Finding and Winning Your Next CMO Role

Drew: Hello, Renegade Marketers! If this is your first time listening, welcome. If you're a regular listener, welcome back.

In this episode, executive recruiter Erica Seidel joins one of our monthly Huddles for CMOs in transition to unpack what's really going on in the CMO market. She gets into what CEOs are actually hiring for, why some roles are tougher than they first appear, and how marketing leaders can read the context more clearly before stepping into the wrong situation. If you like what you hear, please subscribe to the podcast and leave a review. You'll be supporting our quest to be the number one B2B marketing podcast. All right, let's dive in.

Narrator: Welcome to Renegade Marketers Unite, possibly the best weekly podcast for CMOs and everyone else looking for innovative ways to transform their brand, drive demand, and just plain cut through, proving that B2B does not mean boring to business. Here's your host and Chief Marketing Renegade, Drew Neisser.

Drew: Hello, Huddlers. If you're here, you're thinking about your next CMO role, quietly preparing for it, or trying to future-proof the one you have. This is our third conversation with Erica Seidel, and there's a reason we keep bringing her back. Erica runs a highly respected boutique recruiting practice called The Collective Good. She is hyper-focused on CMOs, like we are at CMO Huddles, especially for B2B SaaS orgs, and they're often PE-backed. I don't want to hear any booing — probably for me. Her tagline is that she recruits the "make money" marketing leaders, not the "make it pretty" ones, and we'll get into that in a little bit. She works closely with CEOs, boards, and investors, and has a front-row seat to how CMO hiring really happens — not how it's described in job specs, but how decisions actually get made. It's funny. I got to review over the weekend our past two conversations, and she's helped us confront some hard truths: the fact that companies are often looking for an 11-out-of-10 on requirements, the fact that companies don't want to squint when they hire, the reality of CMO roles often being revenue rescue missions, and the emotional toll of modern CMO careers. Today, we're going to build on that and look ahead to what it will take to win a CMO role in 2026 — not just how to interview better, but how to choose the right situations, tell the right stories, and show up with confidence in a market that is more demanding and more ambiguous than ever. This is meant to be candid, practical, and hopefully a bit of a pep talk. So Erica, welcome back. How are you and where are you this fine day?

Erica: I am well, hi Drew. I'm at home in Cambridge. 

Drew: Cambridge, Mass?

Erica: Cambridge, Mass. Yes! Down the street from Harvard Square.

Drew: This is the first time I've ever worn a turtleneck on any CMO Huddles recording, because it's chilly here, and I imagine you're feeling the same.

Erica: I have a couple of layers, you know, just a few pairs of pants on and, yeah, yeah, 

Drew: But we're ready to rock. So, okay, we spoke early last year. I'm wondering if you're seeing any sense of fundamental change in how companies are evaluating CMOs. 

Erica: One thing I'm actually happy to see is that when I have asked CEOs in the last few searches I've done, "What kind of marketing leader do you want? Brand? Demand? Product marketing?" — you know, I do primarily B2B SaaS companies, right? — they are more likely now to say, "I don't really know. I don't really care. I want an orchestrator. I want a growth partner. I want somebody to up-level the function. The person could come from anywhere," which is a little bit different than what sometimes people say, which is like, "Oh, it's all about demand. It's all about demand." And I think that people are realizing — maybe it's all the badgering that, you know, the marketing organizations, you know, marketing people have done — that the way forward, especially in kind of AI where AI has joined the buying committee, is like tight cycles of brand and demand. So that's, that's very exciting. I saw this quote from John Miller: "Pipeline problems are positioning problems." And I think that we collectively — maybe we have made, you know, kind of headway in that brand versus demand conversation. I think in another area, maybe going from like AI-curious to AI for efficiency to AI for elevation — that's kind of like an evolution. I haven't yet dealt with, "Oh, we want you to use AI and ditch your whole team," right? I'm sure that could be out there, but, you know, I haven't yet come across that. There was this joke that was floating around, like, "Oh, you're not gonna get hired unless you've done something like, you know, five custom GPTs that you can show us." So I don't know. I think where everybody's still figuring out is like how to get at the AI question, the AI fluency and stuff. 

Drew: Let me stop you there for a second, because I have felt that the brand versus demand thing was a false dichotomy for a long time. And so I am — sort of — the last thing I would want to ask a CEO is, "Do you want brand?" Because I don't think they ever understood what the distinction was anyway. 

Erica: Yes, thank you. Yes. Yeah, you're right. 

Drew: So hopefully they're just saying, "I want somebody who can grow the company," and I get that. What I'm trying to figure out here is — because I increasingly hear from CMOs whose CEO or founder clearly doesn't understand there's a process here, that you just can't generate sales day one, and that there are things that have to happen. So I'm wondering, when you're talking to the CEOs, do they have any clue how marketing is working? And if not, what does the prospective CMO have to do to educate them on that and then get the job?

