa stage, maybe the first or second time. And I get it. I mean, I've worked with this stuff and, you know, what you're doing is you're, I assume you're trying to kind of accelerate their thinking so that the mistakes that they're going to make in the next $20 million, they don't make because they make, they learn the lesson now in a way, right?

Yeah. My job as a, let's just use the word fractional CRO for a moment, is in my opinion, as much about helping depending on who it is, but let's say the average CEO founder to be a better CEO founder from a GTM perspective and coaching them as it is about doing traditional kind of CRO work. I spend a lot of my time politely and sometimes very passionately debating and arguing things with them. And sometimes they listen and sometimes they don't. And I'm not right all the time either by any means.

Sure, I understand.

Sure. But, you know, quite often I do a decent job and I am right and they don't believe me.

Just the same as like it made sense that my parents were right about a lot of things, you know, they just were, you know. And so, okay, that's interesting. So that actually helps frame it because, you know, again, I'm not, this is not intended to be by comparison, but just so that we're framing the way we talk to each other. My clients tend to be more post-25, 30 million. For various reasons, which will, might in fact actually have us agree on a lot more because of that, but that's, we'll get into it. So I just, I'm curious about something. So you were a chief revenue officer at RIWI, right? Was it RIWI or R-I-W-I, right? And you were there for a very short period of time and then you left. And what happened? Like, what was it? Did you, was it like, this sucks, I don't want to be here anymore? Was it, I had enough of this? Like, what was it that happened?

Yeah. Well, without getting Too personal.

No, no, I'm just curious because you were there for a period of time and that was when you were there.

Yeah, I was not there for a long time. We parted ways, me and that company, when literally March 2020, which I believe was COVID. One of the first real months where everyone was like, go home, no one's coming to work.

Yeah.

Yeah. So we did part ways for various reasons and it had some some bearing on what was going on in the world. But what, what triggered for me, irrelevant of that situation, sure, sure, was I guess the spot I was in my life and career. I was kind of like, I've had enough of this stuff. And to each their own. Everyone's got to decide for themselves 100%. But I was, I wasn't 20 anymore. And I had said, I've gone through this kind of situation too many times in my opinion. And, you know, it was only a couple in my career to part ways with a company like that. But I didn't love the feeling. And even though, even though I felt very confident in my abilities and my success that I've had, that doesn't mean everyone agrees. And, you know, irrelevant of how good I think I am, if my boss doesn't necessarily agree, you know, it's not going to work. Work out. And I was kind of just had enough of that, Warren. And I just felt like I'd rather control my own destiny. And I know enough to be able to do that. And it took me a little bit to get my head wrapped around it. But I said, enough of this. I'm going to go build my own business and control my own destiny. And I'm super, super grateful I did. It's the most fun I've ever had. It's been the most success I've ever had. And I love it.

It's great. I love it. I mean, similar, right? I think there is a, uh, what we deal with a lot of chief revenue officer officers who, uh, go through the trials and tribulations of these jobs and, you know, the emotional damage it does to, to people. Um, and, you know, the successes too. I've seen some people have amazing experiences, like just really great But, you know, so many things have to be in place for that to happen. And all too often they're not. And so, you know, our point of view is, and to, to kind of reflect on a conversation I had with another guest on this podcast, he was sharing about an experience that he had in the past. And it's always interesting, the entrepreneurs all say this sort of thing is, you know, having been like punched in the face too many times, I finally decided I didn't want to participate. So my reaction to that was, and this has more to do with the way that I'm looking at things now that I've started doing this as long as I have, is that, and I told him this and I feel the same way about myself, and he punched himself in the face. And here's what I mean is that similarly in the way that you and I just talked about why it is that people keep doing the same things, I think executives do the same things too. Like they take jobs where they clearly can see and detect things aren't going to work about it, but they take the job anyway and they sort of hope it'll work out. Where they'll figure it out, or maybe they're wrong, or they're being too picky, or they don't want to be difficult, or they don't want to lose the opportunity. And all sorts of rationalizations why they kind of end up in situations where they're like, you know, I kind of knew this was going to suck. So they did punch themselves in the face. And the second part of it is, it's not just like avoiding things. It's also having the ability to know how to actually have an impact on those things that you can change them before you take the job. And so we took, we do a lot of this work people because again, in the role that we're helping people in that post $25, $30 million range, you know, you're now part of, if not the builder of an engine that you need to have things in place properly, or you're not going to succeed. And those things can be pretty clearly defined. So those people, like, unlike you and me who go, I'm going to do my own thing. Some people don't know how to do their own thing. They don't really have that sort of personality. It's not an easy thing to do. You know, and so what they do is they keep getting jobs because that's the place where they're going to make their money. And I, again, I have no issue with it. I think it's completely honorable thing, but if you're not an entrepreneur and you don't have the kind of personality or constitution to go out and do your own thing, you've got to become a different type of animal to be able to make it work. And that's the shift you have to make. And so this is sort of like where I'm interested in. A fractional, let's call it that, someone who comes along at an earlier stage, what you do, given that context, is actually 100% appropriate because that's exactly what they need at that stage is somebody like you. They don't, they shouldn't have somebody—

Very stage-specific.

