10+ Questions to Ask If You’re Interviewing for a VP of Sales Role

Dear SaaStr: I am a candidate for a VP Sales job. What are great questions to ask the CEO?

I’m involved at any given time with 2-3 VP of Sales and CROs searches across SaaStr Fund portfolio companies.  One thing is common across all of them: I am shocked how little candidates really know about what they are potentially getting themselves into.  Truly, honestly shocked how little they really know about roles they are very close to taking.  Even the smartest and sharpest candidates in many cases.

If you’re a candidate for a VP of Sales role, asking the right questions during the interview is critical—not just to impress the CEO, but to ensure the role is the right fit for you.  Way too often, a good candidate just takes the wrong role.  It’s sad because somewhere else, they could have thrived.  I blame the CEO more here, because they have more information.  But also, often the CEO doesn’t really know what to expect from their first (or even second or third) VP of Sales.  So …

Here are some great questions to ask:

1. What is the current ARR, and what is the growth target for the next 12 months?
   This helps you understand the scale of the business and the CEO’s expectations. If the growth target is unrealistic based on the current trajectory, that’s a flag.  At least talk honestly and openly about it.  I’m shocking how many VP of Sales and CRO candidates I talk to don’t really understand the plan for the next 12 months.  Not really.

2. What is the sales team structure today?
   Find out how many reps are on the team, their performance, and whether there’s a proven sales motion in place. If the team is underperforming or there’s no structure, you’ll need to assess whether you can fix it quickly.  Find out now.

3. What is the lead flow like?
   Ask about the volume and quality of leads coming from marketing. If the pipeline is weak, you’ll need to build it from scratch, which is a very different challenge than scaling an already functional sales engine.

4. What is the CAC payback period?
   This gives you insight into the company’s unit economics. If the CAC payback is too long (e.g., over 24 months), it might indicate inefficiencies in the go-to-market strategy.

5. What is the churn rate?
   High churn can make hitting sales targets nearly impossible. If customers are leaving faster than you can acquire them, you’ll need to address that before focusing on growth.

6. What is the relationship between sales and marketing?
   Misalignment between sales and marketing is a common issue. Ask how the teams collaborate and whether there’s a shared understanding of goals and metrics.  Way too many first time VP of Sales especially know little about how marketing works at startups they are talking to.

7. What is the average deal size and sales cycle?
   This helps you understand the complexity of the sales process and whether it aligns with your experience. Selling $10K ACV deals is very different from selling $100K+ enterprise deals.

8. What is the biggest challenge the company is facing in sales today?
   This question shows you’re thinking strategically and want to solve real problems. It also gives you a sense of what you’ll be walking into.  I’m again shocked how often candidates I talk to — have no idea.

9. What does success look like in this role?
   Ask the CEO to define what success looks like for the first 90 days, 6 months, and 12 months. This will help you gauge whether their expectations are realistic.

10. What is the company’s funding situation and runway?
    You need to know how much cash the company has and whether it’s in a position to invest in growth. If the runway is short, you’ll face pressure to deliver results quickly, often without adequate resources.

11. How do you see the relationship between the CEO and the VP of Sales?
    This is a critical one. You want to understand how involved the CEO will be in sales and whether they’ll give you the autonomy to lead.  Look, you may not learn much by asking this.  But you’ll learn something that matters.

12. What is the company’s vision for the next 3-5 years?
    I sort of hate this question when it’s asked too early in the interview process, because it’s so generic it sounds lazy.  But ask about 30 minutes in.  This helps you understand whether the CEO has a clear plan for the future and whether it aligns with your career goals.

13. What is the sales tech stack?
    Ask about the tools the team is using. If the tech stack is outdated or nonexistent, you’ll need to invest time and resources to modernize it.  The tech stack isn’t everything, but it will give you a sense of what you are walking into.

14. What is the company’s competitive positioning?
    Understanding how the company differentiates itself in the market is crucial. If the CEO can’t articulate this clearly, it’s a flag.  It also will show you if the type of competitive selling involved is right for you.  If you haven’t sold in a very competitive environment, be way of entering one that is.  It’s just a different playbook.

15. Why did the last VP of Sales leave?
    This can give you insight into potential challenges in the role or with the company culture.  I find most VPs of Sales and CROs are fine asking this question, but it can make CEOs uncomfortable.  It shouldn’t.  Being honest here is best for everyone.  Any top VP Sales candidates just want to learn why.  Most will be up for the challenge if they know why and if it’s a good fit.

And before you ask all these questions — spend enough time to really understand the product.  Way too many candidates … don’t.  You can’t really have a good conversation here if you don’t truly understand the product first.

And for the other side, here are 10 questions CEOs can ask VPs of Sales during the interview process: