Your first VP of Sales probably won't be your last, and that's fine

A common conversation with founders goes like this. Someone has just let go of their first VP of Sales after eleven months and is clearly embarrassed about it, as if it reflects badly on their judgement. It rarely does. It reflects a mismatch that almost every founder makes once, usually because nobody tells them it's coming.

Early-stage commercial leadership has one of the shortest average tenures of any senior hire, and it's not because founders are bad at hiring. It's because the skill set a business needs from its first VP of Sales is almost never the skill set it needs from its third one, and most founders hire for the job title rather than the actual stage of the business.

The mismatch, specifically

A founder's first commercial leader needs to be someone who can sell personally, build the playbook from nothing, and tolerate enormous ambiguity about what's actually working. A later-stage VP of Sales needs to scale a team, install process, and operate inside a playbook that already exists. These are not the same person, and they're frequently not even the same kind of person. Hiring a polished, enterprise-trained sales leader into a pre-playbook startup is one of the most common and most expensive mismatches in early-stage hiring, the candidate isn't wrong for the title, they're wrong for the stage.

The CV that looks most impressive on paper is often the worst fit for a business that doesn't have a playbook yet. Polish and stage-fit are different things.

What the business needs A builder Comfortable with ambiguity, creates the playbook, sells personally What often gets hired A scaler Expects a playbook, installs process, manages a team
The seniority mismatch behind most early-stage commercial hires that don't work out.

Why this also happens with the first marketing hire

The same mismatch shows up almost identically with first marketing hires. Founders often hire a brand-minded marketer when what the business actually needs is someone obsessed with pipeline, proof and measurement, because there's no brand yet worth building, there's only a hypothesis worth testing. The marketer who'll thrive in that seat looks, on paper, less senior and less polished than the one who'll struggle in it.

What to do instead

Before writing a senior commercial brief, it's worth being honest about what stage the business is actually at, not what stage you'd like to be hiring for. If there's no repeatable sales motion yet, you need a builder, not a scaler. If there's no marketing engine yet, you need someone who'll get their hands dirty on channels and measurement, not someone who'll arrive expecting a team to direct.

It's also worth saying plainly to the candidate, in the interview, that this role is likely to change shape significantly within eighteen months, and asking how they feel about that. The right person for an early-stage seat is usually someone who finds that exciting rather than unsettling. If a candidate seems keen to "build out the team" in the first conversation, before there's any evidence the playbook works, that's worth probing rather than taking as a positive sign.

None of this means your first commercial hire is disposable, or that getting it "wrong" the first time is a failure. It means the job description should match the business you actually have, not the business you're hoping to become, and that's a more useful way to think about the role than worrying about how long the person stays in it.

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