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Head of Sales – Sample Interview Questions

By Lead Edge & True

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This post was created in collaboration between Lead Edge Capital and True, a data-driven recruiting firm with offices across the U.S. and in Europe.

ROLE: Head of Sales

Sample Interview Questions

  • Assess how competitive, hungry, courageous they are.  Were they competitive athletes? Have they won President’s club awards or exceed quotas regularly? Have they done something exceptional that required dedication/hard work/relentless determination.
  • How do they hire, mentor, retain/reward and fire their team.  Have them provide specific examples of how they have hired, how they have coached their team and how they have fired under-performers.  Also ask who has followed them in prior/current jobs (who would be the first 3 people he/she would hire). What is their hiring methodology?  How do they build & drive culture?
  • What are examples of successful Go-To-Market strategies that they have built?  Also test for bets that weren’t right and test for course-correction (they don’t always have to be right, but they should quickly spot the winning story, discuss with the Exec team and allocate resources appropriately).
  • What systems have they built / optimized?  Do they have a repeatable process?  Do they collaborate with Marketing, Lead Gen and Product? Do they present to the Board & CEO?
  • Do they personally sell deals themselves or have they moved into a pure management role? Are they hunters or farmers?
  • Are they selling to similar customers? Selling similar velocity?  Similar deal sizes/structure?
  • How big a team do they think they need immediately?
  • Who were/are their mentors?

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