In my last piece, I argued that most VP Sales searches don’t fail because of the candidates — they fail because there’s no commercial infrastructure for a strong hire to walk into. I ended on a line that deserves its own article:
Even the right hire won’t fix it — especially a Fortune 500 executive who ran the machine but never built one.
That one tends to provoke a reaction. Because on paper, the Fortune 500 executive is exactly who you want. Big titles, big budgets, big brands. They’ve operated at a scale your company is trying to reach. So why would that be the wrong hire?
Here’s the uncomfortable answer: running a machine and building one are two completely different skills. And the resume that looks most impressive is often the one least suited to the job you actually need done.
The Trap of the Impressive Resume
Picture the candidate. Twenty years at a major CPG company. Ran a $500M business unit. Managed a hundred-person commercial team. Owned national accounts you’d recognize instantly. On every dimension a search committee scores, they win.
Now ask a different question: what did they actually build, and what did they inherit?
When that executive ran their $500M business, they inherited a commercial machine that already existed. The trade strategy was set. The pricing architecture was decades old. The sales org was structured, staffed, and running. The route-to-market was established. The planning cadence, the account segmentation, the data infrastructure — all of it was there before they arrived, built by people whose names nobody remembers.
Their job was to operate that machine well. Optimize it, manage it, hit the number. That’s a real skill and a valuable one. But it is not the same skill as building the machine from nothing.
Drop that same executive into a $40M brand with no trade strategy, no pricing framework, no defined sales org, and no operating rhythm, and watch what happens. They’re used to pulling levers that don’t exist yet. They ask for reports that were never built. They assume a team structure that isn’t there. They’re brilliant at running a system — and there’s no system to run.
Builders and Operators Are Different People
This is the distinction that matters most in a scaling-stage commercial hire, and the one most searches miss entirely:
An operator takes an existing commercial system and runs it well. They optimize within a structure. They’re exceptional when the machine exists and needs to be driven hard.
A builder creates the commercial system where none exists. They architect the trade strategy, design the sales org, build the pricing framework, and install the operating rhythm. They’re exceptional when there’s nothing there yet and someone has to make it from scratch.
Most leaders are strongly one or the other. The rare few who can do both are worth whatever they cost — but they’re rare, and you won’t identify them by counting the zeros on their last P&L.
This matters most for brands in the early growth phase. A company that’s just found product-market fit and is starting to scale doesn’t have a machine yet — it has momentum and a lot of open questions. That’s a builder’s environment, not an operator’s. Hiring a pure operator into an early-growth brand is the most common version of this mistake, because that’s exactly the stage where the impressive resume is most tempting and least suited to the actual work.
Here’s the part that trips up hiring teams: the biggest, most impressive resumes usually belong to operators. Because the biggest commercial systems are at the biggest companies — and the biggest companies built their machines a long time ago. The executive who ran the most impressive operation is, almost by definition, the one who inherited the most infrastructure.
How to Tell the Difference Before You Hire
You can’t diagnose builder versus operator from a resume. The titles and the numbers won’t tell you. But the right questions in an interview will. Here’s what to ask:
- “What did you build that didn’t exist before you got there?” Listen for specifics. A builder can name the system they created, explain why it didn’t exist, and walk you through how they architected it. An operator describes improvements to things that were already running.
- “Walk me through a time you had no data, no team, and no process — what did you do?” Builders light up at this question. It’s the work they love. Operators get visibly uncomfortable, because it’s the work they’ve spent a career avoiding.
- “How much of what you ran did you inherit versus create?” A self-aware candidate answers honestly. The answer reveals whether their scale came from building or from stepping into something already built.
- “What’s the smallest, messiest commercial situation you’ve personally turned around?” Scaling-stage brands are small and messy. If their proudest work was all at scale with full resources, that tells you where they’re comfortable — and it isn’t where you are.
The goal isn’t to screen out Fortune 500 experience. It’s to understand what that experience actually was. A big-company background is an asset when paired with genuine building instinct. It’s a liability when it’s pure operating experience dressed up as scale.
The Better Path: Build First, Then Hire the Operator
There’s an even cleaner solution, and it’s the one I argued for last time. Build the commercial infrastructure first — then hire the operator to run it.
When the trade strategy, pricing architecture, sales org, and operating rhythm already exist, you’ve changed the job. Now you’re not asking a candidate to build from scratch. You’re asking them to run a functioning machine — which is exactly what a strong operator does best.
Get the infrastructure built, and the Fortune 500 operator becomes the right hire instead of the wrong one. The same resume that would have failed in a chaotic environment now succeeds in a structured one. You haven’t changed the candidate. You’ve changed what they’re walking into.
That’s the sequence that works: build the machine, then hire the driver. Do it in that order and the pool of candidates who can succeed gets dramatically wider — because you’re no longer searching for the rare builder-operator unicorn. You’re searching for a great operator, and there are a lot more of those.
The Question That Saves the Hire
Before you fall in love with the most impressive resume in the stack, ask the question that actually predicts success at your stage:
Do we need someone to build the commercial machine, or run one that already exists?
If the machine exists, hire the operator — and the Fortune 500 background is a genuine asset. If it doesn’t exist yet, either find a true builder, or build the infrastructure first and bring the operator in after.
What you can’t do is hand a builder’s job to an operator and expect the title on their resume to make up the difference. It won’t. And the failure won’t show up until twelve months and one expensive departure later.
About the Author
Dan Sullivan is the founder of Sullivan Commercial Group LLC, a commercial advisory practice that partners with FMCG/CPG brands — founder-led, family-owned, PE-backed — to architect the commercial infrastructure so leadership can move from operating to scaling.
He has spent 18+ years in commercial leadership in the CPG industry. At Reynolds American, he restructured a 1,500-person sales organization to 1,200 and redesigned the route-to-market model — the infrastructure that overtook Juul and made Alto the #1 tracked electronic nicotine device in Houston, Austin, San Antonio, and Texas as a whole. He then designed the RGM strategy to maximize profitability across the full portfolio by geography — Texas first, then the Southeast, then nationally. At Republic Brands, he built the commercial machine from the ground up — hiring, sales org design, third-party execution, and data integration — the kind of build this article is about.
Most engagements start with a commercial diagnostic. Some evolve into fractional leadership. All of them start with a conversation.
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