Most VP of Sales Hires Fail. Usually Before the Interview Even Starts.
The company that cannot answer basic questions about its own GTM motion is the company that hires a VP of Sales expecting them to fix it by force of personality alone.
What you need to be able to answer before the first interview
- What is the realistic ARR goal, and is it built off actual data or pulled from the sky?
- What are the sales rules of engagement already, even informally?
- What does the current tech stack and rep headcount actually look like?
- What is the honest state of Marketing and CS support this person would inherit?
Questions that separate operators from storytellers
- Walk me through a deal you lost. What did you learn?
- How would you diagnose what is working and what is not in our current sales process?
- What is your 30/60/90 day plan?
- Tell me about a time you had to make an unpopular call.
- How do you handle an underperforming rep?
Structuring an offer serious candidates will accept
- Base vs. variable split: decide the philosophy before a candidate asks.
- Accelerators: whether commission scales up past 100% of quota, and at what rate.
- Equity mechanics: exercise window, vesting cliff, and acceleration triggers.
- Severance and clawback terms.