Questions to ask your next VP of Sales in the interview process

How do you determine if a VP of Sales candidate has the chops to be your next VP of Sales? Here are seven questions that will help you in the interview process along with a scoring system to make the decision somewhat more objective.

In the blog post “How to Hire the Right VP of Sales and What Happens if You Don’t” we described the top 6 things to look for to ensure you hire a great VP of Sales.

These questions will help you determine how your candidate stacks up.

Score each answer 0-4

0 and 1 are red flags

2 is neutral

3 is good

4 is excellent

1. How did you build your most recent sales team? Who did you hire first – why? How do you deal with miss-hires?


The first question helps you learn the techniques and process this VP of sales candidate uses as well as the extent and depth of their connections.


The first two hires are critical and should be able to happen in thirty days if your candidate has a loyal sales entourage as we described in our How to Hire the Right VP of Sales and What Happens if You Don’t” blog post.


We all make mistakes when we hire people. The key is doing something about it quickly. Nothing drags the team down faster than making a bad hire, and then not actioning the poor decision.


2. What are the three most notable deals you helped your sales team close including how you structured the contract/SOW? If you have a whiteboard and are doing an in-person interview, have the candidate go up to the board and map out the steps and who performed them.


Selling is about storytelling. A VP of Sales has to be able to get their hands dirty and help the team work deals, strategize and negotiate win-win contracts. You’ll be able to tell how hands-on this VP really is by the way they demonstrate a knowledge of the details. There should be an electric feeling in the room as they give you the blow-by-blow. By asking for three you learn if they can net it out while keeping it interesting.


3. Did all three deals lead to successful implementations? Why did they buy; i.e. what problem did you solve for them through the purchase of your solutions? And are they still customers?


I know there are three questions in one here, but VPs have to deal with a lot that gets thrown at them on a daily basis. Let’s see how they deal. Selling deals, the right way means they get successfully implemented and stay customers for life. That is what you want from your new VP of Sales.


4. Describe the sales process you use and the profile of the ideal prospect you and your team sell to?


Having an Ideal Customer Profile (ICP) is critical to ensuring sellers do not waste their time on unqualified prospects who aren’t going to buy, and if they do, will churn.



Side Note: If you are looking to hire a VP of Sales and want to accelerate their (and your) path to success, please email us at info@zebrafi.com. We work with many great ones. And we will do it for free!

VPs of Sales globally use the Zebrafi selling system to help them scale sales. We have had 13 clients who have had great liquidity events by going public, or by being purchased for many times sales.

5. Who is responsible for lead generation at your company? What is the process from Awareness to Close?


Understanding how to set up a lead generation process that creates a consistent flow of perfect profile leads is critical to success. Even if marketing is responsible for their lead generation program, the right VP of sales will teach the sales team an excellent qualification process to determine if the lead is real, winnable, and worth it.  And they’ll know how to work productively with marketing to pivot until it’s working.


6. Did you participate in helping the organization determine which markets or use cases the sales team should pursue next?


This question determines if this VP of Sales will be an asset in determining the go-to-market strategy and the tangential markets your business will pursue once they have had initial success. This question helps determine the level of maturity and depth of the candidate.


7. What was the largest sales team you ever helped build and manage? Describe how your day-to-day changed as the team grew.


This question, assuming the scores have all been a 3 or a 4 so far, will help determine how far you can go with this candidate. Some VPs of Sales prefer a startup and once the business starts to transition, they move on. Nothing wrong with this. I resemble that statement. There are not many who have managed sales teams of more than 25 reps. I have done it twice, and I know I don’t like it. How flexible is your VP of Sales candidate? These questions will help give you a glimpse of how far you can go together.

To take some of the subjectivity out of the process total the score you have from the seven questions.

Total Score:

0-16 Red (no)

17-22 Yellow (caution – are you willing to invest in them?)

> 23 Green (recommend you hire)

Other suggestions.

Although this is basic advice, you’d be surprised how many do not verify the resume and look for consistency between the resume and their social media presence.

Always verify the resume and their profile in LinkedIn and look for consistency.

Speak with an executive reference, a salesperson reference, and a marketing reference.

When you complete this process, you’ll have identified a great VP of Sales to help you grow, scale, and succeed for years to come!


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