The questions you ask tell you so much, make them count!

20 Enterprise Sales Interview Questions To Hire Right

Amy Volas
8 min readMay 14, 2020


One of the things I hear most often on sales calls and kick-offs with startups who want to hire enterprise salespeople is:

“We didn’t get our last enterprise hire(s) quite right and it hurt. It’s mission-critical for us this time around.”

I wanted to know why this was so common for so many we engage with. So I dug deeper into each of their stories to learn more.

And I found this is most often because startups (self-admittedly) were looking for the wrong things in a strong hire.

I also found that the businesses we worked with who had made great hires in the past were all asking similar interview questions that looked for similar things.

Namely, in 3 specific areas:

  1. Sales Skills — do they have the enterprise sales mindset and process in addition to a proven track record to repeat their previous successes with you?
  2. Soft Skills — are they adept in dealing with people and building relationships?
  3. Culture Fit — do they believe in what you’re trying to achieve and do their career goals match the direction of your company (affects retention)?

And since another question we often get from startups is “How do we do the interview process better?”, I thought it would be best to address these concerns by sharing the 20 questions most frequently used by those who were doing this well.

20 enterprise sales interview questions.

I’ve split these questions into each of the 3 different categories above. But keep in mind that some of the best indicators of soft skills, for instance, may come from asking a question on sales skills or culture fit.

Sales Skills Interview Questions

Ask these questions to learn more about their skills, process, and track record. And most of all, that they could repeat it if they joined your team.

  • How do you earn the trust of your prospects and establish credibility? The old adage “people buy from those they know and trust” is still as true as it has ever been — even more so in enterprise sales. Ask this to make sure they value relationships and aren’t…



Amy Volas

Helping SaaS startups hire executive Sales and CS leaders without the cringe ⋆ Personally closed $100MM+ ⋆ Founder/CEO ⋆ 2 Exits ⋆ LP ⋆ Sharing lessons here