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, interestingly.  I wanted to update it for today, and yes there’s been some inflation.  So it’s really 13 questions now 🙂

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

Ready to hire your first VP Sales?  But haven’t done it before? Let me give you a partial interview checklist that may help a bit.  You’ll have to vary it for different types of SaaS businesses — a bit.  But it will basically work for all SaaS companies from, say, $200k in ARR to $10m in ARR or so — a wide range.  (After that, you’ll probably be looking for a different type of VP Sales.  We’ll get there in our next and final VP Sales post.)

Before we get there, as a reminder, I strongly recommend you hire 1-2 sales reps (ideally 2) before you hire a VP Sales, at a minimum.  And make them successful first.  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.  More here in our prior VP Sales posts: When You Hire Your First Sales Rep — Just Make Sure You Hire Two and here: What a Great VP Sales Actually Does.  Where The Magic Is.  And When to Hire One.

Now if you are ready, but haven’t done it before in SaaS, here are 10 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:

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, 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 a 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).

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 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?

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).

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.  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.

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