The CRO Spotlight Podcast

Warren Zenna: 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 [00:01:00] 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," you know, so I was really glad because I've heard of Neil Weitzman before many times. We sort of are LinkedIn buddies in a way. We never actually met. So Neil, I'm really 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 all of your content so welcome and thanks for being here.
Neil Weitzman: Thank you. I am honored to be here. It is great to meet you in person on the Zoom call here, Riverside. But thank you for having me. It's a pleasure and I can't wait to argue and debate with you.
Warren Zenna: Tell me a bit more, I know a lot about you already, but tell my listeners who are mostly chief revenue officers and aspiring chief revenue officers and go-to-market leaders. So you were at [00:02:00] Nielsen for like an entire generation, like you were almost there, like five 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 long corporate gig sort of set you up for where—
Neil Weitzman: Yeah. And I love the way you say for a generation is a polite way of saying Jesus, hell, you're old. 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 and 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, right? Some of the industries I came from don't [00:03:00] use titles like that, but that doesn't mean you're not doing the same job.
Warren Zenna: A hundred percent.
Neil Weitzman: Yeah. So I've been a leader in sales, marketing, you know, rev ops, et cetera, 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 weitzmanGTM, where I do GTM Advisory. 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.
Warren Zenna: Great. I love it. So you go to the market or what? Get the fuck out. Is that basically what it is kind of right.
Neil Weitzman: I think you're referring to my aptly named newsletter, GTM or GTFO. Yes.
Warren Zenna: Right. No. 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 where that drove, obviously some provocation must have had you wanna make that claim.
Neil Weitzman: I think I, I mean, to be fair, I was having a—
Warren Zenna: To be provocative.
Neil Weitzman: Labeling and marketing, but without a doubt, I do believe, as you know, many of us have talked about over the last couple 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 a good GTM looks like. And we can talk about that. But, 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, then you know the world's your oyster, right? If you could just be better than 99% [00:05:00] of the crap out there that we see, you're probably going to be okay. Even though GTM is incredibly hard.
Warren Zenna: 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. 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 you want to refer to it, is so messed up. Like why is it that regardless of the amount of information 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?
Neil Weitzman: 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'm just making up a number here, the top 200 large B2B SaaS AI companies that were, you know, hundreds of millions, a billion, 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, and it looks like that on LinkedIn. Many of us see. So I feel like a lot of it is an 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 [00:07:00] doing and don't. Go to someone they trust and you know, 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.
Warren Zenna: So you think it's more sort of like you said it, like an echo chamber. 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. I sort of look at it like businesses are like humans in 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 [00:08:00] 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 all ultimately find ourselves saying, "Wow, you know, my parents were really right." You know, and they're saying like, "Well, you know, if you figured 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 a lot of our clients. I'm like, "You know, you probably know 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 [00:09:00] that you find you enter the market? What's your client profile? What size are they emotionally?
Neil Weitzman: Yeah. And it's a great topic. Most of my clients would range from 2 million to 25 million ARR types of size. So let's call that generally speaking, pretty early stage.
Warren Zenna: They're teenagers, right? They're adolescents. They're post-adolescent. The CEO is still the person that probably founded the company, right?
Neil Weitzman: In most cases. Yep.
Warren Zenna: Most cases, right? So like you said, they're like in that sort of 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 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 learn the lesson now in a way, right.
Neil Weitzman: Yeah. My job as a, let's just use the word fractional CRO for a moment, [00:10:00] 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—
Warren Zenna: Sure. I understand. Sure.
Neil Weitzman: But you know, quite often I do a decent job and I am right. And they don't—
Warren Zenna: 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—
Neil Weitzman: No, it's okay.
Warren Zenna: My clients tend to be more post 25, 30 million for various reasons, which [00:11:00] might in fact actually have us agree on a lot more because of that. But 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? 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, so I don't wanna be here anymore?" Or was it "I had enough of this?" Like, what was it that happened?
Neil Weitzman: Yeah. Well, without getting too personal, because—
Warren Zenna: I understand. I'm just curious because you were there for a brief time and that was—
Neil Weitzman: Yeah. I was not there.
Warren Zenna: You know?
Neil Weitzman: Yeah, I was not there for a long time. We parted ways, me and that company, literally March 2020, which I believe was COVID, one of the first real months where everyone was like, "Go home, no one's—"
Warren Zenna: This is happening. Yeah. Yeah.
Neil Weitzman: Yeah. So, we parted ways for various reasons and it had some bearing on what was going on in the world. But what triggered for me, irrelevant of [00:12:00] that situation—
Warren Zenna: Sure.
Neil Weitzman: 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 gotta decide for themself 100%. But 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 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 out. And I had 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. [00:13:00] 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.
Warren Zenna: That's great. I love it. I mean, similar, right? I think that there is a, what we deal with a lot of chief revenue officers who go through the trials and tribulations of these jobs and you know, the emotional damage it does to people. 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 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 will [00:14:00] say this sort of thing is, you know, "Having been punched in the face too many times, I finally decided I didn't wanna." 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, that he punched himself in the face. And here's what I mean. Is that similar 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 that aren't going to work about it, but they take the job anyway and they sort of hope it'll work out or 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 [00:15:00] job. And so we do a lot of this work with people because again, in the role that we're helping people in that post 25, 30 million range, 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, 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 again, I have no issue with that. I think it's a completely honorable thing. 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 gotta 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 someone who comes along at an earlier stage, what you [00:16:00] do given that context is actually a hundred percent appropriate because that's exactly what they need at that stage, is somebody like you. They shouldn't hire—
Neil Weitzman: Very, stage specific.
Warren Zenna: A hundred percent. A hundred percent. 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, "Alright, bring us some maturity. You know, get us where—"
Neil Weitzman: Not nearly enough money for the record, should be way more.
Warren Zenna: So walk me through, you must have a methodology, an approach, that kind of thing. So when you get an engagement, what sort of way do you view the world, their world, so that you can have an impact on it?
Neil Weitzman: Yeah. And I want to answer that. I also just want to reflect on something you said that, you know, even in my latest full-time CRO job, I made that mistake, I punched myself in the face.
Warren Zenna: Everyone does.
Neil Weitzman: I could reflect back and say, "How did this end up how it [00:17:00] 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've learned so much more that probably would've said, "This isn't the right job for you, Neil."
Warren Zenna: 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.
Neil Weitzman: Yeah, so I just wanted to reflect on that because you're totally right. You're totally right. In terms of 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. I do believe, of course, there's a lot of the same [00:18:00] elements that you have to cover off. Without a doubt, we need to make sure, for example, you know, the cliches most, like where do you start? Well, what's your ICP? What are we focused on? 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 does it come into the system? So all of these things are 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?" We go through all these different questions and [00:19:00] it helps me understand if there are improvements that I can make if I were to join the team on a fractional basis. 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 [00:20:00] 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've been a CRO many times, so 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 to see where we should double down versus optimize and so on.
Warren Zenna: Hey everyone. I want to thank you again for listening. 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 two and a half years ago, we started the CRO roundtables. Predicated on the idea that, well, two premises. One is that 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, [00:21:00] 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. Essentially it's a three and a half, four hour discussion 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 y'all know that we have a number of the roundtables coming up over the next year, over the next like 2026. And 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 LinkedIn. But early on your calendar. And then following that, we're probably [00:22:00] 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 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 wanted to talk about as a Chief Revenue Officer and collaborate with great people. So, thank you and thanks for supporting the show and look forward to seeing you at the events.
Got it. So, you know, I really, I think you said something I love to dig into [00:23:00] because I agree with you. And that is, 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 our or your, my particular expertise, area of expertise, can bring to bear on your organization, right? It's just a framework through which we can bring our expertise to bear on your business, whatever that might be. So how would you define yours? Is it more like you're data driven? Are you more process driven? Are you looking at things more holistically? Like if you were to sort of try to articulate your philosophy, what, how would you say that Weitzman philosophy sounds like differently from somebody else's?
Neil Weitzman: Yeah. Oh, wow. You're really [00:24:00] 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 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—
Warren Zenna: It's okay. No.
Neil Weitzman: Cocky, or let me put it this way, the reason I win the deals I win is because of a very clear ability, just like I said on my website, to execute and get shit done. I feel that my attitude and my approach to working closely with [00:25:00] CEOs especially, and specifically at the early stages where founders are about executing and getting shit done as quickly as possible.
Warren Zenna: No question.
Neil Weitzman: 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 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, that's what it is, 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."
Warren Zenna: Gotcha. So, [00:26:00] given that, again, that goes to the earlier point that I was making in our original LinkedIn conversation: 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's where some of the stuff I see I have a lot of colleagues who are in business you're in.
Neil Weitzman: Sure.
Warren Zenna: I'm not anymore. And if I really were to do the job I'd need to do more and I can't because they're not paying me enough so the scalability is there.
Neil Weitzman: Yeah, it is. That's the hardest part for sure, Warren, and especially for me, I get really passionate about my founders and clients I work with, so it's very hard for me to like to turn it off and not give them more time than the time we've agreed. 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. 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 [00:27:00] 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 not time-based so much, but there is a sense of that. So generally my packages are kind of like approximately a day a week, or approximately two days a week, which means of course, you know, three-ish clients is like the maximum I should kind of be taking on without going absolutely crazy. And that's the way I try to think about it. You know, I mean, even if they're a day a week-ish, three clients a day a week, some people will say, "Well, you've got two more days." Well, the reality is when you're jumping around client to client, it's much harder. And like any good salesperson, I need to leave time for building my own brand and my own business development.
Warren Zenna: Yeah. Yes sir. You do. I did what you did for a while, quite a while, so I understand exactly what you're saying. And I went through this [00:28:00] problem because I too, I'm like you, I tend to say yes, and I want to help people and yeah, I get into it, you know, it sort of turns the spigot off. In fact, even here, I have people I work with now in my company, like, "Warren, you're talking to too many people. Be a little bit unavailable. It's totally fine, you know."
Neil Weitzman: Right.
Warren Zenna: But, you know, I try to like talking to people. Someone asks me a question, I want to answer the question, you know. I feel like a little boy a lot of times in 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 the clients know that, aside from the obvious, which is "I'm making more money." Just the minutia, like the day-to-day ways, which clients know. Aside from "I'm getting attention from Neil," do I know that making [00:29:00] metrics that you know.
Neil Weitzman: Yeah, I mean every client, I mean, there's some similarities, but they're all a little different too. Right. I 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 other 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 [00:30:00] human. And literally within two weeks I was getting messages, "Oh my god. One of the biggest clients and prospects responded to me after three months of not responding." And so aside from all the data, you know, just that type of evidence. And 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 a pipeline if you can't get responses and actually talk to people. So, you know, a very simple example there. The one thing I'd point out, Warren, is you know, I said in a very flip 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 are a couple nuances, of course. And one of the nuances is it is hard to [00:31:00] hold me accountable to a metric when I'm not there full time. 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 because I'm not there all the time, right? I'm not going to be able to be involved and jump onto client calls like a real 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 are 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 [00:32:00] role. Now, it doesn't mean I can't affect change and make a difference, but there are two different things.
Warren Zenna: 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 to share the 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 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 bi-monthly group of six seasoned chief revenue officers who are looking for a chief revenue officer board of directors, so to speak, so 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 six months to a year. So if you're [00:33:00] 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 Master's Council, which we have a number of them being put together right now, just go to my LinkedIn and DM me "masters" or "Master's 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 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 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, those [00:34:00] are precious dollars they're giving to you, right? I mean, they're carving up that budget and they're giving me a nice amount of money for things like, "This has gotta do something for me." 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 understand. 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."
Neil Weitzman: Yeah, there's a key difference though, that I think is to, let's 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 [00:35:00] because they need a foundational GTM process, system, tech stack, handoffs team, everything built out. So it's as much about a building initiative as it is an optimizing initiative.
Warren Zenna: Look, I agree 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. And you know this, they want sales, which, you know, it's an understandable preoccupation at that stage. I mean, for me, if I'm starting a business right now, it's that first three or four 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 value so that I can make it better. You need as much of that as possible as soon as possible. For a lot of reasons that sales becomes the main [00:36:00] preparation. 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 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?
Neil Weitzman: Yeah, I mean, part of that is sometimes I'm right, sometimes I'm wrong. Sometimes, you know, the founder tricks me. You know, I get sold, you know, whatever the saying is. Yeah. And it often depends. And that's about like anything, me doing discovery and seeing if that is a fit for me. "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 is [00:37:00] 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 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, "Neil, I know you're saying we should 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 your whole company could be a freaking mess. I have no idea."
