The Decision I Kept Putting Off: A Mid-Market CEO’s Notes on Buying Marketing Help

It was a Tuesday night in October when I finally admitted the problem was mine.

We had lost a deal that afternoon to a competitor I consider beneath us. Better product on our side, better references, better people. When I asked the prospect’s team what happened, the answer had nothing to do with any of that. They said the other firm “kept showing up.” In their inbox, in their search results, in an industry newsletter, even in the answer one of their analysts got when she asked an AI tool to list firms like ours. We showed up once: in the meeting we were invited to.

I run a company doing a little north of $30 million. I can read a balance sheet upside down, I can walk our shop floor and spot a problem in four minutes, and I have personally closed our twelve largest accounts. And I was sitting at my kitchen table at eleven at night realizing I could not answer a simple question: what should I actually buy when I buy marketing?

Everyone had an answer, and every answer was their own reflection

Here is what nobody tells you about this decision: the moment you start asking, you are surrounded by confident people whose advice happens to match what they sell.

I called a friend who runs an agency. He made a compelling case for an agency. I had coffee with a consultant I respect. She made an equally compelling case for a fractional CMO. A peer in my CEO group told me to just hire a marketing director and be done with it, which is what he did, and I did not have the heart to point out that he complains about his marketing at every single meeting.

Each pitch sounded right while I was hearing it. That was the unsettling part. I make build-or-buy decisions all the time in operations, and I know what good looks like. Here I had no instincts at all, just a history that made me cautious: we had spent real money on marketing before. A website project that ran long, a few campaigns someone talked me into, a sponsorship I still cannot explain. Six figures over a few years, and if you asked me what it earned us, my honest answer would be a shrug. I was not afraid of spending. I was afraid of spending blind again.

The question that changed the conversation

The turn came from an unexpected direction. I was venting about all this to someone who advises companies on marketing, fully braced for pitch number four. Instead she asked me one question: “Before we talk about who you should hire, tell me what you already have.”

I started listing. We have a marketing coordinator, sharp, early in her career, who mostly makes sales decks and keeps the website from embarrassing us. We have me, doing what I now understand was impersonating a marketing strategist on nights and weekends. That was the whole inventory.

She drew two columns on a napkin. One said strategy: the plan, the priorities, the thing that connects marketing activity to revenue. The other said execution: the hands that actually produce the work. Then she said something I have repeated to at least five other CEOs since: every marketing purchase that goes wrong goes wrong the same way. You buy one column assuming the other one exists somewhere in your building, and it does not.

Suddenly my whole history made sense. The website project, the campaigns, the sponsorship: all execution, bought with no strategy column behind them. And my peer with the unhappy marketing director had bought one overworked person and asked him to be both columns at once.

What I’d tell the CEO sitting at that kitchen table

I will not pretend I solved this in a weekend. But the decision stopped feeling like a bet the moment I stopped asking “which vendor is best” and started asking “which column am I missing.” Those are different questions, and only the second one has an answer you can defend to your board.

In our case the honest inventory said we were missing both. One coordinator is not an execution team, and a CEO moonlighting as a strategist is not a strategy. Once I could say that out loud, comparing the options got almost mechanical: what does each one actually supply, what does it cost against a hire, and what has to already exist in my building for it to work. The anger about the deal we lost turned into a plan with numbers in it.

If you are where I was, do the inventory before you take a single pitch meeting. Write down who in your company sets marketing priorities against revenue goals, and who produces the work. If you have one column, buy the other. If you have neither, buy them together and make one party accountable for the whole. And whatever you do, do not grade your options on how confident they sound in the meeting. I have been the most confident guy in the room on subjects I knew nothing about. Usually on marketing.

The CEO in this piece is a composite, drawn from conversations we have with company leaders every week. The kitchen-table math, the conflicting pitches, and the lost deal are all real; only the names are missing.

If you are in the middle of this same decision, we wrote the complete version of the napkin: Agency, Solo Consultant, or Complete Marketing Department: The Three Ways to Buy Marketing Help covers what each option costs in 2027, when each one is the right call, and the questions to ask before you sign anything. And if you would rather talk it through, book a 30-minute fit conversation: we will tell you which way to buy, even when the answer is not us.