Deb Wolf has served as CMO at Dataminr, Lookout, and BetterUp, and was Workday’s first marketing hire, helping build the function through IPO. As part of the 53 Stations Wayfinder network, a curated community of executives, operators, and industry experts supporting founders directly, Deb offers hard-won perspective on early GTM decisions, hiring strategy, and making AI adoption stick inside a team.

I’ve led marketing at companies from their earliest stages all the way through IPO. Along the way, I’ve watched smart founders make the same fundamental (and sometimes expensive) mistakes: hiring in the wrong order, staffing for the wrong stage, entering into a new region without a fully-baked company plan, and forgetting that every new technology—even something in a category of its own, like AI—requires a change management strategy. This is the advice I’d give founders today, after 3 decades in the field.

Get your narrative right before you hire for demand generation.

The single most common mistake I see is founders hiring for demand generation before they really understand the market, recognize the customer pain points, and build a compelling narrative about how they solve a customer’s problem. Sure, they know their product and are innovating, but have they really solved a market problem worth the investment they are looking for?

Pre-Series A, you need someone who can do the hard foundational work: messaging, competitive positioning, pricing strategy. This is someone who can translate what your product does into why it matters to that specific buyer. 

If you hire a demand gen lead before that narrative is solid, you are spending money to amplify confusion. Wait. Do the positioning work first. When you start approaching Series C, you can start moving into full acceleration mode on demand. That’s when you bring in the pipeline engine. But it only works if the foundation is already there.

A fractional marketing leader isn’t right for everyone

I’m in a CMO network with an active Slack group, and fractional CMO roles are one of the most discussed topics right now. There’s real demand for it, and the model makes sense at certain inflection points. But it’s not the answer for everyone. 

Early “doer” roles—the people who are going to build your website, write the case study, run the event, manage the demand tools—those roles need to be full-time or well-structured agency partnerships. A fractional CMO can set strategy and advise on hiring, but if you drop someone into a company that doesn’t yet have the infrastructure to execute, and often the passion for building the company, you’re setting them, and yourself, up to fail.

AI implementation requires change management, like any other tool

Lots of leaders are laser-focused on AI implementation to drive revenue, but we all need to consider change management in the process. It’s something I’m working through in real time at Dataminr.

We have a power user on my team who has built 38 Claude skills. His estimated work output has nearly doubled. I also have team members with access to the same tools who are barely using them. The gap between those two people is not an issue of access or aptitude. It’s training, structure, time, imagination, and mindset. 

Dropping technology into an organization without deliberate onboarding creates silos. It improves individual productivity in pockets while the team as a whole stays fragmented. 

The approach I’d recommend—sequentially—is this: train people on the platforms first, then build job-specific skills that show them concretely how their work changes, then develop cross-functional processes so those individual gains start to compound.

As with anything that requires change management, there’s also a psychological dimension to address. People are afraid. My younger team members are asking: Is this going to replace me? We can ease these kinds of fears by investing in people’s ability to grow alongside the tech. I feel a real obligation, especially to people earlier in their careers, to help them build skills that will matter for the next twenty years.

To learn more about Wayfinders and the other advisors in the program, check out the 53 Stations website.