Edited excerpt from Jason Lemkin in 10 Great Questions to Ask a VP Sales During an Interview:
1. How big a team do you think we need right now, given what you know? (If he/she can’t answer — right or wrong — pass).
2. What deal sizes have you sold to, on average and range? (If it’s not a similar fit to you, pass. If he/she can’t answer fluidly, pass).
3. Tell me about the teams you’ve directly managed, and how you built them. (If he/she can’t describe how they built a team — pass).
4. What sales tools have you used and what works for you? What hasn’t worked well? (If they don’t understand sales tools, they aren’t a real VP Sales).
5. Who do you know right now that would join you on our sales team? (All good candidates should have a few in mind). Tell me about them, by background if not name.
6. How should sales and client success/management work together? (This will ferret out how well he/she understands the true customer lifecycle).
7. Tell me about deals you’ve lost to competitors. What’s going to be key in our space about winning vs. competitors?
8. How do you deal with FUD in the marketplace? (This will ferret out if they know how to compete — or not).
9. Do you work with sales engineers and sales support? If so, what role do they need to play at this stage when capital is finite? (This will ferret out if he/she can play at an early-stage SaaS start-up successfully — and if he knows how to scale once you scale).
10. What will my revenues look like 120 days after I hire you? (Have him/her explain to you what will happen. There’s no correct answer. But there are many wrong answers).
11. How should sales and marketing work together at our phase? (This will ferret out if he understands lead generation and how to work a lead funnel. Believe it or not, most candidates don’t understand this unless they were really a VP Sales before).