Erica: It depends, you know. I mean, some CEOs rather have done a stint in marketing, or they have learned from good people. Sometimes it's just a kind of "What Got You Here Won't Get You There" with, you know, hiring — like, we've had somebody good, and now we want somebody who can, kind of, navigate this tough market that we're in. It depends in terms of what you need to do. You need to show how you have increased revenue and how you've gotten a lot done on a tight budget. So I often get clients asking, "Well, what did they do? Oh, great. Well, what was the budget that got them there?" And just demonstrating that with the team. And I also think just educating as you go — like, I mean, you brought it up yourself, the whole brand versus demand conversation is maybe not that helpful and maybe a little bit oppositional. And I think the strongest CMOs are ones that will kind of, you know, be almost a little bit like, I don't know, like therapists internally — they just kind of bring people along with them, and they're not going to be like, "What's your view of marketing? Oh, my view of marketing is very different." I think the other thing here is just like, there's such an interest in experiments, and so talk about the experiments that you're running. I interviewed somebody for my podcast, Monica Ho — she's awesome, she's a CMO. I don't know if she's in this group, but she talked about how she was trying to get AI adoption on her team, and she kind of just gave them a lot of tools, and then that didn't really help. And then she said, "Okay, I'm just going to start taking away the tools that you're used to using, and you have to use AI." And so I just said — that's stuck in my head as a really good kind of way of dealing with the organizational change of AI, you know, that kind of use case.

Drew: I want to get into AI, but not yet — doing the fundamental thing here. So, this is a small point, but your last job: let's say you were in it for six to 12 months, and the company did not grow. But in your earlier job, you did have a growth story. And sometimes, let's face it, there are companies where the headwinds are so strong. I mean, right now, generally every SaaS company is facing a crisis. So the fact that you didn't grow the company may not be because you were a bad marketer. It may be that you weren't able to persuade the CEO and the product people that we need to change what we're doing, right? It's a go-to-market problem and not a marketing problem. But in those cases — which I see more often than I'd like — they weren't able to grow the business. Do they go back to the one use case that they did before, where they do have a growth story? I mean, how do you handle that specific one?

Erica: Yeah, that's a good question. Well, certainly good to share the relevant growth stories. Certainly good to put it into context. Like, maybe the goal was just to turn around. Maybe it was like a declining business, and the goal was to get it to break even. Maybe it was, you know, like a roll-up of multiple businesses, and the goal was just to bring them together, unite, and find efficiencies across businesses and to, you know, cross-sell, upsell, or what have you. And sometimes companies don't grow, and it's like, "Okay, well, this is why." And then not point fingers so much, but to say, "Oh, we had a product problem, you know, we had a churn problem, and we decided to focus more on this other area of the business" versus just plugging the leaky bucket — put it into some strategic context that can be helpful. And the strategic context can also be, "Oh, you know, the overall market for —" I just got off the phone with somebody, and it was like, "Oh, the overall market is a disaster for what we're doing, and we're growing, but it's only 10%." Well, that's pretty good in a down market.

Drew: So I think this is an interesting moment, because when the tide is rising, when everybody's growing, life is easy, and marketing gets credit or doesn't, but it's fine. But right now, it's a very tough market, particularly for SaaS, and there is a very good chance that if you have a role, there is a churn problem and there may be a product pricing problem and there may be a product-market fit problem. I think the thing that I want to just sort of emphasize at the moment is: stop everything and help fix that. Yeah, because the story that you're going to be able to tell, if you don't do that, is going to be harder to tell, right? Because you won't be able to say, "I have a growth story." So: "Yeah, we stopped everything to fix the product" or "We stopped everything to stop churn, and this is how we helped do that." 

Erica: Right. Or "I gave my budget to customer success so they could, I don't know, hire a customer marketer on their team and get ahead of, you know, some of the churn issues," for instance, yeah.

Drew: So every single job that you have or are in right now, you have to be conscious of the story that you plan to tell to your next prospective employer. And it's pretty simple in that way, right? And if you don't have a story because you weren't able to get through the product issues or the sales issues or whatever — it won't save you. It won't get you your next job, necessarily. So all right, so moving on from that. We'll still get to AI, but not yet. What are, in your mind, the non-negotiables you're seeing in CMOs who actually get hired today, and that will still matter as we move forward into 2026? Must-haves.