Warren Zenna: A hundred reasons why you're not getting it done in 30 days, and now you make that my problem. [00:38:00]
Neil Weitzman: Yeah. For a great, short little story, Warren. I had a client recently who, great company doing really well, and I deeply believe that part of the issue is their compensation plan, right? In that the way they're rewarding or not rewarding salespeople—
Warren Zenna: Mm-hmm.
Neil Weitzman: Makes a huge difference in the actions it drives, and most of us get that.
Warren Zenna: Hundred percent.
Neil Weitzman: 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, you know. But that, in my opinion, severely hampers the success they're going to have anytime in the near future.
Warren Zenna: Right. So it's interesting that what you just said kind of brings me to 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 [00:39:00] CRO is and opinion that job is building an engine where pieces, compensation and revenue. I mean, incentives are a part of that job. I should have said 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—
Neil Weitzman: But 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 control and ownership as a full-time than a fractional. There's no doubt about that. But actually, my experience for me is [00:40:00] it's client slash founder specific. 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. And then others, where it is definitely less so.
Warren Zenna: I get it. Your ICP is the person who does, and I know you're looking for that person. Of course. And, as we are as well. I mean, you know, we see the problem. What 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—
Neil Weitzman: Hopefully. Hopefully, yeah.
Warren Zenna: It's, I mean, maybe now there's a lot of, you know, there's a lot of weird, like fake businesses, but I'm talking about real revenue, like real revenue with margin in it and stuff like that, right? And they hire a chief revenue officer and they talk about all these constraints. Like we're managing these things for them. We're like, "Why would you put that constraint on this person for like, what? Like, walk me through." 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, 'Eh, we don't want you doing this.'"
Neil Weitzman: Do you, Warren, do you find that that always comes down to a trust issue?
Warren Zenna: No.
Neil Weitzman: No.
Warren Zenna: 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 the universe. No. They, generally speaking, they just sort of control is a way for them to [00:42:00] 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, we, 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. So we 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 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 wanna keep, you know, Bob on marketing. We think it's better if he [00:43:00] 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. Just let's talk about 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 wanna 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 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 just usually doesn't, like, I'm sorry, but it doesn't." Right. And—
Neil Weitzman: See that all the time, Warren, too many people put [00:44:00] names in the boxes long before they should.
Warren Zenna: Yeah. They promote people too soon. Yes.
Neil Weitzman: And then that gets in the way and clouds up the right thing for the business.
Warren Zenna: Totally. I don't wanna be sort of callous here. I know what it's like when you have people in your organization and 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 can say, "You know, I get it. This person's been working with you 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 to me." And you know what, I respect that. But you know, you have to kind of think about rolling the dice because what we see [00:45:00] 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 otherwise.
Neil Weitzman: The thing that always gets me on, and I love this topic, is that I respect it too. If a CEO or a founder wants to be loyal to someone who's been with them, I love that.
Warren Zenna: Who wouldn't love that? It's a beautiful quality, no question.
Neil Weitzman: But don't be scared of an honest conversation. 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, 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—"
Warren Zenna: Exactly. Let's figure out some way to—
Neil Weitzman: Let's figure it out. And if you want to give them a big bonus or, I mean, figure—
Warren Zenna: Something to do.
Neil Weitzman: But don't affect your long-term business over it. Like figure out a—
Warren Zenna: People will sacrifice this for that stuff. And the other thing too, there's another dynamic too. Then there's [00:46:00] 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, it's likely that I've got a couple of rounds that came in through some PE firm or a VC firm, and they have an incredible amount of influence over everything now. And they don't care about anybody, right? 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, we need you to just bring this person on as easy as possible. Frankly right now, frankly, we just 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. And that's really what we really want you to have this person do anyway. So I know you have these ambitions with this person to have all this power and stuff, but the truth is I'm really more worried about the fourth quarter than I am about your freaking foundation, you know?" And [00:47:00] 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 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. Another way of thinking without giving you 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, tough [00:48:00] thing we're trying to help solve.
Neil Weitzman: 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?
Warren Zenna: They're not. And then what do you do about that? Because then on the other side of the equation Neil, we have our clients who don't always have a year to hang out and get a new job. They have like three months or two or four 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 the scariest thing in the world.
