September 28, 2023

Ace the Interview: B2B CMO Edition

“Tell me about yourself.” This vague, clichéd interview question can be answered in a lot of different ways. Executive coach Jacob Warwick is here to tell you the best way, especially if you’re looking to land your next CMO role.

In this riveting CMO Huddles Career Huddle replay, Jacob shares his top interviewing tips and tricks, like how to be assertive, why you should lean into your competition, and how to approach compensation conversations. For those eyeing the CMO chair – a position known for its fleeting tenure – this episode is essential listening. Immerse yourself and gear up for success!

What You’ll Learn

  • How to align your skills with the goals of the org
  • The top mistakes made in executive interviews
  • How to approach the compensation question

Renegade Marketers Unite, Episode 364 on YouTube

Resources Mentioned


  • [3:44] The trap of: “Tell me about yourself”
  • [7:59] Finding future alignment
  • [9:52] Common components of a compelling interview
  • [15:37] Testing the waters with the CEO
  • [18:19] The top mistake people make in interviews
  • [21:54] Assertiveness vs. arrogance
  • [25:56] The 30/60/90 problem
  • [31:13] Aligning with interview stakeholders
  • [37:42] Do these same strategies work for women?
  • [40:06] Leaning into your competition
  • [43:15] Don’t share your compensation number
  • [48:57] Two dos and a don’t: Interviewing for a CMO role

Highlighted Quotes

“Alignment is more important than being impressive.” —Jacob Warwick @thinkwarwick Share on X “Ask open-ended questions to see the direction that they're interested in heading in. It tells you exactly the info you need to tell the right stories in the right context and move that interview forward.” —Jacob Warwick @thinkwarwick Share on X “As CMOs know, sometimes people see marketing as a line-item expense and not an investment, so we may want to ask some questions to challenge that thinking along the way, too.” —Jacob Warwick @thinkwarwick Share on X

Full Transcript: Drew Neisser in conversation with Jacob Warwick

Drew Neisser: Hey, it’s Drew. And I’m guessing that as a podcast listener, you will also enjoy audiobooks. Well in that case, did you know the audio version of Renegade Marketing: 12 Steps to Building Unbeatable B2B Brands, was recently ranked the number one new B2B audio book by Book Authority. Kind of cool, right? Anyway, you can find my book on Audible or your favorite audio book platform. And speaking of audio before we get into today’s show, I do want to do a shout out to the professionals that Share Your Genius. We started working with them several months ago to make this show even better, and have been blown away by their strategic and executional prowess. If you’re thinking about starting a podcast or want to turbocharge your current show, be sure to talk to Rachel Downey at and tell her Drew sent you. Okay, let’s get on with today’s episode.

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 Neisser: Hello, Renegade Marketers! Welcome to Renegade Marketers Unite the top-rated podcast for B2B CMOs and other marketing-obsessed individuals.
Welcome to our second Career Huddle. This one features Jacob Warwick, and we’ll explore his interviewing and negotiating expertise, which I have to say is kinda awesome. I’ve had a chance to speak with Jacob several times now in the last couple of months and have no doubt his recommendations will kind of be a game changer for those of you in the hunt for a new role today, or in the near future. Hello, Jacob. How are you? And where are you?

Jacob Warwick: I am in upper northwest Montana. And I have a three month old infant who has slept perfectly since he was two weeks old. Except for last night. Drew I know we were just thinking about that a couple days ago. And I’m with bragging, he’s always perfect last night woke up three or four times. So of course, the one time I have an important event. The potty schedule was off, throwing up, all the good things that parents get to look forward to.

Drew Neisser: Northwest of Montana makes you the first guest that has actually been live from Montana. So that’s exciting. I feel like you’re practically in Canada.

Jacob Warwick: Yeah, actually it’s a stone’s throw to Canada about 40 miles from the border. Sun goes down at midnight in June. So we get that. But about 25 years of my career was in San Francisco and in the tech Silicon Valley ecosystem and out in New York and LA. So don’t let the cattle farming fool you.

Drew Neisser: Okay, let’s get right into this. We talked about this in our prep call that a lot of interviews, start with this question which you and I called a trap, which is the, “Tell me about yourself?” What’s the best way to handle a question like that?

Jacob Warwick: Yeah, the tell me about yourself is not always asked exactly like that. But generally speaking, always, everyone’s going to want to know a little bit about you in the right context. And the trap of that is that the question is so vague, that you could steer it in many different directions. So some people will enjoy the more personal effects about you like, “Hey, you have a son, I have a son, you live near the border, I live near the border.” Whatever that may be. Or some folks—and traditionally, this is what happens in a professional interview—you get closer to, well here is the chronological order of my career and all the professional aspirations that I have in an ideally shortened sense, but oftentimes will ramble into 10-15 minute territory and just keep going and going and going and the wheels fall off. So I like to push back on that question and get more specific and oftentimes provide a preamble of almost like the agenda of what you’d like to cover about yourself and what actually interests the other person in that context. So you might say, “Hey, if you want I could start back in college but I’m sure you’ve heard that several times. So I’m going to truncate my experience on what I think is most appropriate for you and the mission of your company. And I’ll share a little bit about myself, my family, and some of the things that are important to me, and then move on to ask some questions.” Sometimes I’ll even ask permission like, “Hey, is that the outline of what you’d like to see covered today?” So providing a little bit of boundaries to something that’s so broad and vague to keep yourself focused in the right direction. And to reiterate that through a verbal affirmation to make sure you’re on the right track every step of the way.

