The Top 10+ Questions to Ask a VP of Sales During an Interview (with Cheatsheet)

One of the classic original SaaStr posts was on the Top 10+ Questions to Ask a VP of Sales Candidate. All the questions still hold today, but I wanted to update them for 2025.  It’s a different world today, AI-fueled, often distributed and hybrid, and with inflation both in titles (CRO or VP Sales) and compensation expectations.

Use this updated script for hiring that first VP of Sales. It works.

Before we get there, as a reminder, I strongly recommend before you go to hire a VP of Sales (let alone a CRO) you:

• hire 1-2 sales reps (ideally 2) before you hire a VP Sales, at a minimum.
• and make them successful first.  I.e., both hitting quota.

So you can practice what you preach, and know of what you are hiring. And also to get big enough so a VP Sales can actually help, not hinder you.  A VP of Sales job is to scale sales.  Not figure it out from scratch.  Not usually.

Now if you are ready, but haven’t done it before in SaaS, here are 13 good screening questions to see if you have a real VP, Sales candidate in hand — or not.

These questions mostly don’t have right or wrong answers, but will help you determine the quality and fit of the candidates.

Bear in mind, you need to give the candidates enough data about the company (ARR, growth, # of folks, motion, etc) so they can answer.  But armed with that data and hopefully some research ahead of time, they should be able to answer them:

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.  They should at least be in the range.
2. What deal sizes have you sold to, on average and range? (If it’s not a similar fit to you, probably 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 and recruited at least a small team — pass. 50% of the job of VP of Sales is recruiting).
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 hands-on enough for your stage.  If everything is dated and pre-AI, be a bit worried).
5. Who do you know right now that would join you on our sales team?  If things progress, can I talk to them? (All good candidates should have a few in mind). Tell me about them, by background, if not name.
6. How should sales and customer success 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?  You’ll learn if they can sell in competitive environments for real or not.
8. How do you deal with FUD in the marketplace? (This will also ferret out if they know how to compete — or not).
9. Do you work with sales engineers and sales support? 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 know how to scale once you scale. So many folks can’t really run a demo or answer tougher or technical questions themselves).
10. What will my revenues look like 120 days after I hire you? (Have them 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 they understand 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).
12. What would you do your first 2 weeks on the job? Really listen here. Listen if they say unprompted that they’ll go visit customers — that’s great. That’s what you want. And if all they talk about is process? Dashboards? You’re not ready for that hire. You may never be ready in fact. So many candidates you talk to will talk about nothing but process, not customers to start. Don’t hire those ones.
13. Should the VP of Sales sell themselves when they start? Listen here, also. Really listen. Look, your VP of Sales can’t be a quota-carrying rep forever. But these days, so many VPs of Sales … don’t really want to sell anymore. So you’ve got to listen and here and see if they still want to. If they don’t want to sell, but just manage — you don’t want that hire. Not these days. Not when so many folks are burnt around, and just want to tell others what to do. And not do it themselves.

These questions aren’t magic. None of them are particularly insightful or profound — in isolation. In fact, hopefully they are kind of obvious.

But what they will do, is they will create a dialogue. The right dialogue.

From them, you’ll be able to determine: (x) if this candidate is for real, or not, (y) if this candidate can really be a true VP, a leader, a manager — or not — and take you to the next level — or not, and (z) if the candidate is a good fit for your company and space in particular.

If any of the answers aren’t good enough, trust me, just pass. If any don’t make sense, pass. And if you know more about any of these questions than the candidate does — pass. Your VP Sales needs to be smarter than you in sales, sales processes, and building and scaling a sales team.

And here’s a summary Cheat Sheet: