I was walking downtown to a meeting last week. Headphones in, trying to make good time without rushing. Taking space to think. This is how I move through most days. I like the way walking gives my thoughts room to stretch.
As I walked, I listened to a new podcast, “Long Strange Trip“. It’s a series of interviews with CEOs from different industries, at different stages, with vastly different personalities. But the same theme kept coming up in one form or another: The job changes.
Not once. Repeatedly.
What makes someone effective as a founder, or as a first-time CEO, doesn’t stay effective forever. In fact, the very instincts that got them here can quietly become the thing holding the company back.
The Part Founders Rarely Say Out Loud
Across the podcast episodes, whether with a startup founder or a public-company CEO, the most honest moments sound something like this:
I had to stop doing the job the way I used to.
I had to let go of being the person with the answers.
I had to change how I saw myself.
That lands with me because I’ve spent my whole career inside organizations where roles were constantly evolving. (Maybe that’s just marketing. Maybe that’s just the world.) Nonprofits. Hyperscale hardware. Edtech, govtech, fintech, SaaS. International work and very local work. My masters studies, focused on leadership. The throughline across all of it wasn’t industry. It was adaptation.
The leaders who lasted were the ones who held onto their principles while staying flexible about how they showed up. Founders, in particular, often struggle here. I see it all the time. And it’s totally understandable.
Many of them built their companies by being exceptionally good at doing things themselves. Selling. Shipping. Writing. Closing. Fixing. That self-reliance isn’t a flaw. It’s a strength. Until the organization grows large enough that individual excellence stops scaling. (And that’s earlier than many think.)
At that point, the job quietly changes. And pretending it hasn’t is usually what creates the most friction.
Why Marketing Feels So Fraught at This Stage
This is usually where marketing enters the conversation. And it’s where practitioners are most misunderstood.
Founders will tell me, sometimes apologetically, sometimes proudly, that they can handle marketing themselves. They’ve written the website. They’ve run campaigns. They’ve sold to friends and friends of friends. They know their product better than anyone. And all of that can be true. It often is true.
The problem isn’t competence. It’s perspective.
When marketing sits at a leadership level, it does something very specific. It interprets signals across the business and the market at the same time. Sales performance. Financial pressure. Buyer hesitation. Competitive noise. Internal capacity. External trust.
Marketing is often the first place where misalignment shows up. Not because marketing is broken, but because it touches everything.
Here’s the thought I keep coming back to after listening to the podcast & sitting, for years, with leadership teams:
Marketing doesn’t create clarity. It reveals whether it already exists.
When a company is at an inflection point, marketing is where you see the cracks first. Messaging gets fuzzy. Priorities multiply. Sales fizzle. Everyone wants growth, but no one agrees on what kind, or at what cost.
That’s not a marketing failure. It’s a leadership moment. An opportunity.
The Outsider–Insider Role I (Get To) Play
This is where my work as a Fractional CMO lives. I partner with founders, CEOs, and heads of sales or finance who are navigating exactly those moments. Not just as a cheerleader. Nor as a fixer. And never pretending to be neutral.
My role is an outsider–insider, by design.
I’m close enough to understand the pressures, the personalities, and the politics. Far enough away to see patterns without tinted glasses or corporate inertia. I bring what I’m seeing across the organization, what I’ve seen work elsewhere in similar moments, and what the market is signaling, even when it’s uncomfortable.
Sometimes that means reflecting back what leaders already sense but haven’t named yet. Sometimes it means slowing things down when urgency is masking confusion. Often it means helping a founder recognize that the job they’re trying to do is no longer the job the company needs.
This comes up just as clearly in service organizations. Law firms. Professional services. Any place where the business is personality-driven and the leaders have never trained to think about marketing or management as systems. The dynamics are the same. The stakes just wear different clothes.
Reinvention Can Happen Without Burning Everything Down
One thing I appreciate about the Sequoia conversations is how undramatic the best reinventions sound. No grand pivots. No manifesto moments. Just leaders recognizing that the way they operated before wasn’t going to carry them forward.
Reinvention doesn’t have to mean chaos. It can be quiet. It can be supported. It can look like inviting in a different kind of perspective, or creating space for someone else’s judgment to matter.
The leaders who navigate inflection points well aren’t the ones who cling to being indispensable. They’re the ones who let the job change without losing themselves or their teams in the process.
That’s the work I’m interested in supporting.
Not louder marketing. Not more motion for its own sake. Just clearer mirrors, steadier systems, and decisions made with eyes open.
Most of the leaders I work with are already there. They just need someone to help them see it clearly enough to move forward.