Erica: I think humility is one — kind of a soft skill. I was talking to somebody the other day who said, "Wow, I spent decades building up my knowledge base. It's hard-won, and it's very hard, like, emotionally, to embrace being a beginner again, but that's what I'm learning to do." And that just stuck with me, like, yeah. So there is that — like you were just talking about — taking that "business first, marketing second" kind of view, which can be helpful in sharing that. And maybe you were in a business that wasn't growing that much, and you could say, "What I would have done, or what I advocated for, and what I learned through that process is X, Y, Z." And again, that kind of experimentation mindset. Having a reason to be interviewing with the company that you are meeting with. I have started hearing from candidates that some recruiters are reaching out and they feel like they're just filling a slate, and it's like, "This doesn't make sense. This role is not right for me." You know, like you said before, companies — especially now — are not going to squint to hire somebody. So if it's a mismatch, maybe the recruiter doesn't totally understand your background. Try to get out of it early so you're not wasting cycles on something that is unlikely to bear fruit.

Drew: Yeah, and we have something called the Huddle Buddies Playbook — one of the last steps is defining, you know, if you look at all the things in your last two jobs that were, you know, the category and the sales structure and the size and the backing — is it PE or VC, or public or private, or whatever — you make that list, you create a grid of 25 folks. Those are going to be your high ICPs, right? And then everything else is going to be a maybe. And it really helps to, as you said, have a reason, so that you don't. And it's also frustrating if you go for a job that you just aren't going to get. And you know that from the beginning.

Erica: It's great to have your list of target types of companies or target people. For some people, they target, like, CMOs. I always recommend to people: have your kind of networking roadmap and then share that with people when they say, "How can I help you?" You just show them your roadmap. And maybe it's like, I don't know, SaaS companies in the FinTech space, or SaaS companies in, I don't know, Charlotte, North Carolina, or whatever, however you're structuring it — and then they will start marking it up. Like, "Oh, actually, I know somebody here. Oh, if you're talking to this company, you should talk to this other one — they just got funded," you know? So that can kind of help people help you. 

Drew: Yeah, I think that's a whole special art form these days. I mean, not only giving — I noticed that you were connected with XYZ. "Here's a note. Would you mind sharing this note with this person?" I mean, you can really push it forward to make it easy for people to do that — share for you. So humility in this beginner's mindset — I think there's like a Japanese term for that beginner's mindset — that's great. Business first, marketing second, and someone who's experimenting and obviously embracing AI. So let's just talk about that. Right now, are you seeing expectations from CEOs change in terms of what they think a CMO should understand and be able to do with AI? And what are the sort of implications or tests or things that you're seeing CMOs face?

Erica: It's not as clear. Usually it's more like, oh, we want to hear about AI. We want you to have a perspective on AI. We want you to be kind of testing it out. We want you to be, ideally, having some efficiencies with it. Again, I haven't had anybody say we want somebody who's ditched their whole team. I mean, if you do have those examples of, like, oh, well, I just talked to somebody the other day. We did this big, I don't know, brand relaunch, and we used to have, like, videographers, and now we're able to do these very quick, you know, videos for it, and then we, you know, slurped out the content and made the sales enablement material that was very personalized, and it all took an hour. And blah, blah, blah, yeah. I mean, that's a good story, you know. It's a totally, you know, credible story. So I think it's a plus. But what I see is companies, they're asking for efficiency overall, and if AI is part of that, that's great. But if you're just doing crap with AI, just buying tools — like, you can spend a lot of money on these AI tools — you know, if you're just doing that, and you're not, you know, kind of focusing on the priorities that the CEO and the, you know, investors, if they're there — if you're not delivering on that, that's going to come out sideways a little bit, yeah. And this might be different if it's like a natively AI company, right, that is really looking for, you know, a different kind of skill set. I did a podcast with Kathy Sreenivasan, who she just joined — I think it was Freshworks. Yes, if you look at me on my podcast, I did something like "AI native CMO" or something, so that's something else to look at.

Drew: Yeah, I mean, I'm hearing that there is no such thing as a non-AI-proficient CMO getting a job. I think there's a certain level of expectation that you understand the tools, that you have at least an approach, that you have experimented — and more than that, experimented and piloted — with some real benchmarks, who are saying we're going to change our workflow. And it used to have 50 manual steps, and now it has three, right? Yeah, and being able to tell those stories. I think we're beyond, you know, "yeah, we used it to create some copy." I do think there's — we're getting to this place where lots and lots of CMOs are creating tools, whether it's a complete brand set or a complete GPT for sales or, you know, all sorts of things that are just not that hard to do. And so, yeah, that's happening. Okay, yeah. So we talked a little bit about mindset, and we've also talked about this "not squinting," as you call it, which I think is a funny expression. In any of your placements in the last 12 months, how many of them were perfect square peg, square hole in terms of experience — like, their last job was just like this one, or they took it from 50 to 100 — or were there some flexibility in some of those? And if so, what were the standout characteristics of those who managed to secure jobs that didn't look exactly like their last one?

