95-year-old-ship-run-aground-off-the-west-coast-of-irelandResearch shows that companies adept at recruiting enjoyed 3.5 times the revenue growth, and 2.1 times the profit margin, of their less- capable peers.* But does your internal leadership team have the time, capacity, proven IP, or expertise needed for a truly successful executive search?

When hiring an executive, it is important to uncover his or her methods and management style to see if they will integrate into your organization. For purposes of this article, we will be concentrating on questions directed toward a VP of Sales. They could be revised to be directed toward other types of executives.

The questions are not unique. They will get the dialog moving in a direction that will assist you in discovering the real talents of the candidate and whether they can actually move your organization forward. One of the biggest factors is uncovering whether the accomplishments are his or his predecessor’s. These aren’t magical questions.

This approach will give you a starting point for a SaaS business, but it will basically work for all SaaS companies from $10,000,000 to $200,000,000.

  1. How big a team do you think we need right now, given what you know? (If they can’t answer — right or wrong — pass.)
  2. What is the range of your deals in dollar volume? (If it’s not a similar fit to you, pass. If they can’t answer fluidly, pass.)
  3. What is your approach to dealing with fear, uncertainty, and doubt (FUD) in the marketplace? (If they does not give a concise answer, his ability to compete in the marketplace will be limited.)
  4. What is the role of sales at this phase? What is the role of marketing?   How should they work together at this phase? (It is important that they understand the process of a lead funnel. Most management candidates do not understand this unless they have been a VP of Sales before.)
  5. What sales tools have you used? Which ones have you tried? What has/ hasn’t worked well? (If they don’t understand sales tools, they aren’t a real VP of Sales).
  6. How did you build your sales teams? What was the process? What challenges did you face? (If they can’t describe how they built a team — pass).
  7. Explain the customer life cycle and how sales and client success/management implementation and follow-up should work. (If they have no concept of this, this person has not managed implementation and life cycle management of a customer.)
  8. Tell me about your approach to working with sales engineers and sales support. When you have limited resources or capital, what is their role? (This will determine if they can operate efficiently at an early stage SaaS start-up successfully and if they know how to scale.)
  9. Which individuals that have worked with you in the past would join you if you came to work for us? What are their backgrounds? Quotas that they carried? (All VP of sales should have at least a few key guys. Keep in mind that recruiters make their living supplying talent and many firms will bill you for candidates that you hire that came directly from a candidate they referred if you pump them for names in the interview.)
  10. Who are the top three competitors in your last position? What were three deals you lost to the competitor? Why? What is going to separate us from these companies you lost to in the past? (If they don’t understand how to answer this question, this person will not be right for your organization.)
  11. What will be my company revenues after one quarter? 2 quarters? 3 quarters? 4 quarters? (There is no correct answer; however it will give you a glimpse of where this candidate’s goals would be. It will also reveal many wrong answers.


You should pass if the candidate’s answers to the questions do not make sense or if they are terrible. You want to hire somebody that knows more about the questions than you do. The VP of Sales should be smarter than you in building a sales team, the sales process and, yes, the actual sale itself. If he is not, you will want to pass on the candidate.