Picture a conversation I’ve had some version of a dozen times. It’s illustrative, not a specific client — a composite built from the pattern.
The founder walks me through the marketing operation the way you’d walk a guest through a house you’re proud of but tired of cleaning. There’s the agency — good people, three years in, monthly retainer. There’s the demand gen manager, sharp, hired last spring. There’s the content person who ships on time. HubSpot is paid up. The webinar calendar is booked out through Q3. A rebrand landed in February. Pipeline is flat.
We sit down. I ask one question: Who decides what marketing does next quarter?
There’s a pause. Then, almost apologetically: “Honestly? I do. I sat down last month around 9pm on a Wednesday and picked the next three campaign priorities. The team executed them. They executed them well.”
That’s the moment. Not the flat pipeline, not the agency invoice, not the tool stack. The 9pm Wednesday.
Why does a $20M company end up here?
Because the fixes get bought in the wrong order.
When growth slows in the mid-market, the reflex is to buy a tactic. Agency for demand. A channel hire for paid. A tool for attribution. Each of those things works — locally. The agency ships campaigns. The hire runs the channel. The tool produces a dashboard. Every individual piece performs.
And yet nothing compounds. Six months later you have more activity, more spend, more Slack channels, and the same flat line. So you buy another tactic. Rinse.
The thing nobody tells you when you’re buying tactics is that compounding is the leadership function. It’s not something an agency produces. It’s not what a channel manager does. It’s what happens when someone owns the direction of marketing for long enough, with enough authority, to say what the next quarter is for — and, just as importantly, what it isn’t for. That’s the job of a marketing leader. Not the person who runs marketing. The person who decides marketing.
Below roughly $10M you don’t need that person; the founder is that person, and it works. At real scale you have that person; they have a title and a comp package and a seat at the exec table. Somewhere in between — usually starting around $10M–$15M, painfully obvious by $20M — the founder-as-marketing-leader model stops scaling and nobody replaces it. The tactics get replaced. The leadership doesn’t.
Why doesn’t anyone notice?
Because everyone is competent and everything ships.
This is the part that makes the gap so hard to see from inside the company. If your agency were bad, you’d fire them. If your demand gen hire were underperforming, you’d manage them out. If your tools were broken, you’d swap them. Those are visible failures with visible owners.
A leadership gap has no owner by definition. That’s what makes it a gap. The org chart looks fine — there are marketing names on it, they have titles, they show up to standups. The calendar looks fine — things ship on schedule. The reports look fine — opens, clicks, MQLs, all trending in some direction. What’s missing isn’t a person. It’s a function: the function that looks at every one of those inputs and says, “next quarter we double down on the vertical play and we stop the webinars, and here’s the theory of why.”
Without that function, the team does the reasonable thing. They keep doing what they did last quarter, slightly better. The agency proposes what agencies propose. The channel hire optimizes the channel they were hired to run. Nobody is wrong. Nobody is compounding.
Why doesn’t the agency solve this?
Because agencies are hired to execute a direction, not to set one.
I say this having worked alongside plenty of good agencies. The best of them will push back, offer strategy, bring points of view. But the commercial relationship — the reason they exist in your P&L — is that they take a brief and produce output against it. When the brief is thin, the output is still competent; it’s just aimed at whatever the agency’s default assumptions are, which are usually about the channel or the deliverable, not about your business.
Ask your agency the same question I asked the founder above: what should marketing do next quarter, and what should it stop doing? A good agency will give you a smart answer about their scope. That’s the honest answer they can give. It’s not the answer to the question. The question requires someone who sits inside the P&L, sees the sales pipeline, knows why the last three deals closed and the last three didn’t, and can trade one initiative off against another.
The same is true of a channel hire. A great paid media manager will make paid media perform. They will not — and shouldn’t be expected to — tell you whether paid media is the right bet against ABM against partner-led against founder-led content this quarter. That’s a portfolio call. Portfolio calls are leadership.
