Median VP Sales tenure runs about nineteen months. It is almost never the person. It is that there was no repeatable motion for them to run. Five questions and a number.
Answer honestly rather than aspirationally. The aspirational version is what produces the $300,000 mistake.
All-in first-year cost of the leader you are considering
Base plus on-target commission plus benefits. A US Series A VP Sales is typically $200,000 to $280,000.
Months of runway from today
This decides whether you can survive a hire that takes three quarters to fail.
Is your go-to-market motion written down?
Stages, qualification, sequences, call frameworks. Written well enough that a new person could run it without you in the room.
Has anyone other than a founder closed five or more deals?
If only founders can sell it, you have not proven the motion is transferable. You have proven founders are persuasive.
Do your pipeline stages have entry and exit criteria everyone applies the same way?
Without this, a new leader cannot forecast, and you cannot tell whether they are working or drowning until two quarters have gone.
Does everyone agree on who you sell to?
Ask three people independently. If the answers differ, a new leader will spend their first two quarters discovering that instead of selling.
One email with your answers and the read. No sequence, no spam, and I am the only one who sees it.
This is the free version and you should go run it. If you want a real read on what is actually happening in your go-to-market, tell me where you are stuck and I will come back to you personally, as soon as I can.