Drew Neisser: One of the things that I have noticed, particularly with folks in transition, is that they feel the need to explain why they’re not at their last job, often from almost defensive mode. And I’m wondering, especially appreciate the notion that this is not a chronology, they are listening for signals that say, this person aligns with what I think we need for the company to move us forward. So how do you make sure when you ask such a vague question, and I know you’ve qualified it down, but how do you get to reframe the answer in a way that you can talk about a specific experience and have them see through that experience, “Oh, okay. Those are things I’m looking for.”

Jacob Warwick: You know, how everyone’s surface level interview advice is to do your research. You go to the website, and you look it up, you’re looking at people you might report to, or maybe the stock performance or any details about the company. What often happens is in the interview process, you say, “Well, I did my research, and I saw these things.” I guess one way of saying yes, you do your research ahead of time, you’re looking for a shared identity that you have with them, whether that come from your experience, and what they’re looking for some of the challenges that they’re facing, you’re applying your experience to their needs, in some capacity. We should do enough research to be able to make some assumptions on what that company may be going through to show your expertise. Several of the folks on this call actually know offline out of CMO Huddles as an example, some of them are startup experts. And they’ve gone through a certain iteration where generally speaking, the same go-to-market strategy is roughly applicable. So you can make some assumptions on what a company may be going through. I think the key piece here is that it’s more important to find alignment with the company than it is to be impressive with your background. So if you don’t know where that alignment is, don’t just say, “Hey, these are all these impressive results I had for my career.” It may not matter, or so much time has passed that a company may be going through a completely different set of challenges, and you’ll miss the mark. So if you don’t know exactly how to find alignment through that, that means you need to ask more questions. You either didn’t discover enough through what was publicly available through your preparation but now’s your second chance to do that based off, “Hey Drew, was this conversation going the way that you had hoped? Am I covering your agenda items, or perhaps you could share an agenda on what’s most important to you. My hunch is that at this stage, go-to-market pretty important, your early stage, you’re trying to grow or your pre IPO and you need to maximize the processes.”

Drew Neisser: Alignment is more important than being impressive. I’m wondering if you could give a real example of that?

Jacob Warwick: The person that you’re interviewing with has a software product that is involved with Salesforce as an example, you know that to be true. In my past experience, I’ve gone to Dreamforce events, I’ve drank the blue Kool Aid, I’ve been in the Benioff tower, whatever it is, now I could create some alignment just to show that I understand the ecosystem of the environment that they sell into in some context. So you might tell a story about I went to Dreamforce in 2014, and 2016 did the booth thing, a different companies time, whatever it may be, just to show that you’re at least acknowledging the same shared identity of that ecosystem, as an example. What’s interesting is, and this is where I think the alignment is more important to being impressive, doesn’t matter if I’ve been to 15 Dreamforce has already know how many there’s been, what I’ve done in the past doesn’t necessarily guarantee success for your future. So I want to see alignment with the direction that you’re going here. So as I’m building that shared identity in the past, I’ve been to the Dreamforce, I understand Salesforce, whatever, that’s just showing that you can trust me that we can speak on a higher level and get a little deeper into the weeds as necessary. Now, what you may say is, “I’ve seen some things that worked, can you tell me a little bit more about what some of your challenges are in the next 12 months?” So the trick with these, as we find alignment, we don’t want to find past alignment, we want to find future alignment. What you’ve done in the past, and a lot of marketers specific, especially C-suite marketers and CMOs, in order to get to the position of power that you’ve been in at your organization’s you’ve had to be pretty forward thinking and growth mindset oriented. And that is directly in contrast to what a lot of recruiters look for, which is, has so and so done this before? And so you’re a growth oriented, you’re like, Hey, do you want to do this, again, you’re trying to find future alignment and growth. So we need to communicate towards a future state and see if we still have alignment with that company in that regards too.

Drew Neisser: So future state. So you’ve done your homework, you realize that they’re in full growth mode they’re trying to get from 25 million to 50 million And that means you’re going to need a team of five, you’ve led a team of five, what are the common components of a compelling interview, and maybe that will help us frame this.

Jacob Warwick: Sometimes it’s commiserating with the challenges, whether you have the solution or not just to recognize, let’s say you set a team of five, right, or several books here that have led at least a team of live. You might talk about some of the challenges that you had prior in that growth stage. And you might also say that man, we concentrated on this for about two years, we were racking our heads against the wall, trying to solve this problem trying to grow through marketing, trying to get our channel strategies, right, whatever it may be, it always felt like we were second class citizens in marketing. And you can even use language to prod and see whether the company respects marketing as high as other functions as an example, in the way that you structure some of those questions. So you might commiserate with the challenges to show that you understand the challenge. And then I like to propose a few alternate solutions just to see where the other person’s head’s at for the future. So you might say, “There’s a couple of things we tried, we tried hiring a junior team and onboarding them. And honestly, that was a waste of time. We also tried outsourcing to an agency, we built some partnerships, we did this, we failed in some of these capacities, which maybe you’ve tried some of these things.” So we’re trying to see like what solutions they’ve tried what you might be able to then hone in on what might be more effective for them. Because something that worked for you in the past may not work for them. So as an example, I hired four people, and this is what the org chart looks like. And it works every time promise. And that a person’s like, “Yeah, we tried that you’re dumb, it’s not going to work here.” You don’t have alignment. So you might want to just explore a couple of options. “We tried this path, we tried this path, found some success. This is what we learned in this context, can you share a little bit about some of the things you’ve tried, and maybe it was timing that was off, maybe it’s this, whatever.” So we’re just asking some more open ended questions to see the direction that they’re interested in heading. And what that does to the process, it tells you exactly the information you need to do to tell the right stories in the right context to move that interview forward.

Drew Neisser: Right stories, right context. So what’s interesting here, and I think there might be some folks that would be reluctant to say, “We tried this and it didn’t work.” I’m assuming that there is something at the end of this story where we try this and it worked really well.