100%. 100%. And that's that adolescent pupa stage where they need some really smart person to come in. They probably could never afford to hire you full-time and you'd never do it anyway. And they pay you a decent amount of money every month to say, all right, bring us some maturity, you know, get us where we need to be.

Not nearly enough money for the record, should be way more.

So walk me through, you must have a methodology, an approach, that kind of thing. So when you get engagement, like what sort of way do you view the world, their world, so that you can have an impact on them?

Yeah. And I want to answer that. I also just want to reflect on something you said that You know, even in that my latest full-time CRO job, I made that mistake. I punched myself in the face.

Everyone does.

I could reflect back and say, how did this end up how it ended up? And without a doubt, 90% of the problem wasn't anyone else. It was my fault. It was during the interview process. I was excited about the opportunity. I got ahead of myself. I did not ask anywhere close to the right level or detailed questions. And had I done that, I would have learned so much more that probably would have said, so this isn't the right job for you, Neil.

Or if you want it to be the right job, here's what I need it to look like and then I'll do the job. And they might have said, you know, okay, that sounds right. And then you have a job, right?

That's the difference. Yeah. So I just wanted to reflect on that because you're totally right. You're totally right. Yep. In terms of, you know, my process, maybe unlike some other people that, you know, colleagues and people who compete with me in this space. I don't have a set consistent, here's exactly the master playbook and here's exactly what I do every single time. I actually think that's kind of bullshit.

Okay.

I do believe, of course, there's a lot of the same elements that you have to cover off. Yeah. Without a doubt, we need to make sure, for example, you know, the cliché most like, where do you start? Well, What's your ICP? What are we focused on? You know, are we really focused on the right ICP and who the buyer personas are? Do we understand what good looks like related to that? What kind of process do we have in place around qualification of people like that? How it comes into the system? So all of these things are, you know, the beginning of understanding from a diagnostic process to say, hey, you know, the CEO brings me in. And this usually happens to some degree in the interview process, at least the initial elements of the beginning of a diagnostic, where I ask all these questions to see if it's even a fit for me and if they need me is, do you have these things in place? Do you have it documented? Oh, it's all in my head. You know, everyone knows in the company what this is and they all know what to do. I'm like, really? You know, we go through all these different questions and it helps me understand, is there improvements that I can make if I was to join, you know, the team on a fractional basis. Yeah. And then we go through it and I have a list of like 30 different, let's call them GTM elements that we need to go through. You know, everything from ICP and buyer persona work to what's our sales narrative and what's the elevator story? What's our messaging? You know, what is the right GTM motions in the first place in terms of outbound and inbound? And we go through it full, full, you know, soup to nuts all the way through. And some of it is, hey, it's in pretty good shape. Good job. You know, I don't see anything that I can make a big adjustment here. And others, it's, yeah, I see some clear gaps or some, you know, from my experience, some things I would like to change with you. And then we'll work through that very hands-on. And other times I'll suggest things like, Hey, I don't know the right answer here, but what you're doing isn't working very well. So let's run a few experiments and make sure we set them up in the right way. And so, you know, you've been a CRO many times. Yeah. Same type of thinking of that. Like, if I know what to do, I'll say it, you know, and if I don't know, then I'll suggest that we should run some tests and experiments properly. Yeah. To see where we should double down versus optimize and so on.

Hey everyone, I want to thank you again for listening. I get great comments across LinkedIn and other channels about the show, and it's really gratifying to see that we're having an impact on you. Another thing I wanted to let everybody know is that we also produce events. About 2 and a half years ago, we started these CRO Roundtables predicated on the idea that— well, two premises. One is CROs are looking for other CROs to talk to, which is really true. It's a very lonely job. And how do we get a bunch of CROs in a room where they're not being, let's say, disintermediated by panel discussions and sponsorship events and demos and stuff, and really give them a chance to talk to each other? So we created a roundtable event that is essentially that. It's a 3.5, 4-hour discussion between between 20 and 30 chief revenue officers, and these are amazing events. The format took off, people love them, and I get requests all the time as to when is your next CRO event. So to that end, I just want to let you all know that we have a number of roundtables coming up over the next year, over the next, like, 2026. I want to share them with you so you can, if they're in your market, you can come. So the next one we're having is going to be in London, actually, in February, February 24th in London. So if you happen to be a chief revenue officer in the UK or even in Europe and you want to come by, you'll be hearing about it more on my website and my— and LinkedIn, but put it on your calendar. And then following that, we're probably going to be doing an event in San Francisco in March. There's going to be one in New York in March. I'm going to do another one in Chicago probably in April. And then I'm going to do an event in Boston I'll do an event in Atlanta. I'm going to do an event in Salt Lake City. I'm going to do an event in Austin, and I'm going to do an event in Los Angeles or the Southern California area. So those dates are to be determined, but they'll be going across all, all next year. And these events are taking on huge momentum. They're the place to be if you're a chief revenue officer and you want to be in a room with no interruptions and have an opportunity to really share with each other in a sort of a private and confidential open discussion about everything that you want to talk about as a chief revenue officer and collaborate with great people. So thank you and thanks for supporting the show. And I look forward to seeing you at the events. Got it. So, you know, I just really, I think you said something I love to dig into because I agree with you. And that is, okay. You know, I ask about a process because you sort of have to, right? And the reason is because brains need a way to frame things because without a frame, it's just a blob and they can't grab it. Right? So, you know, everyone has a framework and you need one, but I agree with you. I think a framework or a process is, if I may, it is a way in which a, our, your, my particular expertise area of expertise can, we can bring to bear on your organization, right? It's just a framework through which we can bring our expertise to bear in your business. Whatever that might be. So how would you define yours? Is it more like you're data-driven or you're more process-driven? Are you looking at things more holistically? Like if you were to sort of try to articulate your philosophy, right? How would you say that Weitzman philosophy sounds like differently from somebody else's?

