Here’s What Nobody Tells You

A few years ago, I watched a scrappy, high-growth brand hire a former colleague of mine — a marketing director straight out of a massive CPG conglomerate. On paper, she was brilliant, armed with the rigorous strategic toolkit that builds billion-dollar portfolios and the founders were ecstatic to finally have “grown-up” leadership in the room.

Yet, despite that promise, she didn’t last long.

While I never learned the specific details, I suspect the culprit was the same structural mismatch I’ve seen time and again. She likely arrived ready to implement the slow, methodical architecture of a legacy corporation, while the founders were still operating on gut instinct and speed. In that environment, a five-year brand roadmap feels like a distraction to a leader who just needs someone to roll up their sleeves, execute tactics and move product.

Having spent my career navigating this tension, I’ve realized that when these relationships fracture, the industry likes to whisper that the founder simply couldn’t “let go.” But that diagnosis is lazy because the friction rarely stems from an inability to cede control; it comes from a misunderstanding of physics. Marketing in these environments isn’t just about managing a department; it is about managing a high-stakes transfer of identity.

The $50 Million Illusion

There is a predictable inflection point where a founder looks at their growing business and decides it’s time to hire a “real” marketer. The mistake they often make is hiring for the company they want to be rather than the company they are.

In my experience, until a CPG brand hits the $50 million revenue mark, it rarely needs a high-level strategic CMO. At that stage, you are likely still a sales-led organization. Your primary hurdle isn’t “brand love” — it’s distribution. You need boots on the ground and a relentless fight for shelf space.

But when a strategist enters before that critical mass, they naturally look for leverage — positioning and storytelling — while the business is still screaming for commercial brute force. This leads founders to recoil because they are watching their expensive new leader build slide decks about brand purpose while the sales team just needs a better sell sheet. They crave the legitimacy of a “grown-up” function but underestimate how much that function will gum up the gears of their operation.

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The Trap of ‘Grit’

Even if the timing is right, you still have to navigate a clash of worldviews. Founders build companies on the belief that grit can bulldoze through any obstacle. They operate on a mentality of effort, whereas marketers are trained to optimize for efficiency.

I learned this the hard way early in my career at ThinkThin. We were hosting an event at Expo West when the founder asked me to “live tweet” the session to drive PR. Logically, I knew this was a waste of resources; we had no Twitter following, and consumers didn’t care about an industry trade show.

But when I pushed back with logic, I missed the point entirely. The founder wasn’t looking for ROI; they were operating on the hustle mentality that had built the business. By quoting engagement metrics, I wasn’t just debating tactics; I was challenging the very survival instinct that had kept the company alive.

The ‘Saturday Night’ Text

This friction inevitably bleeds into personal boundaries, manifesting in the “Saturday Night Text.” It happens to almost every marketing leader in this space: your phone buzzes on the weekend with a screenshot from the founder, asking about a social post that went up hours ago.

It is easy to dismiss this as toxic micromanagement, but you have to practice empathy. To a founder, that brand isn’t a corporate asset; it is their reputation, their history and often their financial lifeline. When they see a post they didn’t approve, they feel an existential loss of control over their own voice.

That’s why the hardest transition in these companies is the shift from “I approve everything” to “I don’t have time to approve everything.” The only way to survive it is to stay attached at the founder’s hip. In a large corporation, you can operate on an island as long as you hit your KPIs. In a founder-led startup, you operate on trust. You need to be in the room advocating for your agenda every day, because that proximity is what gives the founder the confidence to finally step back.

The Translator, Not the Savior

Ultimately, the most volatile conflicts arise when the brand needs to evolve beyond the founder’s personal preferences. I faced this when a founder rejected a necessary rebrand because it felt too “corporate” and didn’t reflect his personal identity. He was struggling to separate himself from the entity he had built, unable to see that for the brand to scale, it eventually had to become its own beast.

Navigating this requires accepting a hard truth: you were not hired to “fix” the founder. You were hired to scale them.

The founders who built these companies didn’t do it with focus groups. They did it with a raw, messy intuition. Your job isn’t to bury that intuition under process — it is to build the infrastructure that allows it to travel further than the founder can reach alone. If you can check your ego and respect the gut that built the business, you won’t just keep your job. You will build the kind of brand that corporate structure can’t replicate — one that still has a soul.