The Race to Reduce Risk in CMO Recruiting: Highlights from Season 6 of The Get

Welcome to The Get. I'm your host, Erica Seidel. I spend my days recruiting CMOs and VPs of Marketing in B2B SaaS. I'm all about placing the make-money marketing leaders, not the make-it-pretty ones.

This season is the sixth season of The Get. We've been focusing on the race to reduce risk when it comes to a match between a company and a CMO. How can you find out what you need to find out before saying yes so that you can make smart decisions that stick? Whether you're hiring a CMO, or looking to step into the role yourself, you will learn a lot from this season's conversations.

The takeaways range from the practical to the provocative. Today, I'll summarize some key insights. As you listen, make a note of topics that seem particularly compelling so that you can listen to those episodes separately. Let's get started.

We'll look first from the perspective of the CEO or the investor for a company that's hiring a CMO. If this is you, you know that the CMO role is high stakes. Marketing is often central to a company's growth plan. Often, CMO roles are "revenue rescue missions," in the words of my guest, CMO Melissa Sargeant.

The challenge is that marketing is one of the least understood executive functions. This came up in my conversation with Peter Mahoney, Chief Commercial Officer of GoTo. We called his episode What CEOs Fear Most When Hiring CMOs. He discussed how everyone at the C-level thinks they understand marketing, but at the same time fears that they don't understand it.

That's a lot to unpack. Part of it is that CEOs fear that the new CMO won't connect with what the actual problems are to be solved and what their role should be focused on. You could worry about hiring the CMO who focuses too much on flashy campaigns and not enough on delivering measurable results. You could also worry that a marketing leader will overspend in general or fail to adapt to your company's growth stage.

Another worry is just not knowing what you really need. Maybe you've made hiring mistakes before, like hiring a demand generation expert, when what you really needed was someone more T-shaped with more strategic background. One thing's for sure, CMOs don't fail for lack of effort or lack of talent. They fail, when they do, because of lack of clear role design, and they fail because expectations are not aligned, especially for how long things will take.

James Lamberti, who's Head of Go-to-Market for the investment firm Georgian, discussed this on the episode called Top Threats to CMO Success and How CEOs and CMOs Can Tackle Them Together. This is a common issue for technical founders, first-time technical founders, new day, new strategy. It's a reset button on marketing, and I will often try to break through with a technical founder by explaining when you reset your marketing strategy, it's the same thing as if you fully reset your product strategy.

You would never just go into your product team from an R&D perspective and shred the two or three quarter product roadmap because you're putting your entire dev team back to zero. Marketing actually works more like product than it does like sales. The returns on it are two, three, four quarters out. And so that is a huge area where if you don't pull that out of the conversation effectively, that can come back to be really painful because every quarter we're gonna switch strategy and marketing, and then you can never get anywhere.

And eventually you're out the door in four to six quarters. So, how can you de-risk CMO recruiting? First, clarify your needs ahead of time. Co-create the role with candidates, learning as you go.

The best CMOs are also Chief Marketing Education Officers. Ask them to teach you. One of my clients asks candidates things like, how should I think about ABM? And asks for them to educate her.

Next, make sure you have a structured framework to vet candidates, and reduce risk by considering a trial period, like having someone work on a fractional or advisory basis before making a permanent hire. Beyond interviewing, acknowledge that the CMO role is on a different time horizon for producing value than some other functions. Their value is not just this year, but in years two, three, four, and beyond. This means that CMOs have to embrace the duality of being asked to produce both short-term and longer-term value.

Norman Guadagno, former CMO of Mimecast, discussed this in his episode called, What Veteran CMOs Know That First-Timers Don't. Fundamentally, I think the CMO has to embrace the duality of no matter what, or at least most of the time, you're going to be asked to produce something short-term. Just the way business works. And what you have to be able to do is explain, yes, I can do X, Y, Z.

But you also have to be right, clear, upfront. There's a set of other things that are going to take longer. And I want to make sure I lay them out right from the start. And I give you my best estimate on how long this will take.

Oftentimes, and we can't avoid this discussion, it'll be brand. "I want to build a big brand." "Let's make the brand better." Awesome!

We all love that. But it doesn't happen overnight. Everyone knows that, but doesn't know that. You know it intellectually, but every executive, CEOs included, are under pressure from someone else to get results faster, especially in today's climate.

You have to start to think about, there's not one timeline that you want to talk about. You want to talk about the timeline for things that will happen in months and quarters, and the timeline for things that will happen in quarters and years, and how do you balance those? And how do you know that, I understand that it's going to take a while. And this is something I've experienced multiple times in my career.