Erica: Yeah, that's a great question. I did place somebody where from the get-go the company was like, we're all about the partner motion. We want somebody who has built marketing through a partner motion, a partner motion, blah, blah, blah, blah, blah. I found this gal, and it was a VP role, and I found her, and she was a CRO at a company. She had been a CMO. She was, like, recently a CRO. And I was like, I don't know, this might be a little junior for her, but, like, she had worked in relevant businesses. Let me just reach out, and I'm talking with her. I'm like, God, this gal is fabulous, like, great revenue growth stories, and just had a lot of credibility and everything. And I said, well, tell me about the partner thing. It's a bit of a minor thing. I mean, she was honest, like, it hasn't been as big of a thing. And so I just put her forward. And I was like, you know, okay, here's the deal. I really like this gal. Like, I hate to say I work on gut, but I have been doing this for a long time. And, you know, just when people stick out, they stick out. And I'd been working on the search for a little bit of time, so I kind of, like, culturally, felt like it would be really great, and I put it forward. And I was like, okay, you know, here are the things where she doesn't quite line up, and the CEO, like two minutes later — and it was a Sunday, right, right — oh, I'll meet her. I'll meet her, right, right. And then, boom, boom, boom. And now she's in the role. And then they upgraded the title from VP to CMO. It's interesting. She didn't even ask. There you go. They just came back to her. I mean, she was really strong.

Drew: This is on the strength of you and your reputation and your relationship with it, that you can do it. And this is the thing — I was talking to some CMOs on this call, I think, earlier today — and talked about, there are the rare cases where a recruiter will be able to place you in a job that doesn't have the 10 by 10 match, right, or the six by six match, but it's based on your insight into that individual and being able to put forth them as a great candidate who might — "this doesn't check this box, but is a great candidate and a great cultural fit, and you're gonna like them." And just trust me.

Erica: I mean, I talked about 11 out of 10 requirements. I don't think I've ever placed somebody where it's been like, absolute — there's always question marks, right? There's always, like, a lot of things that are strong, and there's always some question marks, and it's just about what companies value at the margins and what trade-offs they are willing to make. It ends up being a vibe for a lot of CEOs. Like, I know, like everybody talks about being data-driven, but, like, the vibe matters a lot. And also you often set up kind of, like, a criteria framework or scorecard kind of thing at the beginning of a search, and then you start going through it, and you realize, oh, actually, maybe this doesn't matter as much as this. Like, maybe just being experimental, really, you know, matters more. Or, you know, oh, this thing, we just bought a company and so that fills in this product gap. So, blah, blah, blah, you know, like, it's kind of like a jigsaw puzzle that's changed. We just hired a person, and they're strong in demand. So maybe we pivot more towards somebody who's done, like, you know, kind of more the positioning stuff. I always tell people, like, it's kind of like getting married. I hope my husband doesn't hear me. But like, you know, you marry somebody, you think they're 10 out of 10, they become an eight out of 10 over time. And so just realize that it's going to be an eight — like, if you have the eight out of ten, like, that's probably good. The challenge, I guess, if you're a CMO candidate, is, like, you could have companies where they have multiple candidates that are, like, eight out of 10, and it's just like, what are the eight things that they're really gonna value?

Drew: Yeah, so it still comes down to gut. One of the things — this is a two-way process, right? And a CMO that's interviewing for a job wants to maximize their chance of success, so there's a discovery process that they go through, obviously independently, and then when they finally meet the CEO. Are you — meaning this may apply to you and whether or not you'll even do a search — but there are CEOs, and there are CEOs, and some are really great leaders. And I was talking to one last week who is like, the CEO and everybody else on the executive team are all players, not coaches — like, they are in the weeds, they are doing — and the company is at $75 million; they should have been beyond this. So what in your mind — how do you know? Are there behaviors of a CEO that sort of come out as red flags that CMOs can screen for, or that you screen for?