Jacob Warwick: It depends on the context of what you’ve done in your career. Because if you’ve done a bunch of things that haven’t worked in, you had an 18 month tenure or short tenure, CMOs often have a short tenure, sometimes things didn’t work. Sometimes it’s more appropriate to be ultimately pragmatic and honest about things that didn’t work, and that you couldn’t find alignment, what you learn from that, so that you can come in as your most authentic self. Because sometimes you’ll see someone will have a short tenure of like eight months, and then on their resume, they’ll write all of these monumental successes, which may or may not be true. But from a recruiters perspective, how could you possibly accomplish that in eight months, that was probably the rest of the team, you’re riding the tailwinds into success there, you can claim that, but you only lasted eight months, so something was wrong there. You may share that areas where you didn’t find alignment, and you’re learning from that as authentically as possible to determine whether the person is going to judge you for that or find that is ultimately her leaving that you’re honest about it. So I agree that ultimately, you would want to come to some type of logical conclusion where you’ve been successful. That certainly sounds better. It is more appealing. However, even if you didn’t, it’s okay to be really honest, as long as you share, “Hey, these are some of the things that I didn’t think went right. I ultimately wasn’t able to secure the budget that I thought was necessary to go to market in this particular climate. Now, can you share with me how you’re thinking about marketing?” The CMOs know sometimes people see marketing as a line, item expense, not an investment. So we may want to ask some questions to challenge that thinking along the way, too.

Drew Neisser: And ultimately, you’re really leading this conversation, it feels like you’re trying to guide it to a place. You’re discovering things, but you’re also setting yourself up to the fact that you can help this company get to the future state, based on some of the experiences that you’ve had, in the past good and bad.

Jacob Warwick: You’re ultimately going to have to lay your cards on the table in some capacity, and understand what they’ve been doing what’s worked, what hasn’t worked. Unless you’re speaking with just the earliest stage of startups and your very first marketing hire, you’re gonna have the opportunity to fail a lot, and then get fired probably pretty quickly after that, depending on how the startup’s doing. If you’re going into a more midsize or larger organization, you’re going to want to know what have you been doing? What’s working, what’s not working? I’ve tried these things. And this is where the disconnect is. This is what the learnings are. Did you have that similar conclusion why or why not? It’s an exploration. In a sales call, this would be a discovery call. We’re just discovering if there’s alignment here. If we don’t understand their challenges thoroughly, how can you be so confident that you can solve them? So we want to understand, “Hey, that’s a problem. I know how to build up the organization. I know how to do the hiring. I know how to mentor the team up in this context, I know how to work within these confines that can ultimately develop your confidence.” And at least understand, I think one of the tricky things is, in the interview process, everyone’s wearing their Sunday best, everything’s great. I ultimately want to know what dirty laundry I’m stepping into when I’m going into an organization. I think everyone else would like to know that too. Where are the skeletons in the closet? What are you not telling me. And one of the ways we can get someone to be more honest and forthcoming about the challenges is by accepting some of our challenges and inviting them to share by being transparent, I’ve made these mistakes, I’ve had these failures, that will help others feel more comfortable sharing the things that they ultimately like the high end.

Drew Neisser: It’s so funny. So I was reading the notes from two Huddles we had in April on managing up and sideways. One of the commonalities has shocked me is how many sub-optimal non stellar CEOs are out there. And one of them said in the interview process, it’s all with the CEO, it’s all sunshine and rainbows. And then you get in there and find out this is Negative Nelly, and you’ve got a real problem. I’ll show you a little bit about what I got going. Honesty begets honesty, there seems to be a fine line here, though, in that you can’t diss your previous employer, right?

Jacob Warwick: I think you can get away with it carefully depending on the context. I don’t think it’s good form to specifically blast someone else unless you’re sharing your mistakes as well with it, you might say like, “Hey, we had a disagreement and strategy.” And I know, there’s some folks that I’ve talked to on this call where their strategy was actually right, they got fired anyways, you hear two or three years later, somebody made a phone call, “You were right, you should have done that.” It’s too late. You fired me three years ago, right. But you might share, “I had a difference of opinion, we tore apart.” And you might share the outline without necessarily placing blame, to see whether that new future CEO, or whoever it is you’re speaking with, agrees with your decision in that context as well, you might test the waters ahead of time. So as an example, I worked for a CEO, who we took some VC money, it was about $2 million, we didn’t have product market fit, we had 2 million and this individual wanted me to spend all of that money on paid advertising, just to get somebody into the product where our average time in product was six to eight seconds, I want you to spend $40-50,000 a month to get that from six to eight seconds to 14 seconds so we can get some learnings for the product. And I basically said “No, that is an absolute waste of money. I do not want to just burn someone else’s money because it’s someone else’s money.” Now, I might ask prior to that conversation, “What are your thoughts on extensively spending in SEM, or search engine marketing?” And see if someone says I think it’s a total waste of money, then you have the green light to maybe say this was our difference of opinion that actually came about this thing. But I already know you agree with me on, it’s really more explaining this scenario, the difference of opinion. And it’s not what you say it’s how you say it. So if you just say, “Yeah we didn’t get along, and I moved on. And they fired me.” Which I don’t think anyone would openly say, it’s not going to go over as well, if you’ve structured it in a way to share your difference of opinion and prove that you’re in the clear, before you move that. So it’s very calculated to get to that, but I don’t think it’s necessarily a don’t go there type thing.

Drew Neisser: What do you think are some of the most common mistakes that CMOs make in interviews?