I have had the discussion with boards, with other executives, where I say, this is the thing we're going to do. We'll talk about brand. We're going to invest in brand building. It's going to take three quarters, four quarters, whatever numbers I put on the board.

And then I also say, we need to have it be sustained investment. If you lose your patience in two quarters and want to pull the investment, we shouldn't do it at all because then it's just wasted investment. That then shows you as a good economic business decision maker. Also, look for CMOs who use collaboration, education, and communication as their not-so-secret weapons.

Tracy Eiler, who's CMO at Open Sesame, discussed this. As marketers, we end ourselves up in businesses where we have to do loads and loads of internal marketing and communicating and not only about what we're going to do, but what we're not and why we made a decision to do thing A versus thing B. In fact, right now we're working on a website redesign and we're using a very much iterative kind of testing approach to decide where we land on fundamental things like our homepage.

And, you know, I'm using that mantra that we are continuously testing because of this constant opinion that we keep getting back. So that for me is a scenario that I think we all should expect that there's going to be lots of opinions about what we should and shouldn't be doing. And we need to be the ones that are going to provide clarity on how we're making decisions and why. Now, let's look at all of this from the perspective of a CMO who is considering joining a company.

If this is you, there are some red flags that you would be wise to be on the lookout for. I discussed this topic in detail with Melissa Sargeant, who is CMO at Lumaverse now, in our episode on Avoiding Red Flags and Decision Making Flaws in CMO Recruiting. One red flag is that the company used to have product market fit, but doesn't anymore. It can also be a red flag if the company is pitching a strategic CMO role, but they really see marketing as a lead factory.

Another thing to look out for is a situation where you won't actually have the resources and authority to succeed. This can sometimes be the case when the head of marketing reports to the CRO, which is a topic we covered in several of the episodes. Another red flag to look out for, that the company won't really be ready for change. That innovation is needed but not wanted, in other words.

Relatedly, it's a red flag if the CEO has overly optimistic expectations of what marketing can achieve in a certain time frame. Obviously, there's a lot to consider before you say yes to a role. Part of evaluating a position entails tuning into your own appetite for risk. Realize that your perception of risk changes as you evolve in your career.

I talked with Norman Guadagno about this. Norman has led marketing many times, including most recently at Mimecast. We talked about what we called an arc of caution in career progression. What that means, as a marketing leader, you could go through stages with your relationship with risk.

Early on in your career, you could be very open minded and gung ho to take on big challenges, even with risk. You just don't recognize the risk in a situation. Then, as you get more marketing leadership experience, you're increasingly able to recognize risky situations. Over time, you'll be able to identify more warts in a situation, so your risk profile peaks.

Then, you may right size your risk if you diversify your career by contributing to different boards, for instance, or if you take on a non-marketing role. So think about where you are on your arc of caution. Okay, we've looked at the risks that CEOs and investors perceive and how to mitigate those. And we've looked at the risks that CMO candidates can notice.

Now, let's finish by looking at ways that you as a CMO candidate can mitigate risk before saying yes to a role. First, look inward when you're at the start of a career transition. What are your non negotiables? Maybe you need to report to a CEO and won't consider reporting to a CRO.

Maybe you need clear evidence of product market fit. Next, define what my guest James Lamberti calls your ideal CEO profile and how to add value to that person. Also, do your due diligence on a company's culture, leadership team, and strategic priorities. The best CMOs have frameworks for doing this, like Tracy Eiler, who has a rapid pressure testing playbook that we talked about.

You'll come up with your own. Analyze the growth metrics. Consider calling up people who have worked for the CEO before. Ask for a product demo to evaluate the company's go-to-market maturity.

The first episode this season was called Everything a Good SaaS CMO Should Find Out Before Saying Yes to a Job. I interviewed Andrea Kayal, CRO at HelpScout and a former CMO. Andrea talked about some of the key things she looks for. Here's a clip: If the gross retention is suffering below 90%, that is a problem that the product team needs to solve.

And the VCs and the CEO, very apprehensive to spend more at the top of the funnel generating more leads and more pipeline and more revenue, if they know it's leaking out the bottom. So that's definitely the question I would ask, that's far and away the most important. The second thing to look at, if I were a marketing leader joining an organization is probably the close rate percentage. Because the worse the sales team is at closing deals, the harder the job is for the marketing leaders because you are covering what their quotas are.

So if their close rate is 25%, then you need to be covering, you know, you need 4x the pipeline to cover that. If they close at 20%, just five points less, you need five times the pipeline to cover that. And what happens is, as that close rate changes, the budget you need to support that organization also needs to increase. And sometimes that's not clear to the company that it's not, it's nothing that I can do to solve for this.