Erica: When I'm talking to somebody about doing a search, I usually try to challenge them on something or change their mind on something. Oh, you think you need somebody who's a career product marketer — I don't know, because I'll recruit VPs of Product Marketing too. You think you need somebody who's a career product marketer, but what about if you had a CMO at a smaller company who now wants to, like, dive into product marketing at a bigger company? How would that feel to you? Or here's the benefit of that, because, you know, they could kind of, I don't know, see around corners a little bit better. That's a softball one. But you know, there's other things where I'll, like, challenge, like, oh, how would you really — why is that really important, you know — and I'll see how they react to that. And if they get really defensive, that's a bit of a, you know, a tell for me. I think also the willingness to do trade-offs, like, I have this slide, and it's all about, like, trade-offs. Like, if you think you want the person who stays for a long time and doesn't have short tenures — well, beware, because sometimes the person that has been in their company for six years is going to misstep the next time they move. It happens more — like you, just experientially, like you'll, you'll see it happening, you know, because you're used to, like, the weather being warm and sunny, you know, in one place, and then you're not, I don't know, maybe not attuned to cultural stuff. And so that's a trade-off that, like, you know, I try to talk with people about, like, okay, you really want the, you know, really quantitative, analytical person — well, that person might not be the best in front of a room, you know, maybe not. They won't be the best evangelist for the company, okay? And if they absorb that, I think that's great. From a candidate standpoint, the thing that I've been thinking a lot about lately — it's fascinating — the recruiting process matters just as much to some candidates as the job does. So I had a situation where I called somebody. She was like, oh, yeah, I'm only talking with you because I know you, and I — yeah, but you know, I've had other recruiters call me and they don't really understand what this is, and I want, you know, I want a whole good recruiting process or something. And I was like, that's interesting. Would you say no to buying a house because the realtor for the selling agent was a dork? And she was like, well, I might, actually. And I was like, oh, fascinating. And I think what it is, is that candidates want, kind of, like, a fast speed of trust. Like, they don't — you know, obviously clients, or, you know, CEOs are trying to be very cautious when they hire. But like, how do you be, like, thorough with hiring, but also, like, get to that moment of trusting somebody and feeling like, this is a peer-to-peer conversation. You know, some CEOs get too into, like, oh, let me just grill you forever. Or more. But the ones that candidates tend to like more is when they walk in and there's a lot of, you know, kind of trust for them, and where the recruiting process is really strong. So that's been interesting to me, maybe just because there's, like, there's so much uncertainty in the world, and, you know, we can look at a recruiting process and, I don't know, evaluate it.

Drew: So what's a strong recruiting process? What's a good one? How do we even know what that is? What is that right now?

Erica: I'd love to hear from this group, you know, maybe in the chat — like, how do you like to be contacted for roles? How personalized? Like, I don't know. I'm very open to it. I think a strong one is where people don't feel like their time is being wasted, where it's transparent. Sometimes you can't be super transparent, because sometimes it's like, okay, well, they're still thinking, they're still meeting other people, and I don't know, it's always hard. I've started doing videos with CEOs to kind of, like, have a teaser about the opportunity — like, a 10-minute interview with me. And just like, what you and me are doing here, Drew, like, just a quick — it's more like 10 minutes, but like, you know, what's the opportunity? What's the market like? What are the customers like? What's the culture like? Those have gone over well. I'm, you know — no recruiting process is perfect. What's funny is, you can have the same process across everybody. Some candidates love it, like, oh, I love taking behavioral assessments. And other people are like, no, I will not do a behavioral assessment — like, I'm out, right?

Drew: And I know that because you do a lot of PE firms, there are a lot of PE firms these days that are doing behavioral assessments — that that's just the price of entry. So, and I also know CMOs who've prepared like, taken — like you did for the SATs, you know, prep courses for them. 

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Drew: I find more and more this — so a CMO will call me and say, hey, I've got three offers, and they're very different types of companies, because they seem to breed — you go into a blank spot, and then suddenly you have three offers, and how to evaluate which one. And I make it really simple and just say, it's the CEO, stupid. If this is a CEO that you trust, that you can work with, that you think will — and your expectations are aligned — life will be as good as it can be in a CMO role. And if not, it will be terrible. Am I oversimplifying that, or in your experience, are there other factors that sort of accrue to a CMO's success, even if the CEO relationship is just modest? 

Erica: I think that's decent advice, Drew.

Drew: You can tell me I'm stupid. It's okay, I can handle it.

Erica: I think that's true probably more often than not. I was just thinking, sometimes CEOs get replaced. So you hire — you know, you join a company for a CEO and then — but that could happen anytime. 

Drew: And by the way, when that happens, the new CEO comes in and gets their own CMO, so you are screwed at that moment. So you do — so you are. And then I've seen it — literally last week it happened. So new CEO comes in, boom, you're gone. Even though the growth story was there, everything was there, the sales relationship was there. People were shocked. But nope, new people. So it happens, and it happens more than you would want. So I guess the only — and there's no protection against that, other than, I guess, talking to the board and saying, so, what do you think of the CEO?

Erica: Yeah, right, right, exactly. And do they have a heritage of turning over CEOs? And has that CEO done the scale-up the company is looking to do before? Are they a first-time CEO, a founder? Have they been there for five years? Maybe they're getting tired. Are they really excited? Have they, you know, whatever. I would say, it's also like, look at the culture. There's that, and then it's kind of incumbent on both sides to not just feel a vibe — even though we talked about so much, like gut — but to actually ask good questions about culture. Like, what is — sometimes I ask people, like, what is a, you know, cultural pet peeve you have? What are values you grew up with that are really, you know, important and, you know, imbue your work now? Like, what do you — or ask a CEO, like, what are things you value? Again, it gets to trade-offs. What do you think? What are the things you value more than others? Like, okay, we value perfectionism so much that we are willing for things to be — or, you know, we value getting things right, and so we're willing to have things be a little slower. I don't know, that's a cultural aspect of peace that I think is really important.

