72. What are the best questions to ask a VP of sales during an interview? SALES First, let me tell you, I think you are making a big mistake hiring a VP Sales as your first sales hire. You’re not ready IMHO. Instead, I think you should hire 1-2 experienced individual reps first, manage them yourself, and learn how sales should work in your company. Then, hire a VP Sales to manage those guys and scale from there. Having said that, here are 10 good screening questions to see if you have a real VP, Sales in hand -- or not -- for a SaaS start-up post-traction but < $10m ARR or so. These questions mostly don’t have right or wrong answers, but will help you determine the quality and fit of the candidates: 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 life cycle). 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? 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 they knows how to scale once you scale). SAASTR.COM 69