Neil Weitzman: They make choices.
Warren Zenna: We make choices, which are noble 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 three or four more months, we could no question, put them into a job. No, we're not recruiters, we consult and do CRO readiness, [00:49:00] 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 solving a really important problem. When does, in your view, your job end? When is it like, "You know what, you don't need me anymore. You need to get someone full time." And how do you talk about that?
Neil Weitzman: Yeah, I love that. And I use that kind of storytelling or analogy. My job is to put myself out of a job in a perfect world. 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, 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 six months, it means we both failed." You know, and obviously the goal is to get the business to a point where hiring a full-time, expensive [00:50:00] CRO makes good sense and pays for itself many times over. 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 full-time." And I get to help recruit and interview that person, which is really fun and exciting too, 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 to spending six months trying to figure shit out and building it.
Warren Zenna: Yeah. No, that's a good thing. It's a good thing.
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 [00:51:00] 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. A couple things to note. 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 five 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 more 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 rev ops leader. And they either want to move into the C-suite or they're CROs that want to [00:52:00] 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.
Warren Zenna: And how do you deal with, you know, what 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 the CRO that was beforehand for reasons it didn't matter, did end up actually building a pretty decent foundation for this company. Like they did some work that was solid. It was good. And so, you know, we brought in this new person, you know, we worked with them to find somebody. And the whole thing, it wasn't a traditional sort of job placement thing. It was more like a consultant anyway. [00:53:00] You know, there's this need to sort of 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 wanna look at it and I wanna see how, maybe I'll 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, you know, it's like you buy a house that's been decorated, you wanna decorate it yourself. You rip everything out, you put in your own stuff. How do you maintain the integrity of the work you do when someone comes in and they feel like they wanna start over and redo it again? It happens all the time.
Neil Weitzman: Yeah, I guess, I mean, most times I'm not there to know.
Warren Zenna: There. No. Yeah.
Neil Weitzman: 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, right? Ones who are not [00:54:00] control freaks or think they need to fix things that don't need fixing. 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 freaking name on it." And I think that comes in during 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 and 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 [00:55:00] stage. If you're hiring a builder, that's different from 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.
Warren Zenna: Yep. It's almost like a need to have a solid diagnosis. That 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 matches up. It doesn't matter who did it. Right. So I wanna switch gears a bit before we sign off here. How has AI affected 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?
Neil Weitzman: Yeah, I love, man, I mean, we could talk forever on this. Like most things, and most of my answers are very specific to who I'm working with. If I'm working with B2B SaaS tech companies, what we're doing with AI is very different from how I get the luxury of sometimes working with what we might call more traditional older school industries. I worked with a compensation company a year or so ago, with a very, very dark approach to technology. You know, like doing basic, basic things in technology, incredible, lucrative, amazing business. It 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 [00:57:00] to be done anymore by a human, trying to find opportunities for the 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 [00:58:00] 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 freaking mess.
Warren Zenna: Yep. Yep.
Neil Weitzman: So there's different ways that it's a win-win for everybody.
Warren Zenna: Yeah. Yeah. It's pretty exciting, right? It's kind of crazy what's possible right now what we're, we're doing similar things. It's like every day we're like, "Wow, we can do this. We do that. Holy shit." And 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 [00:59:00] really need people who know how to build stuff. But have leadership competencies. He's a very unique person. It's like someone who's sort of operational but also knows how to deal with the board and fight politics. It's a 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 position right now.
Neil Weitzman: 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 sure, a great rev ops person can become a CRO. There's lots of them. And there will be lots more, there's no doubt about it. Ryan Milligan from Quota Path just went from [01:00:00] head of rev ops or VP of rev ops to CRO, he's amazing. And I think there'll be more of those, but 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, rev ops 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. I think it's all bullshit. I think it's anybody in any function can become the CRO if they have the right skillsets and ambition to do so.
Warren Zenna: Yep. Agreed.
Neil Weitzman: 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, [01:01:00] 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.
Warren Zenna: 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 a diverse kind of—So this is great talking.
Neil Weitzman: Yeah. I love talking to everyone and anyone just like you do. I have 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. So if anyone wants to reach out, you know, I'm a LinkedIn guy like you Warren, so LinkedIn DMs are probably the easiest way to remember too, 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 [01:02:00] 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.