Yeah. Oh, wow. You're really teaching me here. I would say without a doubt, process and data-driven. So I believe Everything needs to be built out in the right way. What is— what do we understand how to be consistent on? Now, you can't build a process till we understand what works. So we might have to test different things, but ultimately our goal is to be able to figure out what works or what good looks like so that it can become a consistent process that we can follow. The one difference I would say between me and you know, many people that I come across without sounding okay. Um, let me put it this way. The, the reason I win the deals I win is because of a very clear ability. And just like I said, my website to execute and get shit done. Um, I feel that my attitude and my approach to working closely with CRs is CEOs, especially and specifically at the early stages where founders are about executing and getting shit done as quickly as possible.

No question.

Aligns really, really, really, really well. And the deals I win, they usually say it's because of that point versus a competitor of mine that might have been much, you know, great in their own right, but much more about more of a consultative advisory approach as opposed to getting their hands dirty and getting shit done. And for me, for me, that's what it is, is I, and I position it. If you were the CEO, Warren, my approach to you would be, Warren, I am your partner. I want you to think of me the same as you do as a full-time CRO. I'm going to do everything they do. I'm going to work. As hard as I can to get shit done and move this business forward. The only real difference is that I'm not full-time.

Gotcha. So, so given that, again, that goes to the earlier point that I was making in our original LinkedIn conversation is how much time can you devote to it if you have a whole bunch of clients? So I'm just curious how you manage that because that, that's where some of this stuff I see, I have a lot of colleagues who are in the business you're in and they get to a point where I just can't, I just can't do this anymore. It's just too, too much. And if I really were to do the job that I need to do for a lot of my clients, I need to spend more time with them and I can't because they're not paying me enough to do that. So the scalability is not there. I'm just curious what's the way you navigate that problem?

Yeah, that's the hardest part for sure, Warren. And especially for me, I'm a, I really get really passionate about my founders and clients I work with. So it's very hard for me to like turn it off and not give them more time than the time we've agreed.

Sure.

Just because it's my attitude, it's who I am. That's my biggest weakness is how do I manage that knowing what I'm like? Yeah. But the reality is it's in my control, right? I mean, any CEO who I work with is grateful if I want to give them more time, of course. So they don't have a problem with it. It's my ability to manage it, to keep a sanity about me. Generally, my engagements are they're not time-based so much, but there is like a sense to that.

Sure.

So generally my packages are kind of like approximately a day a week or approximately 2 days a week, which means, of course, you know, 3-ish clients is like the maximum I should kind of be taking on without going absolutely crazy. And that's the way for— I try to think about it.

Okay.

I mean, even if they're a day a week-ish, 3 clients in a day a week, some people will say, well, you've got 2 more days. Well, the reality is when you're jumping around client to client, it's much harder. And I, like any good salesperson, I need to leave time for building my own brand and my own business development work. Yes, sir.

You do. But I did what you did for a while, quite a while. So I understand exactly what you're saying. I went through this problem because I too, I'm like you. I tend to say yes. I want to help people. Yeah, I get into it, you know, it's sort of like turn the spigot off. In fact, here, even here, I have people I work with now in my company, like, Warren, you're talking to too many people. Just be a little bit unavailable. It's totally fine. You know, but, you know, I try to like talking to people. Someone asked me a question. I want to answer the question, you know, exactly. You know, I feel like a little boy a lot of times that way, but it's not necessarily a good thing. So there's that balance, right? There's Neil's business and Neil's expansion and Neil's scale. And then there's the client getting what they're paying for and not surely understanding how they're supposed to buy something they never bought before. Like, how does this work exactly? Like, how do you measure results? How do you, how do the clients know that aside from the obvious, which is I'm making more money, but just the minutia, like the day-to-day ways in which clients know aside from I'm getting attention from Neil. Do I know that Neil is actually making a difference for me and the impact? What are the impact metrics that you know you can count on to make sure the client sees value?