Jacob Warwick: What I’ve seen from a lot of folks, they focus a lot on themselves, their background, their skills on what they’ve accomplished, and less on winning over the other person. And I think I’m a little guilty of perpetuating this myself. My very first blog articles, like, here’s how you answer that, tell me about yourself. You’re just trying to answer this since very self serving, this is how my career’s work. This is how it’s gotten this is that like you practice, polishing, like, here’s the context, here’s the actions I took, here’s the result, here’s the resume, it’s very self serving. Ultimately, it doesn’t matter how good you’ve been in the past, only thing that matters is can you perform in the future. So you have to build that future alignment, the only way to do that is to concentrate on the other person’s needs more so than your own. And more so than what you’ve perfectly polished or accepted. And you could polish 20, 30, 40 stories, and only a handful are going to be relevant to the context and the only way you’re gonna know which ones are relevant or by asking the questions. So as an example, Drew, I need to get you over. I don’t need to tell you everything about myself and impress you. I need to understand what you’re looking for and understand whether or not I can help you or not. So there’s a big mistake in that we often focus too much on how do I tell my past it’s such a perfect way that people understand it with clarity. And I would rather understand how to direct the conversation to understand the future needs and if there’s alignment. There’s just a slight mental shift on like, how do we push this conversation forward and not focus on me or the past?

Drew Neisser: What I was thinking about as you were talking, it’s funny because in Huddles last month when we were talking about challenges related to pipeline, one of the moments epiphany in it as there’s a lot of things they call it sales enablement or they call it buyer enablement. And where we ended up as we call this value enablement. Like, how do you just make sure that you’re doing something of value at every step of the way, so that this value enablement, right, you’re trying to help the CEO see their way or whoever it is, to a future state that you can contribute to. And you’re not going to do that by saying, “At my last job, I did these five things.”

Jacob Warwick: Yeah, you kind of brought on a tangent here. And that is us marketers loving our buzzwords, like sales enablement, buyer enablement. And a lot of times, I’ll see not just CMOs, but folks in general will get hung up on the terminology of what something’s called. B2B SaaS expert with enterprise, yada, yada, yada, you’ll see folks that have 15 years of experience for something that’s only been around for three or four years, which is very interesting, suddenly, everyone’s an AI expert. And so the terminology is always changing, we need to build the breadcrumbs on why it’s relevant. And so you might say, the activities that I was doing in the past, let’s say you’re a head of marketing, and you’re applying for a VP of Product Marketing position. Now, head of marketing, product marketing, two different concepts, all general marketing product arc is very specific and market focused, whatever, you might draw the breadcrumbs out, well, my title was head of marketing, a lot of my duties, were focusing on go-to-market and outline what may be today called a product marketing role. Or as a CMO, let’s say we’re only a CMO of a small team and now you’re interviewing for a CMO of a larger team, you’re gonna have to draw the breadcrumbs on how you can make that connection at the larger level. So while it appeared, we had a small team here, but I actually I also supported the sales team in this effort and the product team in this effort. And ultimately, the org looked like this, and you’re drawing the breadcrumb conclusions on why those things are actually similar. Even if titles or buzzwords are off.

Drew Neisser: We talked about the mistakes of just talking too much about yourself and your past experience. You had used this expression, “Walking the fine line between assertive and arrogant.” There’s a certain confidence that you need to bring to the interview. And that’s through the stories and through your accomplishments and through your questions. But the arrogance part, I guess is the other side of it. “Oh, yeah, I can do this in my sleep.” Talk a little bit about that fine line.

Jacob Warwick: The arrogance was my shit doesn’t stink type of approach, which often I’m very sensitive to this, because I come across as very arrogant all the time. So this may not be the best advice coming from me. I’ve struggled with ego and arrogance a lot in my life. I think the assertiveness comes from being fearless to ask the questions that are necessary. So when you ask me a question, like, tell me about yourself, I actually wrote an article, I think that’s a relatively stupid question. Because it’s not direct enough. Like I want you to be more specific, right? Like, hey, we’re gonna meet. Cool, what are we meeting about? When you’re asked general questions, or you don’t have enough context, or you don’t know how to confidently answer instead of feeling scared, assertively asked the types of questions that are necessary in assert yourself into that and show your leadership and take ownership of that interview. So sometimes you’re working with an HR or maybe a recruiter or Headhunter that doesn’t know the marketing function, or the entire org as well as you do, I would hope not your CMO, they’re a recruiter, as an example. You should feel confident saying, “Can you correct me if I’m wrong?” Like that is an assertive question, that’s not arrogant question to ask. You’re saying, “It sounds like you need someone very adept that go-to-market who can build a team from five to 10 to do this to this. Is there anything that I’m missing?” If somebody said, “Hey, what’s your experience with this growth stage?” Oh, “I’ve done this. I’ve done that. I did that back at Cisco. I did this. I did that.” Cool. Rather than saying all this crap that you did in the past, you say, “It sounds like this is what you need. Is there anything that I’m missing?” I’ll share a couple stories where I’ve tackled this back at Cisco, we had some challenges with this back in IBM, whatever it may be. Now, there’s a couple things, where would you like to say concentrate our focus, because if we cover all these topics, it’d be a couple hours. And one of the things that we could do here is we can control time and keep interest going. Because ultimately, the point of the interview is to get into that phone call, we need to keep the process moving forward. So if we allude to the fact that we know all of these extra things, which we can only do by asserting ourselves in the conversation and showing at least the table of contents of knowledge that you can uncover by continuing to talk to me, and we can say, “Look, we can go into go-to-market, man, we could be doing that for four or five hours across the org. What might be best is, let’s get a roundtable discussion together. Let’s loop in John, the CEO and Kathy, the Chief Operating Officer and we’ll all get together. I’ll do a presentation.” Like you’re asserting, “I’ll do a 30/60/90.” Whatever you’re saying,  these things will happen. “And I’m available on Friday to do that.” Like you are controlling the next steps and asserting yourself of what the next steps of the process could be rather than “Yeah, I’ve done that. Do you care? Does it align here?” So it’s a slight nuance, I think arrogance is talking a lot about yourself, assertiveness is concentrating on them and walking through the steps and the bread crumbs for them. I also call this eliminating the friction of what the next steps may be. So as a recruiter, you might not like I think you’re going to talk to the CEO, I don’t know, you might talk to this person next. And you might say, what I found in the past is that when I get the Chief Financial Officer, the CEO, and one of the board members in the same room, sparks fly. So we should organize that meeting. I’m available on Friday or Tuesday that eliminates the back and forth availability question and you can eliminate some friction, and you’re also assuring yourself, this is when the next conversation is going to happen. And that’s being assertive. And they might say, “Hey, we’re not ready to talk to you again.” At least you know, where you stand. Because you’ve asserted what the next steps could be. They said, “Hey, we’re not ready for that.” I didn’t do so good in that interview. Instead of just twiddling your thumbs and getting ghosted.

