Hiring a VP of Sales: What to Ask For at Interview

Hiring a VP of Sales: What to Ask For at Interview

I posted an article last week, detailing my Top 12 Tips on How to Hire a Great Startup VP of Sales. Following its publication, a number of clients and connections requested a follow-up, detailing the hiring process and how to get the most out of interviewing for a VP Sales.

Firstly, the process must be quick enough to catch the best candidates, but thorough enough – ensuring enough buy-in from your internal stakeholders to ensure that you find the right person to grow your business. In saying this, every company is different, so each process will be different. Every candidate is different as so your process may adjust depending on who you interview. However, having a process framework in place gives a structure as well as specific criteria to measure candidates against.

Coaching, Pitching and Written Assessments

  • Can they give negative feedback when coaching their team? Use scenario-based questions and role plays to see how they would do.
  • Get them to run you through discovery presentation; a demo of their current solution. Depending on the state of your Startup, they may not be directly selling themselves, they will be coaching others on how to do so, so getting a good idea of their sales strategy important.

Sales Playbooks

  • Do they have examples of previous playbooks they have put together?
  • Would this style fit in with your business and with their peers such as marketing, product and customer success teams?

30/60/90 Day Plan

  • What is their go to market strategy?
  • What are they going to do when they arrive? How will they help grow your business? Are they expecting more support than you can give, depending on the stage of your Startup?
  • It’s okay to go further with your questioning and find out where they see themselves 6 months or a year into their role.

Behavioral Assessments

  • Not a decision-making tool by any means, but can let you know a lot about what someone’s personality is like. It can help give an indication as to how they may like to be managed, how they communicate and can help you to identify which questions you might want to ask them.


  • References from previous employers is an obvious part of any recruitment process, but gathering insight from those who have previously worked for your potential VP Sales is also important.
  • It is worth asking for reference details but also looking at LinkedIn recommendations and connections to gain insight.
  • Another layer to add to the ‘reference checking’ is to speak to previous customers! This can provide a great level of detail on how your potential VIP Sales approaches things like customer satisfaction, discount policies, their sales methodology and how they manage the entire process.

There are many other things you could add to the Startup VP of Sales hiring process and this is by no means an exhaustive list. However, with my own core experience finding and placing top-performing senior salespeople, these key things go a long way in helping to devise a recruitment process structure and they absolutely work when nailing down who to ultimately hire and most importantly, who NOT to hire.