Yeah, I mean, every client, I mean, there's some similarities, but they're all a little different too, right? Like, for example, I had a recent client who one of their biggest issues is they were trying to do a better job on their outbound. And it was all about, to some degree, it was cultural. But to some degree, it was they just didn't know what good looks like and they weren't trying the things that many people in modern-day 2026 go-to-market are doing well. And so, aside from the metrics, it was a real simple approach to look at their data and say, wow, you're not getting any responses from your emails and your cold calls and all of the things you're doing. And I can quickly identify, you know, why I think that is. And then we implemented very simple, let's try some video and some voice within your outbound approach to make it more human. And literally within 2 weeks, I was getting messages, oh my God, one of the biggest clients and prospects responded to me after 3 months of not responding. And so aside from all the data, when, you know, just that type of evidence, there is like You know, it makes me— it makes me feel great because the reality is it was a real simple fix. It was just they didn't know what they didn't know. Like, no one was not trying. And we were, of course, able to quickly see that based on that, the pipeline quickly started to get a little bit better every day because you can't drive pipeline if you can't get responses and actually talk to people. Yeah. So, you know, very simple example there. The one thing I'd point out, Warren, is You know, I said in a very flippant way before that my job as a fractional CRO is essentially the same as a real CRO, a full-time CRO, but just part-time. There is a couple nuances, of course. And one of the nuances is it is hard to hold me accountable to a metric when I'm not there full-time. Yep. And I've had some CEOs say, well, Neil, if I'm going to pay you X, then you need to guarantee me that you're going to get X amount more pipeline. And my answer will be, I'm going to do my best. And I feel pretty confident that I'm going to influence change and growth, but I'm not willing to be measured on that type of success and accountability. I'm just not. If you're going to say, Neil, you pass or fail based on hitting this number, I can't take that on. And you shouldn't want me to, right? Because I'm not there all the time. I'm not going to be able to be involved and jump on the client calls like a full-time CRO might do. Of course, I'm not able to coach the team whenever they need it all the time, 24/7. So there is certain things. So it's not fair to me and it's not fair for me to say yes to be accountable to a number that I truly 100% can't own being in a part-time role. No, it doesn't mean I can't affect change and make a difference.

Sure.

They're two different things.

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 want to get the word out to as many people as possible in 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. No, no question. And that's, I think, the point of where we're really the nexus of what we're talking about. Is the fact that, but that's a pretty big compromise for a lot of people to make. Right. I mean, if I'm a founder, you and I know this better than most.

Yeah.

Those are precious dollars they're giving to you. Right. I mean, they're, they're, they're carving up that budget and they're giving me a nice amount of money for like, this has got to do something for me. And there may be someone who's holding that CEO accountable for that money, you know, because there always is somebody. And so you're saying to them, which I, I understand. Like, here's the, like, it, like, here's the limitation on what this is going to get you based on just the dynamics of the relationship, right? I'm not there all the time. And therefore I can't be held to account in the way that you would if I was there full time.

Yeah. There's a key difference though.

Yeah.

Um, that I think is to let's like go back to stage specific, meaning, meaning in very early stages. Often the number one need is less. I mean, everyone wants pipeline all the time, of course. Give me more leads, more pipeline. I don't care how big you are. That's always the number one thing. But in early stages, generally I'm brought in because they need a foundational GTM process system, tech stack, handoffs, team, everything built out. So it's as much about as a building initiative as it is an optimizing initiative.

Look, I agree.

Yeah.

That, that's what it should be. But the thing I see happen is that's not what they, what they need isn't what they always want. Right. You know this, they want sales, which, you know, it's a, it's an understandable, you know, a preoccupation at that stage. I mean, for me, if I'm starting a business right now, you know, it's that first 3 or 4 years of work that I need to get as much business as I possibly can, because that's what's going to first keep the lights on. But it's also the validation. I mean, the paying customer is someone who's saying I'm doing something right because people are willing to pay for it. And then it gives me the opportunity to prove my thesis on them and deliver values that I can make it better. And you need as much of that as possible, as soon as possible for a lot of reasons that sales becomes the main proclamation. But you and I both know without the infrastructure and foundation, you're sort of building it on top of something that's going to collapse. It's a really weird dynamic. So you need to have someone who sees that, right? And they're willing to sort of forego the short term for the long term at an early stage. So you need to find the right client who sees that and understands that. And those aren't always easy to find. How do you manage that situation?

Yeah. I mean, part of that is sometimes I'm right. Sometimes I'm wrong. Sometimes, you know, the founder tricks me. Um, you know, I, I get sold a, you know, bought whatever the same. Yeah.

Yeah.