Drew Neisser: And as you’re talking, I’m thinking, Oh, my God, I would need to practice this at practice, because it’s new skill set. I couldn’t help but hear you mentioned 30/60/90. And one of the contentious issues among the folks on our transition team is that potential employers ask for free marketing advice. And some do it in a very nefarious way. Like they have no intention, and they just go for it. But on other occasions, the requested thinking can help the candidate think through if they want the job to get to know the company better. How do you avoid giving, quote, free marketing advice, but also, at the same time help you get the job?

Jacob Warwick: Yes. So I’m going to be more controversial than this. And is that if somebody is going to ask you, obviously contextually is important. If it’s a very small company, and those things that are obviously abusing you, it’s obvious abuse. A lot of CMOs make more than $500,000 a year, or even greater, right, I know several that makes several million a year. If somebody asked you to put together a portfolio and it takes you 10 hours, I honestly don’t care, you make enough money to buck up and do the work. Or you say, “Man, I’m really not sold on this company.” Well, you probably don’t have alignment, you don’t need to go through and go ahead and back out and do your thing. Don’t take it out on them and kind of give the employer the benefit of the doubt there. You know how much your time is worth and whether or not you want to put the effort in to make that half a million a year. Hey, that’s on you. I know folks that are getting started in their career that would do anything possible just to have a shot in the room that you’re turning down at that. So it’s kind of a reminder, that is a competitive market out there. And if you want to earn top dollars, you have to perform with that, which is probably not the answer a lot of people like to hear. And the other thing is that a 30/60/90, to me is starting to become a red flag. I don’t think it’s important that you plan out your first 30/60/90 days, it’s the timeframe that I’m worried about. Like why are we worried about only three months of my CMO career here? Is that because that’s a third of my tenure at your company. And it’s really important that I get off the ground, right? Because what happened to the good old days where people would work at a company for five or eight or 10 or 20 years. When you talk to really wealthy folks, and they’re planning out their investments and things, you can tell how successful someone is by the magnitudes of time that they talk about. And I know there’s some investment marketers in here too, so they probably recognize as well. But if someone’s saying, “Yeah, in the next couple of months, I’m gonna be doing this and that. Short timeframe, very short, when somebody is planning on investments that are 8-10 years down the line, I’m going to buy this or renovate it for four or five years, it’s going to make some money in 10 years, they’re playing big time league. When a company is like, yeah, what are we going to do in the first 30 days, I don’t know, I’m going to talk to people on a team and get up to speed. I don’t know anything yet. I don’t know the resources, I don’t have the context, I don’t know the industry, maybe you do know the industry really well. But everything is a little bit more unique. So if they’re expecting big milestone results in 30/60/90, they’re seeing marketing as a transactional cost, like $1 in a bucket and $1.20 back ideally. A lot of marketing is an investment that takes time, advertising might give you $1 in and $1.50 back for some amount of time. But marketing is going to take substantial investment, you’re building brand, you’re developing customer awareness, whatever it may be. Learning the sales team, changing the messaging, it’s a lot of work. And when someone says, “What’s going to happen in 30 days?” To me, it can be a red flag that they don’t necessarily understand marketing in the context that you do, which is fair, you’re the marketing leader, but it may offer an invitation for you to prep. “Yeah, I’m interested in what the first 90 days looks like. But I’m also interested in what 12 months looks like and 24. So let’s extend this out because I plan on being here for a while.”

Drew Neisser: And so the issue is not the free marketing advice, the issue is 30/60/90. And I think that’s a really important point. Because if you want to be there a while and you want to get to know and I tell the story in transition teams Huddle of a Huddlers who actually used the request for a plan to say, “I’m happy to put together a plan but I need to talk to these four executives.” And that process enabled this individual to hit the ground running the plan was actually the plan that they ended up using. And it was a great way for them to sort of qualify the company and take control, as you say. But I think that’s the key there is, they were very interested in the job that only confirmed the interest, they got a chance there was some give and take in this process.

Jacob Warwick: And the thing is, they took it seriously Drew, they said, “In order for me to do a good job, I’m gonna need to talk to these people.” Not, “Oh, this is gonna be a lot of work, let me back out because they’re getting free advice.” So they wanted it and they went for it. So let’s say somebody gives you a 30/60/90, we want it on Thursday, and today’s Wednesday. That happens all the time, they want to speed up the process, especially at startups. You can say, “Well, do you want it to be generic? Or do you want it to be really good? Do you want something that’s going to be total bullshit? Or do you want something that’s going to be very tactical, and something that we can really move on?” And of course, it wasn’t I well, I don’t want the ultimate answer, like, give me some real estate Great, that’s gonna take me about 10 days, I’m gonna need to interview these folks. And that way, we can make it really valuable in every step of the way. “Well, I’m talking to your Operating Officer, I’m talking to your sales leader, whatever it is, I’ll be presenting ideas and providing value along the way and organizing that into a deck to present with you.” That is being assertive.

