Sales leadership
Why Your VP of Sales Left
A VP of Sales leaving is rarely just a people problem. More often the seat was impossible: no clear number, no playbook, a motion that was not ready, or a founder who never truly handed over the wheel. Before you hire the next one, understand what actually broke, or you run the same loop again at six months and another lost year.
It is usually the seat, not just the person
A strong VP of Sales cannot win inside a broken system. If the ICP is fuzzy, there is no playbook, the pipeline is not real and marketing is not aligned, even a great hire spends their ramp firefighting instead of building. They miss the number they were set up to miss, and then they leave, or you let them go.
The pattern repeats because the diagnosis is wrong. Founders conclude they hired the wrong person and hire again for the same impossible seat. The fix is to make the seat winnable first.
The real reasons VPs of Sales leave
Hired too early, before founder-led sales found a repeatable motion, so the VP is asked to scale something that does not work yet. Hired with no air cover, owning a number while strategy, pricing and marketing sit outside their control. Hired into chaos, with no playbook, no clean CRM and no reliable forecast. Or hired by a founder who keeps taking the big deals back, so the VP never really owns sales.
Compensation and title gaps matter too, but they are rarely the root cause. The root cause is almost always that no one built the engine the VP was supposed to run.
What to do before you hire the next one
Separate the two questions: was the person wrong, or was the system? Diagnose the motion honestly, the ICP, the playbook, the pipeline, the forecast and the founder handoff, and fix what made the seat impossible. Only then does it make sense to hire, because now the VP inherits a system that can win.
This is where a fractional CRO earns its keep. Someone senior comes in, owns the number, rebuilds the engine, and either stabilizes it until your next VP can run it or helps you hire the right one into a seat that finally works. You stop paying for the same failed hire twice.
Common questions
Should I replace my VP of Sales or fix the system first?
Fix the system first, almost always. Rebuild the motion, pipeline and forecast, and you find out fast whether the VP was the problem or the symptom. Replacing a person inside a broken seat just resets the clock on the same failure.
How soon is too soon to hire a VP of Sales?
Before founder-led sales has found a repeatable, documented motion. If the founder is still the only person who can close, a VP inherits guesswork and leaves. Prove the motion first, then hire someone to scale it.
My VP of Sales keeps missing the number. Is it them?
Maybe, but check the seat first. No playbook, a fuzzy ICP, an unreal pipeline or a founder who takes deals back will sink a strong VP. Diagnose the system before you blame the person.
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