And it often depends. And that's about like anything, me doing discovery and seeing if that CEO is a fit for me. You know, what are your goals? What are your objectives? What do you think success looks like for me based on the need? You called me. So what are you looking for? It also depends to a large degree. You know, I've worked with bootstrapped companies where it's very different obviously, than, you know, a company that's got, you know, $30 million in VC funding and pre-seed, and they've got investors telling them, doesn't matter what Neil or anyone else fucking says, you gotta, you know, very, very different. So every client has a different approach there. But it is at the end of the day about fit, right? It is about, does the CEO and myself when we're interviewing each other at the beginning. Does this make sense? Do they get it? If they say things to me like, yeah, Neil, I know, I know you're saying we should build, you know, build this out properly. But, you know, that's great. And you can do that. But I need X within 30 days. Can you do that? And I'm like, maybe, but I'm not going to sign on for that because I don't know what I don't know. And you don't have any— your whole company could be Freaking massive.

There's a lot of reasons why you're not getting it done in 30 days. And now you're going to make that my problem. And I don't want that. I want to fix that problem. There's a whole different—

I have a great, a short little story. Warren Zenna, I had a client recently who, great company doing really well. And I believe deeply that part of the issue is their compensation plan. Right? In that the way they're rewarding or not rewarding salespeople. Makes a huge difference in the actions it drives. And most of us get that.

100%.

You know, this particular person didn't necessarily agree with me. And so, you know, if I believe X and they believe Y, it's their company. So we're doing what they say, right? You know, but that, in my opinion, severely hampers the success they're going to have anytime in the near future.

Right. So it's interesting that what you just said kind of brings me to it. The major point, which is this one, which is so if I'm at a company as a full-time chief revenue officer and my job, let's agree on, let's say the purpose of this conversation, what a CRO is. And I have a strong opinion about that, which is that they run the whole like go-to-market. Their job is to oversee everything, you know, and, you know, build an engine where all those pieces are working together. Compensation and revenue. I mean, incentives are a part of that job. I should have a say in that. Like, it's not just we disagree. It's like, I can't be a CRO without having control for that. So I need you to hand that over to me. And I think that's where, if in fact I'm taking that job full-time, maybe not always, but I'm far more likely to have that under my purview because of my full-time position than not. So that's where these little weird compromises come in. And you know, you're right. You do have to sort of dance these things a bit and point out. But to me, Yeah.

To me, those are, I mean, without a doubt, there's a correlation. I agree with what you're saying. There's a correlation on it's more likely that you will have full, full control and ownership as a full-time than a fractional. There's no doubt about that. But I actually, my experience for me is it's client/founder specific. Yeah. I have a lot of clients I've worked with where I am the CRO. I have full control. They listen to me. They take my advice. That's smart. And then others, and others where it is definitely less so.

I, I get it.

For sure.

Yeah. Your ICP is the person who does, and I, I know you're looking for that person. Of course.

Of course.

And, as we are as well. I mean, you know, we, we see the problem we see. It's crazy. Is, we're dealing with companies that, you know, 50, 70, 80, 90 million revenues, you know, mature organizations. You know, they have product market fit pretty much at this point, but for making that much money, there's, something that's working obviously.

Hopefully. Hopefully. Yeah.

I know. It's, it's, I mean, maybe now there's a lot of, you know, there's a lot of like weird, like fake businesses, but I'm talking about real revenue, like real revenue with, with, with margin in it and stuff like that. Right. And they hire a chief revenue officer and they talk about all these constraints. We're, we're, we manage these things for them. We're like, why would you put that constraint on this person for? Like, what, like, what, walk me through. What's that? We know the answer usually. What's underneath it? Like, does it make sense to you? So, you know, if I were to bring this person on, given the gravity of the remit that they have for your business and the number you're going to tie to them, like if this person's successful, you're tying like $10 million more, $15 million more bucks on this person's back. And then you're going to say, we don't want you doing this.

Do you, Warren, do you find that that always comes down to a trust issue?

No, no, no, no. And I say the word no because, you know, trust is a strange word in that you could use that word in this instance, like, I don't trust this person to do that, or I don't trust the universe. It's a different thing. Okay. And I think they don't trust the universe. It's not the person.

It's like they don't trust it. No.

Generally speaking, they just sort of control is a way for them to manage the unknown. Right. It's just, I'm out of control and I don't know what I'm doing. So I'm just going to troll or control everything. Right. So, you know, I'm going to have to, and then the other part of it too is also some degree of, uh, weak, I'll say it, you know, some weak leadership. So, so for example, let's say we're at the point where we're going to bring a chief revenue officer on and we agree with the CRO collective that this person should run everything. We do, we do see the wisdom of that and we see how Not having done that has created all sorts of problems. And so we, we don't want to fix it. So they've arrived to the conclusion that this sort of centralized go-to-market control makes sense and they need someone that can come and they can do it. And then all of a sudden what happens is, you know, when they're, when the, when they're pressured up against actually having to make certain decisions around it, all of a sudden all these sacred cows come popping up that they didn't sort of articulate before. The first one, usually something like, Yeah, I understand what you said and we give it some thought, but we really want to keep, you know, Bob on marketing. I think it's better if he runs it, you know, it's like, well, what? Well, you know, he's been around for a long time. He's a really good guy.

