15 Questions VPs of Sales Should Ask CEOs. Before They Take That Job.

"Why did the last VP of Sales leave? Just Ask."

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.

The worst outcome in many ways is a great VP of Sales that ... takes the wrong role. That's just bad and sad all around.

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 red flag. And dig in here. Just ask what the assumptions are to get there, and what's being expected of you.

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.

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. Way too many candidates I talk to actually have no idea what the lead flow is really like.

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. That may be OK if the start-up is well funded, but it's a good discussion topic.

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. Or if there really is a marketing team at all. Sometimes, "marketing" doesn't really support sales at all.

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.

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.

12. What is the company’s vision for the next 3-5 years?
    This helps you understand whether the CEO has a clear plan for the future and whether it aligns with your career goals. Just don't make this the first question. It looks like you are phoning it in if you do. Make the first 3 questions show you've done your homework on the company.

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. It's not the end of the world, but it helps to understand what you are walking into.

14. What is the company’s competitive positioning? When do you win, and when do you lose?
    Understanding how the company differentiates itself in the market is crucial. If the CEO can’t articulate this clearly, it’s a flag.

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. Just ask. You may make the CEO uncomfortable, but it's OK. All the best revenue leaders just ask. They get it. They get this is their shot to do better. And the best ones are confident they can.

These questions will not only help you evaluate the opportunity but also demonstrate that you’re a strategic thinker who understands what it takes to build and scale a successful sales organization.

And remember, you’re interviewing them as much. The worst thing that happens for >everyone< is a great VP of Sales accepts the wrong role. And bounces.

Too often it's just a mis-match. Make sure it isn't.

And finally, if you are close to taking a role, whatever you do, join some sales calls first. Listen to Gongs during the interview process, but also join 1-2 calls before you start.

You will learn so much.