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How to Interview a VP Sales?

VP of Sales Interview Questions

These questions span from technical and operational to cultural. Modify them to best fit your company, product, and the candidate.

  • If you could build a sales stack from scratch, which tools would you choose?

  • What metrics do you check every day, week, month, and quarter? Why?

  • How do those numbers guide your decisions?

  • Has a strategic shift ever changed which metrics you pay attention to because? Explain.

  • How do you work with other departments in your current job? Which relationship is the most valuable to you?

  • What size ARR growth have you achieved with each company? How did you achieve it?

  • Have you experienced any challenges working with Marketing? If so, how did you overcome them?

  • Have you experienced any challenges working with Support and/or Services? If so, how did you tackle them?

  • What have been your ASPs (Average Selling Price) in each of your previous roles?

  • What motivates our buyers to purchase?

  • How would you approach recruiting and hiring for your initial team?

  • Roughly how many salespeople do you think we need right now? At what level and locations?

  • Approximately how much of your time would you devote to recruiting in this role?

  • How have you successfully managed to retain your best salespeople?

  • How did you create a high-performance cultures?

  • How have you encouraged healthy competition?

  • What are the best non-monetary ways to recognize performance?

  • Have you experimented with sales compensation? Were any of those experiments successful? Failures? What did you learn?

  • What you would accomplish in your first three months? First year? 3 years?

  • I’ll level with you: This job will be tough. [Insert description here, e.g. We’re a small, lean team, operating with few resources and working long hours.) Are you up for that?

Try to be as patient and methodical as possible to avoid hiring someone just because they look good on paper or you need a warm body. The wrong VP of Sales can cripple your startup’s trajectory and burn valuable cash.

The right VP of Sales can double your ARR in their first year.

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