I'm like, okay.

I mean, I understand he probably is. He's probably good at a ball game, but I mean, what's best for the business? What makes the most sense based on what we're talking about right now? What are we trying to solve for? Are we trying to solve for like relationships that you have, which I'm not saying are bad, but just let's talk about like what's really going on, right? And, you know, we do the math and they're like, yeah, you know, the calculus does make sense. It would make more sense for this new guy, Steve, to run it. But, you know, we just sort of feel like I just really don't want to piss this guy off or rock the ship or something like that, that it's meaningless in its comparison to what we're trying to do. But it ends up winning a lot of times. And again, much, much like the person who's taking the job, the owner says, we'll work it out. We'll figure it out. They'll work together, something like that, you know? And we're saying like, you know, it's just usually doesn't. Like, I'm sorry, but it doesn't, right?

Too many, I see that all the time where too many people put person names, names in the boxes long before they should.

Yep.

It's what's the role?

Yes.

Yeah. And then that gets in the way and clouds up the right thing for the business.

Totally. I don't want to be sort of like callous here. I know what it's like when you have people in your organization and you've, like, they've helped you throughout the whole thing and your company's maturing and you want to figure out a way to keep them because I totally understand. Believe me, I'm very empathetic to that reality. It's not an easy thing. I'm just simply saying that here's the way we play it out, right? So in the face of that reality, which is very compelling and you could sell it to me. I could say, you know, I get it. This person's been working here for 10 years. It makes sense to me. However, do the math. It's probably going to end up this way anyway. So what's more important to you? And they might say loyalty is more important. And you know what? I respect that. But, you know, you have to kind of like think about you're rolling the dice because what we see is that there are some things, some principles that just are like gravity, like they just work that way and they don't work the other way. And you just can't really do much about it.

The thing that always gets me on that, and I love, I love this topic, like is I respect too if a CEO or founder wants to be loyal to someone who's been with— I love it. I wouldn't love that.

It's a beautiful quality. No question.

But don't be scared of an honest conversation.

Yeah.

Go to that person who you want to be so loyal to that you must have known for 20 years if this is the case and say, I love you and I want you to be with me for a long time, but I need to be honest about what's going on in our business. Let's find something that works for both of us.

Exactly. Let's figure out some way to keep figure it out.

And if you want to give them a big bonus or, I mean, figure something, but don't affect your long-term business over it. Like figure out a solution.

People will sacrifice this for that stuff. And the other thing too, there's another dynamic too. Then there's the other less human side of it, which is more pernicious. And that is funding, right? So if I'm running a business and I'm at $70, $80 million business, it's likely that I've got a couple of rounds. That came in through some PE firm or VC firm. And they have an incredible amount of influence over everything now. And they don't care about anybody, right? They're for them, we're just a business that has a number and a goal and a projection. And we represent a cap table for them. And that's all they want. Right. And it's kind of chilly, but that's the way it is. So they look at it and they're like, look, you know, like we need you to just bring this person on as easy as possible. Frankly, right now, frankly, we just need We need the acquisition numbers to go up because that's really what's going to make a difference for us and the way we're managing the portfolio right now. That's really what we really want you to have this person do anyway. So I know you have these ambitions for this person to have all this power and stuff, but the truth is I'm really more worried about like fourth quarter than I am about your freaking foundation, you know? And so just get them to do that. And so they're pressured by those people and it affects their judgment and they come and say, look, unfortunately, You know, the board just frankly doesn't see it this way and I couldn't sell them on it. And so, you know, what ends up happening is there are a lot of, like, those are not necessarily political, but they're more sort of like the machinery of a business is sort of cold in a way and has very, in many cases, very short-term goals that have very little to do with customers at all. And so we see this happen when the CRO takes the job, you know, they're entering into a system. That they didn't build, but they're being told to own. And it's sort of like, okay, how is that system? Let's analyze it before you take the job. And how much control are you going to be able to have in reconstructing it in a way that's going to accommodate your job? Because if you don't, you're going to be stuck with a system that obviously isn't working or they wouldn't have brought you on in the first place. Now they're thinking without giving you the authority, you can't do anything about changing it. So what do you think is going to happen? So it's sort of like a really weird type of thing we're trying to help solve.

And that, to your point, goes back to the full circle of, did you punch yourself in the face or did you get all the information before you signed up? Is it in your control to be successful or not?

They're not. And then what do you do about that? Because then on the other side of the equation, you know, we have our clients who don't always have a year to hang out and get a new job.

Yeah. Yeah.

They have like 3 months or 2 or 4 months to get a new job. And I understand. They got little kids and they got all the stuff that you and I both know exactly what that's like. That's like, that's the scariest thing in the world.

