10 Great Questions to Ask a VP Sales During an Interview

Screen Shot 2013-02-25 at 4.16.07 PMReady to hire your first VP Sales?  But haven’t done it before?

Let me give you a partial interview script 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, 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).

ok let’s make it 11 actually:

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).

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 are terrible, pass.  If any don’t make sense, pass.  And if you know more about any of these questions that the candidate does — pass.  Your VP Sales needs to be smarter than you in sales, sales processes, and building and scaling a salesteam.


  1. Jason, this is an excellent post and I concur with the array of potential screening questions.

  2. #12 How would you build a sales comp plan for a SaaS company from $200K ARR to $2M ARR and beyond? right answer can vary here as well but should consider ARR, bookings / cash and CLV as the basics

    • I think it’s a solid question but IMHO, FWIW, not a Top 10 great screening question. The reason is every sales rep out of Salesforce, for example, knows how to replicate the SFDC sales comp plan — and how to talk about it very fluidly and fluently. But that doesn’t mean they can be your VPS.

  3. #11 May depend on whether there is a VP Marketing. If not, this question (or #13) could be: “Have you prepared your own marketing materials in the past? Or where these provided to you by marketing” You want to know if they can create the sales story.. or if it needs to be handed to them.

  4. I think that’s an important question for your first sales rep, who likely has to be an evangelist and a generalist. But in my experience, once you go for a real VP of Sales … you’ll need a real VP Marketing too. You don’t want or need that VPS to also be your VP Mktg.

  5. Great post Jason.

    Do you think you should hire sales people when you are selling $50-$300/mo plans? Do they tend to be more suited to larger $ sales?

    • I think you’ll find that you can do inside sales at $3000+ ACV or $300/mo as long as it’s all in-bound lead driven.

      It’s possible to do some sort of sales as low at $1000 ACV or $100/month but really only if it’s done at a very low-end level (as training ground) or is essentially glorified customer support.

      True SaaS inside sales teams don’t usually sell at ACVs < $3k or so, and $5k or so is more optimal.

  6. Billy

    With regards to the Salesforce exec example…I think the takeaway is this: avoid the “I woke up on 3rd base and thought I hit a triple” candidate. If your VP of Sales candidate has had all their success in a dominant technology machine – unless they established that dominance – then ask yourself “what is it about my 20 person startup that correlates to the position Salesforce.com is in?”

    I can answer it: None. Hire people who have been successful in startups. And think hard about hiring them before they are too successful. Of if they do have an uber startup track record, make sure they are terrified of failing in their next one. That keeps that chip on the shoulder.

    This is an incredibly hard hire to make and too many VCs make it with the ex Salesforce exec, or even Oracle exec. Those guys aren’t going to get you there. Sorry.

    • Exactly. We have another post coming up on this … hire the right Type of VP Sales, the 8 Types.

    • Agreed though it can be ever harder than this. The problem with the VPS candidate who has only done Startups that never grew to at least 20-30m ARR is they may not be able to scale and grow with you. It is tough.

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  8. I loved your blog. Thanks for sharing.
    What I want to ask is for smaller start-ups. What should you look for when hiring your first sales reps?
    A post about how to find them and what to ask them would be very helpful.


  9. abderd

    I loved your blog. Thanks for sharing.

    What I want to ask is about smaller startups or earlier phases… How should you find and recruite your first sales reps? A post about this would be very helpful.

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  13. Tommy

    Perhaps we have different terminology outside the States | what are FUD and SFDC sales comp plan…? cheers.

    • FUD is Fear, Uncertainty and Doubt. A standard if slightly stomach turning sales tactics of telling half-truths about your competitors to scare prospects away.

      SFDC is the company Salesforce.com

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