Every time the close rate goes down, the budget for the marketing team needs to go up. So, those are probably I think the top two that I would be digging into. Another good perspective on what to ask when doing your due diligence comes from Melissa Sargeant, multi-time CMO now running marketing for Lumaverse. She shared a couple of key questions she uses to suss out organizational dynamics.

So the areas I really like to dig deep into are the dynamics around how that executive team works together. I will usually start at a higher level and ask about how does strategy get developed here? And often people will say something like, we do OKRs, or we do the V2MOM framework. Great.

I love frameworks. How do you get there? What happens before that comes on paper? Oh, we go on an offsite.

Fantastic. What does that offsite look like? Do you, Ms. CEO, come to that meeting with documentation that you've put together in terms of your goals and here's how you see the strategy?

Do you have each of your executive team members come prepared with a presentation or a talk track on what they see the strategy is? How does that happen? It's very telling about the dynamics of that organization because what I've seen is some very top-down structures where the CEO, or maybe it's a founder CEO, very common, certainly in my space, is the visionary in the company and they're the person that's looking around corners. So they have a very clear view of what they think that strategy should be.

Or perhaps it's a more mature organization and all the key stakeholders, all the key executives come with what they think. They've done their research and they've gotten their feedback from customers and they come to the table with that. How that process happens and the discussions that happen around it is incredible insight on how that team works together on a daily basis and what you can expect to see in your executive team meetings. Because in those meetings, my view is that everyone should be talking.

And some organizations, if you see or if you hear, it seems like there's one person who talks the most and others are just listening and maybe asking a question. That's something you want to understand a bit more about because if everybody really has a strategic seat at that table, how that process happens is really critical. The part two of that that I will ask them is, how do you disagree? You get lots of different responses to that.

In a healthy working environment, there is a level of disagreement that's necessary to move the company forward. It can be done in a respectful and professional way, but it should be a red flag for candidates if they see those interactions, and if you feel like you get into these spirited discussions and then you go away from that meeting, and if you have to spend the next two weeks repairing your relationship with your colleagues, it's probably not a healthy organization that celebrates and wants those diverse voices at the table.

Next, treat the interview process as a two way dialogue. Sometimes, candidates don't realize that they can help the recruiter and the CEO to shape the search and the outcome. By coming prepared with specific frameworks and questions, you can position yourself as a strategic partner rather than a transactional hire. Beyond simply positioning yourself for the role, the recruiting period is a good time for starting to align expectations the way you will do when you are in the seat.

James Lamberti, the veteran CMO who's currently at Georgian, shared how he has collaborated with CEOs to jointly figure out a fit. I always try to, in the early stages of the interview process, start to probe the CEO and be like, for example, starting with the ICP definition, who are you selling to? Please tell me all you can about the specifics of who you're selling to, and what I'm trying to understand is how well defined is the ICP? And does this CEO founder truly understand how important it is to have a specific, quantifiable description of the ICP, and how focused and quantifiable is it?

The more clear that is as a marketer, of course, frankly, the easier it is for you to add value. 'Cause if you're coming into a company that's like I know my sales addressable market in the next twelve to twenty-four months, it's $350 million. It's in these geographies. It's this type of persona.

It's this pain point that I'm solving for. These technologies are present as a clue or signal from an intent perspective. All those details are so valuable for you because you can now be laser focused on doing what you do as a marketer, which is drawing a circle around that market from how you do your targeting, your demand gen, your brand building, your messaging, your event selection, all of that. And throughout the process, realized that it often takes a village to make a smart career decision.

I talked about this with Tracy Eiler, CMO at Open Sesame. Our session is called CMO Secrets to Maximize Recruiter and Network Relationships. Tracy shares her roadmap for staying in touch with her network in an almost programmatic way. She talks about the importance of a personal board of advisors.

People that you can share job leads with, swap ideas with, get advice from, etc. From my standpoint, one of the best lines of questioning I get from candidates is simply, how do I line up with the spec? What are the concerns that the company has about my candidacy? Now, once you're in the role, your risk mitigation strategy does not end.

It continues. How can you increase the chances of success? First, realize that your job is not just marketing. Peter Mahoney, Chief Commercial Officer at GoTo, makes the point that fifty percent of the CMO role has nothing to do with marketing.

The first time you're a CMO, you may not realize this, that only half of your job is marketing. The other half is being part of the executive team and leading the business, and that requires a different set of skills. One thing Peter recommends, if you need to, call up a friend in finance and have them walk you through the P&L. They'll be happy to do it.