So they make, they make choices.

Noble, noble choices to walk into a situation that is likely dead from the moment they take the job because they had to feed their family. And I love these people for that. But I also know that, you know, if there's some way that they could have bought themselves 3 or 4 more months, we could, no question. Put them into a job. Not, we're not recruiters, we're consultants in CRO readiness, getting them into a situation where they have a lot more of that control and that job will feed their kids a lot longer. And that's what we're trying to do. So we look at jobs in the earlier stage, like what you're doing, you're, you're, you're, you're solving a really important problem. When does, in your view, your job end? When is it like, usually, you know what, you don't need me anymore. You need to get someone full-time. How do you talk about that?

Yeah, I love that. And I use that kind of storytelling or analogy. You know, my job is to put myself out of a job in a perfect world. Yeah. Yeah. You know, and I say that to the CEO. I say, you know, based on where you're at and what your numbers look like and so on, you know, I think it does make sense to hire me because there's some things we need to build or fix or improve, et cetera, whatever the case may be. But if I'm still here in 6 months, it means We both, we failed. Yeah. You know, and obviously the goal is to get it, get the business to a point where hiring a full-time expensive CRO makes good sense and pays for itself many times over.

Sure.

Right. That's the goal. You know, and I've done that before where I've actually helped and I love those engagements where I get the honor of saying, okay, we're at a point. And the CEO says, let's hire a CR full-time. And I get to help recruit and interview that person, which is really fun and exciting too.

Sure.

And better for everyone because now I can tell the whole story to this potential candidate of everything we've done very closely. And hey, Sally, here you go. It's ready for you. I mean, you're going to do what you want with this, but I believe it's in a really good shape for you to take over and now go and optimize. As opposed, as opposed to spend 6 months trying to figure shit out and building it.

Exactly. Yeah. No, that's a good thing. It's a good thing. Thank you so much again for listening to the Sierra Spotlight podcast. This podcast is an important plank in the Sierra Collective communication strategy. And we're really thrilled to have such great guests on here. So 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. Couple 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. Uh, 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 a 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 newly hired CROs. Take advantage of it. It's been great. And you'll see some more information about it on the website.

Thanks. Yeah.

How do you deal with like, you know, we find happening is So I had a really interesting situation recently where we brought in somebody to a company. They had already had a CRO beforehand, you know, and it didn't work out, but, but the CRO that was beforehand for reasons that didn't matter, did end up actually building a pretty decent foundation for this company. Like they did do some work that was solid. It was good. And so, you know, we brought in this new person. You know, they, we worked with them to find somebody. It wasn't, it wasn't the traditional sort of like job placement thing. It was more like a consultant anyway. And, you know, there's this need to sort of like say, well, I think it's great, you know, that this person did all this work, but now I want to do that work. I want to look at it and I want to see how maybe I see something differently because I'm pretty smart and I have a methodology. If I don't put my methodology here, then. You know, there's this sort of feeling like, I don't want, you know, you know, it's like you buy a house that's been decorated, you want to decorate it yourself and you rip everything out, you put in your own stuff.

Yeah.

You know, how do you maintain the integrity of the work you do when someone comes in and they feel like they want to start over and redo it again? It happens all the time.

Yeah, I guess, I mean, most times I'm not there to know, frankly.

No. Yeah.

But I mean, I think that's two things. One, what you've just described, I think, is the difference between good CROs and shit CROs.

Yeah.

Right. Ones who are not control freaks or think they need to fix things that don't need fixing. They come in and they hopefully say, hypothetically, wow, I'm so lucky to come into this situation. Look at it all. I may have some slight adjustments as I learn more. But it's ready to go for the most part. Here's where I'm going to make a difference in terms of team management and coaching and executing everything versus having to redo things that don't need redoing just to put my own frickin' name on it.

100%.

And I think that comes in, in the interview process, right? I mean, it's like finding the right candidates who understand and ask the right questions and get excited when I tell them, here's what we've done for you. Here's what's in place. If they get excited, say, holy cow, this sounds like, you know, I can't wait to just execute what you've built versus other things like, well, I'm going to have to take a look at it. And, you know, I mean, it's like anything, you know, it's making sure you get the right person for that stage. If you're hiring a builder, that's different than where we are now as a stage. I was hired in most cases as the builder of the go-to-market. Process system and team. We don't need that now. Now we're ready to execute much, much more in a consistent manner and drive the numbers so that, like anything, your hiring should be stage specific to what you need at that time.

Yep. It's almost like you need to have a solid diagnostic that it's, it's dumb enough to not know the difference between who built it or not. It's just measuring things. So if it matches up, it doesn't matter who did it, right? So I want to switch gears a bit before we sign off here. How is AI affecting your job? Like, in what way are you using it? In what way are you seeing its impact on the people that you're helping? And how is it changing what you do?