Drew: Is there anybody saying slower?

Erica: I mean, again, there's the "get it right, get it done right." And some people are more like, hey, we want to really make sure we are, you know, ship shape. And, I mean, that's a little more unusual, but right, sure, sure.

Drew: So there's this interesting moment where, as a CMO is getting to know this company — and obviously you can do a tremendous amount of research, and you can create sort of GPTs that do their assessments and go out and scrape all their analyst reports, and you can find a lot of interesting facts — and you should do all of those things. And as you get more confident because you're finding out all this information, you may feel like, oh, yeah, we can solve this problem, right? And then you may actually say, yes, I think if we can solve this particular set of problems that you've described, where's the balance between sounding confident without overpromising? Yeah, because you don't really know until you get there. Oh, our sales guys are really sucky, or our product just doesn't compare, or our customer service is really underdelivering?

Erica: Yeah. I mean, I think companies appreciate it when people don't just look backwards to what they have done, but look forwards to what they would do. They love it if somebody is going to do a little bit of kind of prep work. And maybe this is not interview one, maybe this is like interview three. Like, okay, well, I've been thinking about what you said, and here are the themes that came up. And here are, like, the top three things I would do in the first, you know, I don't know, a few months or whatever. And if you share your assumptions, you know, that makes it, you know, even better, if you have a conversation about what would make this happen fast versus slowly. Because that's, I think, where CMO and CEO partnerships can fail. It's when there's misalignment between what happens in the short term and the long term. Like, expectations can be like, oh, wow, you know, you're gonna, I don't know, flip some things, and then we're gonna get, like, 2,000 leads next month. And that's, like, way bigger than, you know, we were getting too early, you know, whatever. So managing that process and saying, this is faster when XYZ happens, this is going to be slower when, you know, ABC happens — that can be better. And the other thing is, sometimes people — often, you know, candidates are asked to do presentations and stuff, and people can grumble and, oh, it feels like free work. However, it could be a good way of really feeling like, is there that fit there, and companies are very understanding that you're going to get half of that wrong.

Drew: Right. I like to sort of — I think once CMOs framed it as, here are my three to five working hypotheses going into this. These are the things, like you talked about assumptions. I like this notion of hypothesis, because that's a thing that you can test. Yeah, these are, these are the working hypotheses. This is where we get to the gaps that I think we could fill. Here's how I can sort of find out whether to verify these hypotheses, and we can do it in the first three months. The short-term, long-term thing is so problematic. And I wonder, particularly in PE firms, where, depending on where they are in the sales cycle of the firm, it's like everything is short term. Have you met some candidates that are really good at sort of helping a CEO understand that, hey, our product perception problem — you can see it on G2 and TrustRadius. You can see it with the analysts. We're not going to fix that in three months. And if we don't fix that long term, our sales are going to continue — we're going to lose more deals. Our churn rate is going to be higher. So I know you want more leads now, but we've got to fix this first. Have you met some CMOs that have made that argument successfully and actually bought the time they need to solve the real problem?

Erica: Oh, good question. A lot of them are — I mean, maybe some exist on this call — but some of them are like, the strong ones will say, yeah, you deliver on the short term while doing the long-term stuff. You might not talk about some of the long-term stuff in a board meeting or what have you, or you might not showcase how much time you're spending on each, but you have to have the empathy for the fact that, like, you know, this is a company that might be planning to sell. There might be things, especially before you join, that you don't know — like, oh, the company's in conversations to get bought, or to roll up with three other companies, or, you know, what have you. And so there might be a good reason why getting those oars in the water fast, you know, makes sense. And that's also, like, if you're talking ahead of time — and I think you can have those conversations, like, are you aware that blah, blah, blah. But I also think that's a kind of adversarial way to put it, like that also gives the CEO a problem, you know. So I would — what you said, Drew — I would extend that to be like, so here are the options: we could focus here, and this is the results we're going to have. We can focus, you know, on longer-term stuff, and then that's going to take a little bit more time. We can put some resources over here. We can try to, like, put lipstick on a pig, and, you know, that could look like this.

Drew: So we have some questions that I want to just make sure we get to quickly. Red flags — in terms of what you see on both sides — things that make you tell a CMO, don't take this role, or tell a CEO, this candidate isn't the one. I mean, obviously you wouldn't present a candidate if they aren't the one, but I imagine at some point in time there has been a candidate or two where you're going, yeah, I think we should move on. This isn't the right fit for you.