Drew Neisser: That last sentence is one that I would—if I were interviewing for a job—I would want to memorize, it wouldn’t flow right out of my tongue. It’s been a long time since I had to interview for a job. So obviously, I’m out of practice. But that is a great way of framing it. One of the things about interview processes is that you can end up talking to a lot of people, you can talk to a recruiter, you can talk to CEOs, and there’s often misalignment between those two, do you have any thoughts on the differences? How can you make sure that they’re aligned so you’re not wasting time?

Jacob Warwick: I guess some of the psychological things that we do here is, first of all, you’re working the individual that you’re talking to, not just yourself and your past story or the company necessarily. You want to work with empathy for the person on the other end of the line. So if you’re talking with a recruiter, or let’s say a sorcerer, very early stage, I might be assertive. “Hey, I imagine you’re talking to several CMOs, can you share with me the checklist of what you’re looking to move forward to the CEO?” What’s better is knowing the CEOs name, knowing everyone else’s names and inserting those names consistently to show that you understand their ecosystem. As an example say,  “Hey, what are some of the boxes that you need to check here, I’m happy to share, let’s have a great time in this conversation.” You’re working that person, you’re not expecting them to be a marketing expert. You wanna know what’s going to make you look good to hand me off to the other person. It’s not what you say. It’s how you say it. As you go through. I call this “running the gauntlet” of different people in the organization. You might say, I’ll use Kathy and John as an example, again, Kathy is the CFO or COO and John is the CEO in this context. You might say, “Hey, John, I was having a conversation with Kathy. And we were exploring this particular go-to-market. And it sounds a little different than what you expected here. Now want to make sure we’re in alignment, because there’s good in this, and there’s good in that whatever.” You don’t have to be totally kissing ass here. But you’re wanting to explain like, “Kathy and I were exploring this path. And it sounds like that might not be an area you’re interested in. How can we best move forward in a different way?” It’s not, I heard something different from Kathy and not mentioning it, we have to communicate those things. But we’re not going to throw Cathy under the bus. And I think the other thing to recognize is when you’re on the outside, it doesn’t matter if you’re talking to somebody. I heard this context the other day, a lot of C-suite folks get frustrated when they have to interview with folks that are going to be their subordinates. Because how are they gonna know a good leader when they see one. They focus on well, I’ve done all these things, you should respect me for that. Again, it’s about what is that person looking for? It’s asking them, “What are the best marketing opportunities that you see for the company? You’re the expert on this company, I’m coming in as an outsider, what do you see you’ve been here for two years, you’ve been in the weeds, like, share your secrets with me.” And then we say things like, “As we partner together, we’ll go talk to Kathy and John. And we’ll get this strategy move forward. And we’ll do that together.” Now we’re being empathetic to everyone’s needs. And the key here, too, is using the names of other people will help you be more part of the tribe. When we work with the CEO and the board, you’re saying. “So John, and I are having a conversation the other day, and we were talking with Kathy.” We’re familiar, we’re using name association, and we’re talking with others. “Sounds like there’s a difference of opinion here. Now, let’s iron this out.” Still solution-oriented. It’s not necessarily blowing smoke. You’re not hiding from the misalignment. You’re calling it up, but you’re not calling it out like somebody’s stupid for not knowing. You also mentioned that you’re out of practice when it came to interviewing. I think that the pressure that folks put on themselves in an interview environment is one of the big challenges that we have is that you got to get it all straight. In interview mode, I got put on this something. It’s a facade. Ultimately, it’s a little bit more perked up and a little bit more attentive than you typically are which just makes you nervous, you have to perform a certain way, you have to think about all these things. And when you truly have executive presence, you’re definitely more relaxed and you’re open and you take up space. And look, we could just naturally shoot the shit and have a conversation, because you’re comfortable. And this is an environment that you don’t have to practice for so much. It’s just a conversation. When you change yourself and you stress yourself out and you try to be someone that you’re not, one you get misalignment, because you’re showing a character that you’re not actually every day, that pressure often puts you in a subservient role to whoever you’re talking to, because you have a need to impress and a need to fit in and need to move forward. Now, I don’t know about all the other C-suite executives here, but subservient and executive is not a good mixture. So we’re looking for casual like we’re peers, even when you’re talking to subordinates, we’re appears when you’re talking to the sourcer recruiter, we’re just peers, we’re solving problems together. It’s not anything you have to stress yourself out over and perform in some archaic interview way where you’re starting all your clothes, and straightening the tie doesn’t have to be so strict.

Drew Neisser: I get the being comfortable and being yourself and trying to bond with the individual. I do think that there are certain expressions or ways of framing a conversation that may not be initially natural, that could become natural with practice. That’s all I’m saying. I’m not saying be somebody that you’re not, if you’re used to, for example, telling your story in a chronological way, and suddenly you need to change it and do it in a different way that might take some practice, a little bit of rehearsing probably wouldn’t be a bad idea.

Jacob Warwick: So one last piece there is it’s okay to narrate that you’re not an expert. So you might say, I haven’t interviewed in man a decade, let’s say you’re coming from a long tenure, I haven’t interviewed in like a decade, you’ll have to forgive me, I might be a bit rusty. It lets the monkey off your back, you’ve at least address this possible insecurity that you have about not being as polished. So you’re letting people know, it could also show you a really loyalty your company were there for 10 years, you didn’t need to do any candidate interviews, where you’re always recruited out of roles and people pulled you or somebody, because that happens in our careers, people pull us to the next job. So you haven’t had to be practiced with this. “So thanks for bearing with me, I might be a little rusty. And I’m still working through I think what some of my key learnings here are, and these are the areas I think are most applicable, maybe you can support me if I’m wrong.” How you organize, narrating your thoughts and asking the questions and building out the breadcrumbs. More important than being perfect. And dialed in. “I did this in college, and then I got my MBA, then I went back for a PhD in communications, because that makes me a great marketer, great the AI world.” Whatever it may be, you don’t have to spin all that stuff in that particular way.

