Flip the script! Questions Every CMO Should Ask Their Next CEO

You're interviewing them just as they are interviewing you. It's time to flip the script!

You’re not alone. We’ve all worked for a bad CEO at one point or another. You interview with the CEO, they seem great, and yet once you get in there to do the work, suddenly, you feel as if the rug has been ripped out from under you. So then you rack your brain to figure out how in the heck do you avoid this in the future?

Like with any job, you’re interviewing them just as they are interviewing you for fit, skills, strategy, vision, etc. However, when a CEO is on the hunt for a CMO/VPM it’s usually because of one or more things:

• If the role is for a VPM reporting to the CEO, they likely need a babysitter and may/may not really understand the value of marketing

• If it’s for a new CMO role, they usually want to grow the company and figure it’s time to finally invest in marketing

• If it is for a replacement CMO, they are looking for something specific — either fill the person’s shoes who left or bring something else to the table they didn’t have

And of course, there are a lot of other factors to consider such as, if this is a PLG company, if this is a first-time CEO, if this is a first-time founder CEO, does the CEO have any marketing experience at all in their background. All of these things matter. But you should still come to the table with curiosity and questions.

Here’s a list of questions I’ve previously asked, and afterward I perform my due diligence on their answers by speaking to former and current employees. I’m a straight shooter so my questions are more direct, but feel free to massage them to best suit your personality.

1. What problem(s) are you hoping for someone like me to come in and solve? What do you think is broken within Marketing? (or more eloquently put, If I were to come on as VPM/CMO, how could I best help you move this company forward?) It’s important to understand what they think is broken because you’ll need to fix that immediately and it’ll also be part of the criteria for judging your success. Plus, 99% of the time it’s why they are hiring for this role. Something is broken and it’s either people, process, or systems (usually the first two) and they want someone to come in and fix it.

2. What does good marketing look like to you? Can you give me examples of brands that you think do really good marketing? How will you measure success for this role? Let’s face it, good marketing is in the eye of the beholder, however, it’s important to understand how the CEO defines what “good marketing” is so you can meet and exceed those expectations. It also will give you some insight as to whether or not you need to educate them about the impact of certain activities, such as PR/AR or brand, as an example.

3. We all have strengths and weaknesses, if I were to ask your board to tell me the one thing they think you could work on, what would they say? This always gets a “great question” response because it makes them think about how others perceive them and that’s something they probably haven’t thought about in a long time. It also gives you insight into how self-aware they are as a leader.

4. What’s your short and long term vision for the company? This lets you know if they’ve thought beyond the immediate future. Most CEOs have short and long term goals of where they envision the company going now and in the future. Also, a mission statement is not a vision statement. Make sure you are both clear on that.

5. What % of the product is true SaaS? For SaaS companies in particular, there are just way too many of them that are services companies under the hood masked as true SaaS companies.

6. What types of decisions do you expect to be a part of? There is always a level of trust coming into a role. Some CEOs want to give you carte blanche, after all that is why they are hiring for this role. Whereas others want to be included in certain types of decisions. Try to dig in here to find out what those are. For example you could ask, “For example, if I were to change the brand or change pricing, are those items that you would want to be involved with? What about a quote from you for a press release?”

7. What’s the company’s revenue, burn rate and NRR? Are you profitable? Are you cash flow positive? What’s your cash in bank? What’s the total head count? The recruiter or HR person will tell you what the revenue is, but what you really want to know is whether the business is healthy or not. The monthly burn rate (how much they are spending to run the business) and how much cash they have ( a good measure is 24 months of burn), and whether or not customers stay or churn, is extremely important as to whether or not this business is healthy or not. If they don’t want to share, offer to sign an NDA. But any serious marketer would ask these questions in an interview and any legitimate CEO will give it to you. Don’t be afraid to ask the hard ball questions.

8. What was your most recent 409A and is the current exercise price the same as the 409A? What you’re looking for here what is the current valuation. Does it seem aggressive or a reasonable multiple based on what you know about the industry and the business? What’s the number of fully diluted shares? You want to know if you should negotiate for equity or not and how much.

9. How do you view AI in Marketing? Should everything be optimized for AI? Is this something you expect the CMO to drive?
   This gives you insight into how they think AI should be used within Marketing and if they are expecting you to drive the initiative or to partner with other teams. It also gives you insight into how they view the marketing org and how AI will play into organizational development.

There are lots of questions you can ask, being curious and doing your research will help aid the discussion. These are just some questions to get you started.