What does the leadership function actually do?
Four things, when it’s working:
It picks. Every quarter, marketing has more possible bets than budget or attention. Somebody has to choose two or three and kill the rest. Not defer them. Kill them. Founders are bad at this because everything sounds plausible at 9pm. A marketing leader is paid to say no on your behalf.
It connects marketing to revenue in a way sales trusts. Not with a dashboard. With a shared model of who we’re selling to, why they buy, what marketing is producing that sales can actually use, and where the handoff breaks. Most $20M companies have a marketing report and a sales report and no shared model. That’s a leadership vacancy, not a reporting problem.
It runs the feedback loops. Which content is producing pipeline, which campaigns are producing noise, what the last ten closed-won calls said about how they found us. This is the boring work that turns activity into compounding. It doesn’t happen unless someone owns it as their job.
It protects the roadmap from the founder. I mean this warmly. Founders in growth-pressured companies are, correctly, restless. When pipeline is flat, the instinct is to reach into marketing and change something. A marketing leader absorbs that pressure, translates the parts of it that are real signal, and holds the plan against the parts that are just Wednesday night anxiety.
A short self-check: name the gap
Not diagnostic in a clinical sense — just five questions I ask founders to sit with before we talk about what to do.
- If I asked your head of marketing (or your agency lead) what the marketing strategy is for next quarter, would you get the same answer I would? Would you get the same answer sales would?
- In the last six months, what has marketing stopped doing? Not “deprioritized” — actually stopped.
- Who owns the trade-off between short-term pipeline and long-term brand? Whose call is it, and when was it last made explicitly?
- When a deal closes, does anyone on the marketing side know why? When a deal is lost, does anyone know what marketing could have done differently?
- The last three campaign priorities — who set them, and when?
If most of these answers route back to you, the founder, you have the job. You just don’t have the time to do it. That’s not a criticism. It’s the definition of the gap.
What are the options once we’ve named the gap?
Three, roughly. The point of naming the gap isn’t that there’s one right answer — it’s that the answer becomes a real decision instead of a default drift.
Grow a director into it. If you have a strong senior IC on the marketing team who has the business instincts and just needs the altitude, promote them and support them. Cheapest option. Slowest. Works when the raw material is already there.
Hire a full-time VP or CMO. Right answer when the company is big enough, funded enough, and the marketing surface area is broad enough to justify the comp. Wrong answer when you’re buying a title to fix a diagnosis you haven’t done yet — you’ll hire the wrong profile and lose a year.
Bring in a fractional CMO. Right answer when you need the leadership function running now, at senior weight, without adding a full exec seat. Also useful as a bridge — do the diagnosis, set the direction, either hand it off to a director you grew or write the spec for the full-timer you’ll hire in eighteen months. This is what I do, so treat that as disclosure, not a pitch.
There isn’t a universally correct choice. There’s a correct choice for your stage, your team, and your economics. What’s not correct is buying another tactic while the leadership seat stays empty.
The forward-looking piece
The reason I wrote this the way I did — opening with a scene, not a definition — is that the leadership gap almost never announces itself. It shows up as fatigue. As a founder who’s tired of marketing conversations. As a team that’s working hard and producing output nobody can quite connect to revenue. As a board slide that keeps saying “invest in demand gen” without anyone being sure what that means this time.
None of that gets solved by another agency, another hire, or another tool bought in isolation. It gets solved by naming what’s actually missing, then choosing — deliberately — how to fill it. Some companies grow the person. Some hire the seat. Some run fractional for a stretch. The win, the thing that actually changes the trajectory, is the naming. Everything after the naming is a real decision made with real information, which is a different sport from the one most $20M founders are playing at 9pm on a Wednesday.
If any of the scene at the top of this post read a little too familiar, the useful next move isn’t to buy anything. It’s to sit with the self-check and get honest about which of the three options fits your company. That’s a conversation worth having with someone who’s had it before.