Drew Neisser: Large number of Huddlers are women, do they face different challenges in interviews?

Jacob Warwick: Absolutely. We are different in a lot of ways. What’s interesting is I’ve gotten a lot of pushback, particularly on the aggression versus assertive piece, because I didn’t used to call it being assertive. And I actually called it aggressive until a female executive called me and said, these are great strategies for men who won’t work for women will look like bitches. And women have to balance that line all the time. And I push back. I’m not trying to be aggressive or bitchy. It’s the difference between that and being assertive. And what’s interesting is most of my career has been as English as a Second Language minorities and women, primarily, I don’t actually work with a lot of men. And what I found is a lot of men are very confident, but feel like they need support in a lot of ways. And sometimes they just kind of naturally fall into that. What I learned on the assertiveness sides, I’ve learned most of my assertive traits from women specifically. And that’s because I found that they often will study ways to master communication in order to feel comfortable in the boardroom in ways that they’ve been, I’m unqualified to say this, but maybe oppressed in the past. I don’t know if that’s the right terminology, but ways that women have had to work a little bit harder than someone like myself. And what I’ve seen is some women that have been masterful in their communication and how they say things and how they pull people along. And yes, we’ve dealt with the both the men and the women that are overly aggressive and total assholes and man I would never want to work for that person. So that’s not gender specific. But I have learned a lot from how it’s almost had to be a little bit more delicate. It’s not like locker room talk. And in all of the boardrooms, especially in Silicon Valley, and especially in more of the tech focus centers are going to be a little bit different boardrooms than say boardroom in Texas. There’s always a different environment that you have to play with and different challenges across the board. It’s very difficult to have like a generalization of what works and doesn’t work there.

Drew Neisser: Perfect. So a lot of folks in the transition team lament that they got down to the finals or were just to CMOs but then they didn’t know who their competitor was, but then they find out they didn’t get the opportunity. And then they ask why and then they get some legally safe answer that doesn’t really give them any information that they could use next time. Is there any way to get information that would help you increase your odds of getting the job that you want next time?

Jacob Warwick: Yes. So this is going to potentially piss people off. But if you don’t know where you stand prior to the decision being made, that’s your fault. You need to address these things sooner, and you need to address your competition sooner, in differentiate yourself from the competition better ahead of time, after the fact, basically useless. Legally you’re trapped. Some of you who are working in companies where you’re absolutely legally trapped, or in industries where you just can’t touch it. You might get away with it at some startups, where somebody like kind of has a heart to heart with you if you really ask or if, but you should know where you stand ahead of time. And so one of the concepts that I help some clients with is how to build a wedge between you and your competition, and how to differentiate yourself from the competition. So as an example, let’s say you use the concept like, “Hey, I hired somebody local, instead of somebody across the pond or something.” Let’s just say you’re in Europe, you should have addressed that concept way sooner, you should address how people are different. Let me give you an example. Look, you’re hiring a CMO for the first time. I want to understand why do you want someone so senior? Have you considered hiring Maybe someone with 5-10 years less experience, maybe two of those folks and building out a team There?” Hear their answer. “Oh we don’t want that we want somebody senior.” Cool. I’m senior, tick that box. “Have you thought about hiring someone local, someone in office every day, so they can share the executive presence what are some of the pros and cons of that for you?” They might tell you an answer. “Now, have you thought about going to an agency? Why not just offload all this to an agency, have that Agency report into you, and save some money on a senior hire like me?” So this is how you could wedge out your comp expectations too like you’re building the allure that you’re expensive. “Let me challenge you. Why would you work with somebody with my level of expertise, versus three or four junior folks or a vendor or this or so on remote or this whatever all the different options may be?” And you’re quite literally negotiating against yourself. They’re affirming, I want someone like you because of this, I want someone like you. So now they have to be consistent with their desires. And what they’re desiring is, by definition, in the way that you’ve outlined the question, what you’ve described is yourself. So I’m saying, this is arrogant. By the way, this is sarcastically arrogant, “Why would you hire somebody expensive in senior and strategic in whatever it is your trades are? Have you considered a vendor? Have you considered someone more junior?” And they’re talking themselves out of your competition along the way. Then if you don’t get the job, you at least know, “Hey, we chose to go with somebody that was local, because that was a sticking point for us.” And you knew that ahead of time, which could become a negotiation key a little bit later. I call that driving a wedge, give them every option, talk about all of your competition, talk to your competition up and have them affirm that you’re the answer. And as they’re affirming their list, you’re like, there’s a story, I can tell there’s something I can drive a little deeper, there’s something I can confirm, be consistent with. So you know exactly what their intentions are and you’re the only candidate that once you’ve eliminated all their other options, who has negotiation power at that point. They have no other options, they’ve verbally committed to you every step of the way, you know exactly what you need to do to win that deal.

Drew Neisser: We probably could just keep going and keep going on interviewing, but we did promise that there would be some conversations about negotiation. And it feels like you and I talked about that the negotiation begins before the interview. And then we just had a question about how do you handle the questio, “What are your compensation requirements?” So let’s just try to thread those things in terms of negotiations together.