Yeah, I love— man, I mean, we could talk forever on this. Like most things, and most of my answers is very specific to who I'm working with.

Of course.

If I'm working with, you know, B2B SaaS tech companies, What we're doing with AI is very different than— I get the luxury of sometimes working with what we might call more traditional, older school industries. I worked with a workers' compensation company a year or so ago, very, very different approach to technology.

Yep.

You know, like doing basic, basic things in technology, incredible, lucrative, amazing business, just wasn't a high-tech business, you know, so doing the most basic of things with AI was like, holy, you're a hero. Like, it's amazing the work you can do. Most of my clients are pretty tech savvy and, you know, becoming more and more AI native or AI savvy as well. So we're doing lots of different things, just like any CRO hopefully is and should be doing, you know, from trying to build out different agents to help optimize and drive efficiency, trying to get rid of repetitive work that someone's doing that theoretically shouldn't need to be done anymore by a human, trying to find opportunities for humans to use their actual human superpowers more often. Everything from admin work and CRM crap that of course should never have to be entered anymore these days by anyone. And then personally, I'm doing a lot with my own business in terms of building out my content and playbooks and things. Right now, I'm building out, and, you know, everyone's doing this, so it's not something special, but taking all, you know, I've got 50 different decks and presentations of playbooks and content, bringing it all together into a master lovable website domain that will have multi-client tenants in it. So now instead of 97 documents, as I build out with a client, I could just give them access to everything in one spot, in one place, give them role permissions and so on. So I'm loving the learning that I'm doing at my old age, but amazingly fun and really, you know, much more consistent, easier to manage. And maybe even for myself from a selfish business perspective, maybe even be able to turn that into a revenue stream. So that after I leave a client, if they want me to maintain that, you know, Client X playbook system, you know, there's a little bit of recurring revenue there that they can have that as opposed to having 97 documents on their SharePoint. That's a fricking mess. Yeah. So there's different ways that it's a win-win for everybody.

Yeah.

Yeah.

It's pretty exciting, right? It's kind of crazy what's possible right now. What we're doing similar things. It's like every day we're like, wow, we can do this, we can do that. Holy shit.

Yeah, it's amazing.

We're also seeing that the CRO role is changing because of this. It's a different job now, you know, it's not the same. And I don't know, frankly, if the sort of traditional sales-focused CRO really is a relevant beast anymore. I think they really need like RevOps people who know how to build stuff, but have leadership confidence. It's a very unique person. It's like someone who's sort of operational, but also knows how to like deal with the board and like politics. It's really fascinating. Profile. So we're seeing a lot more of that happen now to a shift in the way people are being viewed for this, this position right now.

Yeah, I don't disagree. I mean, you know, a great CRO, I think we get caught up in the noise a lot. I feel like a great CRO was always to a large degree these things. They always understood how to help companies become more data-driven and they understand the tech stack and what tools they need to be efficient and effective. And of course they need sales skills and be able to coach and relationship building superpowers. I don't see that as any different. And, and sure, a great RevOps person can become a CRO. There's lots of them and, and there will be lots more. There's no doubt about it. Ryan Milligan from QuotaPath just went from head of RevOps or VP of RevOps to CRO. He's amazing. And I think there'll be more of those. But I don't think, I don't think that, you know, to me, it still comes down to the human element. I still think irrelevant of what role they came from, CMO, Chief Revenue Officer, or sorry, RevOps leader, sales leader, VP of sales. I think we all get caught up in this, like it has to be one or the other. Two years ago, everyone was saying, well, CMOs are the future of the CRO role. It changes on trends.

Like, that's true.

I think it's all bullshit. I think it's anybody in any function can become the CRO if they have the right skill sets and ambition to do so. Agreed. But yes, without a doubt, today in 2026, obviously people who are AI native understand how to use technology to be more effective and more efficient. Clearly that is a superpower that is now needed more than ever before to be a great CRO. There's no doubt about it, but I don't think that means the other stuff is less important.

That's fair. I think it just adds more complexity to the role, not subtracts the other stuff. It just makes it more sort of diversely kind of complex, if you will.

Yeah.

So this is great. I mean, I love talking with you. I really appreciate you being here very much. So No, what's the way people can get ahold of you? What will have people, where people find you, who you want to talk to?

Yeah. Um, I, I love talking to everyone and anyone just like you do. I have too, too many times I say yes and not enough nos for, I don't have the time for it, but I love it and I enjoy it. Um, so if anyone wants to reach out, they, you know, I'm a LinkedIn guy like you, Warren. So LinkedIn DMs are probably the easiest way to remember to. If you wanted to get a hold of me and we could chat there and see if it's worth the conversation. But most of all, Warren, I appreciate you. I've been following you and hearing great things about you for a long time. So it's an honor to chat and be on the podcast and shout out to our mutual friend Jessica, who told me, definitely go on Warren's podcast. He's awesome. So yeah, no, thank you for having me, Warren. It's been a pleasure.

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 Join us next time.