Erica: Yeah. Well, I think we talked a little bit about the red flag on the CEO side — like, oh, I think I know it all, and I'm not going to be persuadable in a process, or I have, like, unrealistic expectations. On a candidate side, sometimes there's just odd behavior that can be a little red-flaggy. The other thing is, like, if a candidate takes a long time to get back to you or to draw out the process, you wonder, do they care as much, and is their speed going to match the speed of the company — especially now, when there are candidates that are like, yeah, I'm excited about this, and I've thought about this already, and here are some work samples, and here's how I would tackle the role. And then, you know, you might have somebody else — and it's okay. Like, I always say, if there's a chance you're going to take the job, have the conversation. I am totally fine talking to somebody and having a couple of conversations, and then being like, oh, it's not the right time, it's not the right fit — that's fine. But yeah, try to, you know, match the pace, and try to, I don't know, be a real person. Be authentic. I think maybe another red flag, which could be relevant here, is that I think there's a lot of trauma in the CMO community. So I think that sometimes people can be a little raw emotionally, and that can work for you or against you. Like, I had somebody almost in tears one day, talking about her team and how she had built this wonderful team and that she had left the team — it was actually quite lovely. And then I've also seen people — maybe not CMO level, but more VP level — that'll be noticeably nervous in an interview. And so that, especially in a PE-backed situation where you're going to have people being like, where are the numbers, and let's defend your budget — that would be, you know, that's a question mark.

Drew: Yeah, you have to exude confidence, because you're gonna need that. I mean, it really is something. It's a job where, as a leader, if you can't be confident, nobody's gonna have confidence in your marketing. So it does feel like that is a — if you're nervous, that's going to be hard.

Erica: I would say it's authenticity. Like, I also don't want the overconfidence — authenticity being like, oh, I'm still working on this, I'm struggling on, you know, this. I think I love that.

Drew: So do you go back to the CMOs that you've placed, and if so, are you getting some reality checks from them in terms of the job they thought they were getting and what they actually got?

Erica: Yeah, I do stay in touch with people and, you know, text them like, how's it going. I mean, some more than others — sometimes I make friends with people more than others. Or, like, location, you know, can matter. People are often doing better than they think they're doing, because they also stay in touch with, you know, CEOs, investors — like, in some PE shops, they have marketing operating partners, so people who are like a bridge almost between, you know, the portfolio company CMOs and the PE shop. These people can be great anyway. And I'll be like, oh, hey, how's so-and-so doing? And they're like, oh, they're doing great. Oh, wow, they're fabulous. And this, I mean, it's not everybody, but, you know. And then when I'm next in touch with the candidate — with the person I placed — I'll be like, hey, I heard you're doing really well. And they're like, oh, really? And so, I feel like, yeah, I don't know, I guess I'm honored to be able to do that for people. But yeah, maybe expectations are so high that people don't want to, like, just, I don't know, take time to be, you know, a cheerleader, right? But yeah, sometimes people are like, whoa, this is a bit of a cluster, you know. Like, wow, this is — I didn't realize that this change was about to happen, or, you know, and often it's like, oh, I didn't realize the sales leader was on their way out, or, you know, what have you. And I mean, I have a pretty strong placement rate. I did, like, an analysis on how long people stay in their roles. I had a guy stay for six years, a woman stay for five years. I've had more people stay for three years. I've only had to do a replacement search once or twice. This is because there's a lot of work that goes into it.

Drew: I know a number of CMOs in the transition team — our program where we meet a couple of times a month and get folks like you to come back, as well as people who've landed jobs to come back. And a few start to get really self-conscious about the fact that they've been out of work for three months or six months, and it's hard. And yet there is this moment where, because they're out of work, they could start right away. And this notion of readiness and availability — in your mind, does that play at all in any of the searches? Where someone who's been out of work for a while, that's an advantage to the employer, and the employer actually sees it — yeah, they could start tomorrow. Or they could start as a, you know, a fractional.

Erica: Yeah, I mean, you just said it, right? So sometimes speed works in your favor, because you don't have to go through a whole process of, like, giving notice and transitioning your work or staying for a bonus. Like, especially this time of year, people are like, I got a bonus at the end of March, and so I can start something new, but it's going to be May, or, you know, whatever. I think companies — there's less stigma than there used to be about people being kind of actively looking. You know, companies are just like, hey, we're busy, we want to find the right fit, and if this person works, all the better. A lot of people will say, like, oh, hey, I've been taking some time off, you know, I've been working constantly for, like, 25 years or whatever, and I was able to, I don't know, travel to Australia, or, you know, whatever, right? And, or, you know, people have kids, or, I mean, life happens. And I think we understand that life happens. So I think it can be helpful, especially, like, now in the PE-backed settings that I'm dealing with — something like, I just wrote to a bunch of candidates last week, and they were like, this sounds great, Erica, but my company is going to exit in the next couple of years, and we're doing fine, we're doing well, and so the timing is just not good. And so, like, especially if you've had an exit and you're just taking some time, and maybe it was a financially juicy exit, people would understand. I think the other plus is that you can be kind of taking your time to, you know, lean in on all the new AI, you know, kind of learning that people who are actually in-seat might not have time for.