Jacob Warwick: Yeah, this is the fun part. Because if there’s one takeaway that anyone’s gonna get from this will make you several 100,000, if not millions more in your career by getting these pieces, right. So one is, you’re negotiating before you have the first conversation in a couple of ways. And that is, people will consider there’s a perception about Chief Marketing Officers. There’s a perception about Chief Marketing Officers at startups at midsize at larger companies. There’s a perception about Chief Marketing Officers based off of the compensation benchmarks what recruiters think what people say about you, your network, all of these things, play to your perception. So if you’re a CMO at a series A, the perception might be this person makes maybe 200 grand, they’re very hands on and tactical. That will influence your negotiation, it will influence the direction of where you’re going, it’ll influence the first offer. So this means we need to be exceptionally mindful about the positions that we choose how we publicize them. The other piece is that nobody knows your career like you do. So you don’t necessarily have to broadcast every single damn thing that you do on LinkedIn, which is contrarian to what a lot of LinkedIn experts will tell you, share to the world. Well, a lot of things are difficult to walk back. Hey, I just got this new job didn’t work out three months later. Who looks like the asshole is it the company or is it you for only making it three months. Be mindful of what you say because what you say on LinkedIn what you have randomized the companies, the company wears perception for you, it influences how much money you make, how attractive you are to recruiters. How many folks have been like, Oh, we’re just gonna hire folks for Meta. If you worked at Meta, you’ve been validated by the world, therefore, you are good. Not true, by the way, but that perception helps influence their career forward. Now, the piece that will make you the money is, one understanding how these things interact. But it’s that compensation question, you often get it from the recruiter screen. And sometimes it’s the first question they ask, which is frustrating. Sometimes they butter you up for about 28 minutes. And then as they’re scheduling the follow up, they just link it in real quick to get you to answer but there’s only like a minute left, just to pressure you into that little time block, which can be pretty frustrating. And so on the compensation question, we’re not necessarily deflecting, we don’t want to be deceptive, we don’t want to say we don’t want to answer that, but ultimately, if you’re hearing about the recruiter screen, it’s too damn early to know for sure. How many people have interviewed started with one job description and ended with another when they were done. But the first thing you said was, I want to make $400,000 a year. Now the job suddenly has three or four new teams reporting into it, you’re doing all these other things, hey, the title even dropped because they changed the job, whatever, they change a bunch of things. But you’re committed to that one thing that you said right at the beginning. So like to be a little looser in that context. And see, you may push back and say, look, it’s a bit too early to know for sure I won’t discuss compensation until there’s a written offer on the table. That’s a borderline aggressive way of saying it pushing back. You may say, “Hey, I recognize where you may be asking that right now want to make sure we’re in alignment compensation wise. Now, for me, it’s too early to know for certain what that compensation expectation should be here, can you share a little bit about the range that you’re working with?” So this is turning it back on them to get their numbers to know if it’s worth your time, so that I can share whether or not we should move forward. And you may get some pushback there. If you’re a C-suite executive, you should be pretty used to awkward and challenging conversations. And if you’re getting your ass kicked by a 28 year old sourcer for a job, like we need to reevaluate our career choices, we could push back on them. The other thing is, when you’re in a position of transition, they say that having a job is better than not having a job. And I don’t know if that’s a attractiveness, like somebody’s willing to hire you, therefore, you must be good type of deal, I find that it is pretty emotional, in that when you have a job, you can say no to things, because you’re already getting paid, and you are already paying your bills. And you don’t really need to make a move. Unless the job is absolutely terrible. When you’re in transition, you’re more eager, like, “Hey, I gotta get some money coming in to pay these bills to pay for my kids to do whatever it is you need to do.” And as you are more eager to get something, you lose negotiation power, because you can no longer say no in the same conviction that you could before. And so that will cost you money. I focus on money here because money typically peaks folks interests a bit more than the other things that we can negotiate for. I know we’re rapid fire on negotiation advice here, so bear with me. But being able to push back and not overshare early is very important until you know more information. This is also important that if you’re going from a startup to a midsize, the pay structure is totally different. It also means that when you see there’s a lot of salary transparency laws coming out great, you can see the range, sometimes the range is obnoxious, sometimes it’s not. Sometimes the range is a bit beneath what you’d like. And you don’t think you can break that range. In many cases, that’s bullshit. Rules are meant to be broken. There are alternative ways of getting paid what you can’t negotiate today, you may be able to negotiate for later as well. It’s tricky because you will sound like an asshole if you challenge all authority, which I have done time and time again, usually in a losing context. But when you see a set of rules, like here’s the job description, here’s exactly the range that we’re expecting to pay. Okay, let’s move forward and let’s explore, you can still win more than what they tell you. If you keep the possibility open.

Drew Neisser: Clearly, we’re going to have to have you back. And we’re going to have to do this again and spend more time on negotiation. I still had a ton more questions for you on interviewing, but I need you to provide two do’s and a don’t when it comes to interviewing for a CMO role.

Jacob Warwick: Do focus on the future, not your past. That’s the biggest takeaway always focus on their future and not your past and how you can create that alignment. The other one is the quote you had earlier was do focus on alignment and not being impressive, since you handed that one to me. Don’t share your compensation number until it has a written offer on the table.

Drew Neisser: Awesome. Well, there you have two really important dues and one very significant don’t as I was thinking about, you’re saying you don’t want to be the one to break prices. That’s an old rule of sales negotiation. Don’t be the person to set the bar. After all, they’re hiring you they have numbers in mind, so you can take advantage of it. All right. Thank you Jacob Warwick amazing conversation. 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 To hear more conversations like this one and submit your own questions while we’re live. Join us on the next CMO Huddles Studio. We stream to my LinkedIn profile, that’s Drew Neisser, every other week.

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 our B2B podcast partners Share Your Genius. 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 I’m your host, Drew Neisser. And until next time, keep those Renegade thinking caps on and strong!