Next, realize that change may take longer than you think it will take, depending on a company's appetite for it. First-time CMOs may be overly optimistic about how long it takes to implement change, so they may fall into the trap of over promising and under delivering. Beware that, and manage up around expectations and timeframes for results. For instance, if you're doing a big rebrand, tread carefully, communicate thoroughly, and set clear expectations of how long it'll take.

Maybe you tell your CEO that since brand building is a longer term thing, it's natural for them to start feeling antsy in a few months into the project. Get to know the talent on your team, both the people who are in their seats already, and people who are interviewing with you. Peter Mahoney shared a good perspective about how to assess talent. When I just took over this go-to-market organization, there was a lot of questions about, well, what's he going to be like?

How is he going to be as a leader? And I spent a lot of time telling people that I like as a leader myself, I like to start by understanding. I like to dive into a lot of detail to understand what's going on. So I'm going to ask a lot of questions.

I'm going to really try to understand, maybe peel back the onion, push on you a little bit to really understand what's going on within your particular domain. And then I'm going to back off. Ideally, I want to get to the point where I give you a set of guardrails, give you a goal, say this is what I want you to achieve for your particular area, give you some guardrails, and those guardrails are things like these are the behaviors that we accept, and this is the way that we operate as a company, this is how you need to communicate, etc.

But it's really important to be able to have that beginning part, be able to really dive down and understand the specific domain, and that's one of the things that I find some of the most effective executives can do. Even if they're not an engineering leader, as an example, should absolutely be able to ask provocative questions that are at least logical questions. It doesn't have to be about a specific line of code. You should be able to understand and question people to the level that you understand what their level of understanding is, how confident they are, and whether they really have a plan to achieve what they're saying they're trying to achieve.

Next, in a new role, think about how you can build a flywheel of credibility. Gary Survis from Insight Partners talked with me about this. We called our episode, Building Your Flywheel of Credibility: A Playbook for New CMOs in PE-backed Companies. Take your time initially to build an assessment of the org.

Identify and surface problems rather than sweep them under the rug. In other words, diagnose, don't delude. Be able to make swift organization decisions. As Gary says, if you're not successful because the people below you are not strong, you have no one to blame but yourself for not making the changes you know you need to make.

Gary also encourages new CMOs to have a perspective on AI, including how to organize their teams and define roles differently for AI supported marketing. I'm encouraging CMOs today to think about whether they want to create a BG or an AG organization, Before Generative or After Generative organization. If you choose to do the BG organization, recognize that the responsibilities are going to change, the roles are going to change. Or, are you going to try to start moving your organization to the way technology is going to change the structure?

For that reason, I encourage them to do a little more forward thinking about what people's roles are really going to be, where you're going to need. Do you need five creative people? Do you need as many writers? Do you need more editors?

What do you need based on how this technology is moving? You should have a point of view. Taking a step back here. A successful career, in my view, comes from three things - talent, good luck, and good decision making.

Let's assume you're talented, and let's assume luck is out of your hands. The lever that you're left with is your decision making. In the episode I did with Melissa Sargeant, who's now leading marketing at Lumaverse, we talked about the flaws in decision making that can get in the way when hiring or getting hired. For instance, trusting someone else's due diligence without doing your own.

Thinking that this situation is so much like another, so the same playbook you used then will work now. Or the same person who did this job in another company will succeed at your company. Another flaw? Falling in love with the company that someone worked at, rather than focusing on how they approach their role and their work style.

Remember, sometimes a company is successful because of someone's contribution, and sometimes it's successful despite their contribution. This all sounds very analytical. The fact remains, there's only so much de-risking you can do with a hiring decision before taking a leap. That's why your gut matters, too.

In my episode with Melissa, she said something that stuck with me. "Your gut is your truth." So if you feel a red flag, be curious and investigate it more. Learn to recognize and interrogate your gut.

Translate for it because it doesn't speak English. I hope these insights from our guests have given you actionable ideas for your next big CMO recruiting decision. Thanks for listening to The Get. I'm your host, Erica Seidel.

The Get is here to drive smart decisions around recruiting and leadership in B2B SaaS marketing. We explore the trends, tribulations, and triumphs of today's top marketing leaders in B2B SaaS. If you liked this episode, please share it. For more about The Get, visit TheGetPodcast.

com. To learn more about my executive search practice, which focuses on recruiting the make-money marketing leaders rather than the make-it-pretty-ones, follow me on LinkedIn or visit TheConnectiveGood.com. The Get is produced by Evo Terra and the team at Simpler Media Productions.