Drew: And it's true, and I've seen that in real time. I love that the British have an expression: garden leave. I love that expression. And some Brits will put it on their LinkedIn profile — "garden leave" — this year. And, you know, there's this slight difference in that they had a one-year non-compete, and so that was part of it. So, all right, well, we promised a pep talk. We haven't necessarily given one yet. Let's try to shape some of the things that we've talked about into a sense of optimism, or things that CMOs can do to improve their chances to get a job in the next six months.

Erica: Yeah. I mean, companies — they want to know you. They want the authenticity, and they want the numbers. You only need one role. And I've known a bunch of people who are out for a while, and then they land really meaty, interesting jobs, and they look back and it was a blip. When they're in it, it's hard. I have a friend — I might have shared this in the last one, Drew — but I have this friend, Cesar Brea, great marketing analytics consultant. Anyway, he's like, you're never as good as you feel when things are great, and you're never as bad as you feel when things are not going great. And I think about that a lot, just because I'm in executive search, and it's the highest of the highs and the lowest of the lows. Like, you're always dealing with that. So that's something that I think people can think of. And I also think if you're between roles, you have the opportunity to prepare and get to know different companies. And it's kind of cool looking back — like, wow, I met all these companies, I learned about all these different areas of business, and, you know, the economy, that I wouldn't have learned, and I made new friends. And, you know, might not see it now, but maybe in a year it's like, oh, wow, this person I met, you know, for this thing, and it didn't go anywhere, but now they're calling me up to be an advisor for blah, blah, blah. They're introducing me to my next, you know, I don't know, CEO, or my next director of demand, or what have you.

Drew: You only need to find one — that's, I think, the key takeaway here. And we talked a little bit about how to try to focus your outbound search and manage your inbound search so the ones that you are competing for are ones that you have at least a decent probability of closing. I wanted to ask — first of all, folks have asked, where can people find you and how should they engage with you ideally?

Erica: LinkedIn. I also have a newsletter that I, you know, occasionally put out, and I'm just plunking my email in the chat right now. Oh, that just went to Nicole. Sorry, Nicole — it's so funny. I do these and I see people that I've talked to before, and I'm like, okay, cool. And so yeah, you can connect there. I also have my podcast, which is on hiatus right now, but should start again in the summer.

Drew: The joys of being a solopreneur.

Erica: Oh my god, yeah, yes, yeah.

Drew: It's a relevant point here, because essentially everyone else who is between opportunities or in transition is a solopreneur tour, and it's interesting. And every day, you're making choices on the time and how you spend it. We are very grateful that you chose to spend it with us today. We hope you got some value out of this. If you're new to CMO Huddles and the transition team, we are having conversations like this every two weeks, and we are really dedicated — overall at Huddles, we like to say, help CMOs win. Well, when it comes to the transition team, it's not just landing a job, it's making the process a little bit more palatable. It's a painful process. And our thought — not a new thought — is that if you're doing this alone, you've created a very painful island. And so find a community — if it's not ours, somewhere else — where you can come together with people and share. Yes, you can query the bots and say, how'd I do? But having another person to prep with, having another person to troubleshoot with, is really going to improve the odds. And so the last thought I want to give you all is: you are professionals, kind of like professional athletes. Are they your marketers? Professional athletes are constantly looking at their swing or their approach or the tiniest little thing. And so I really want to encourage you all to find a buddy — we call them huddle buddies — to help you refine that little thing that may keep you from getting your next opportunity, the one that you really want. So thank you, Erica, so much for joining us today.

Erica: Thank you, Drew.

 

Drew: If you're a B2B CMO and you want to hear more conversations like this one, find out if you qualify to join our community of sharing, caring, and daring CMOs at cmohuddles.com.

Show Credits

Renegade Marketers Unite is written and directed by Drew Neisser. Hey, that's me! This show is produced by Melissa Caffrey, Laura Parkyn, and Ishar Cuevas. The music is by the amazing Burns Twins and the intro Voice Over is Linda Cornelius. To find the transcripts of all episodes, suggest future guests, or learn more about B2B branding, CMO Huddles, or my CMO coaching service, check out renegade.com. I'm your host, Drew Neisser. And until next time, keep those Renegade thinking caps on and strong!