32 VP of Sales Interview Questions to Help You Find the Perfect Candidate

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Dan McDermott
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Choosing the right VP of Sales for your team is one of the most important (and trickiest) decisions a founder can make for a developing company. 

The right VP Sales can level up your sales, drive long term growth, and make it all seem easy. 

The wrong person, though, can actually hurt your sales organization while costing you vital time and money. The opportunity cost of having the wrong person in place is dramatic. 

Unfortunately, most VPs of Sales don't last long - on average, people in the role last only 17 months. Imagine committing a high comp package, handing over the keys to the castle, and then realizing things aren't going well....a year and a half later

But, don't worry! In this article, we'll lay out a series of interview questions that you can use to help identify the VP of Sales that your company needs right now. 

Interview Questions for VP of Sales

As you interview candidates for the VP of Sales position, it's important to ask the right questions to assess their experience and skills in sales leadership and strategy.

Here are some interview questions that can help you find the perfect candidate:

1. Can you describe a time when you successfully developed and executed a sales strategy? What were the key elements of the strategy and how did you measure its success?

2. How do you motivate and inspire your sales team to achieve their targets? Can you provide an example of a time when you were able to drive exceptional performance from your team?

3. What steps do you take to identify and pursue new business opportunities? Can you share a specific example of how you successfully expanded your company's customer base?

4. How do you approach sales forecasting and pipeline management? Can you explain your process for setting sales targets and tracking progress towards those targets?

5. Can you describe a time when you had to navigate a challenging sales situation or overcome a major sales obstacle? How did you handle it and what was the outcome?

6. How do you stay updated on industry trends and changes in the market? Can you provide an example of how you used market insights to drive sales growth?

7. How would you define a successful sales strategy?

8. Can you provide an example of a sales strategy you have implemented in the past and the results it achieved?

9. How do you ensure that sales strategies are effectively executed by the sales team?

10. Have you ever turned around a struggling sales team? If so, what steps did you take to improve their performance?

11. How do you motivate a sales team that is facing challenges and struggling to meet targets?

12. We are planning on growing quickly - how would you handle this from a training/coaching perspective?

13. How do you set people up for success now? How would that change if the team triples in size? How would this affect culture?

14. How would you create unified, standardized sales processes and tactics? 

15. What strategies do you employ to identify and address the root causes of underperformance in a sales team?

16. What were a couple of your best hires? What impact did they have?

17. What were a couple of your worst hires? What impact did they have?

18. What's the X factor behind getting top talent to join your team?

19. Salespeople are notoriously good at selling themselves - how can you separate specific market experience from someone's sales skills?

20. How do you build strong relationships with clients and partners?

21. Can you provide an example of a time when you successfully maintained a long-term relationship with a key client or partner?

22. How do you ensure that the sales team is effectively building and maintaining relationships with clients and partners?

23. What steps do you take to successfully launch a new product or enter a new market?

24. Can you share an example of a time when you successfully launched a new product or entered a new market?

25. How do you assess the potential risks and challenges of launching a new product or entering a new market, and how do you mitigate them?

26. How do you approach sales forecasting and setting targets for the sales team?

27. Can you provide an example of a time when your sales forecasts and targets were accurate and helped drive success?

28. How do you ensure that sales forecasts and targets are realistic and achievable?

29. How do you create a positive and motivating work environment for the sales team?

30. Can you share an example of a time when you successfully created a winning environment for a sales team?

31. How do you handle conflicts and challenges within the sales team to maintain a positive work environment?

32. How would you gauge whether our growth/scaling is too fast? Too slow? 

More Resources on VP of Sales

Jason Lemkin of SaaStr is one of the best voices in our space when it comes to understanding the nuances of hiring sales leadership. 

In addition to our 32 questions above, you should check out Jason's 10 Great Questions to Ask a VP Sales During an Interview (it's actually 11 questions): 

Here are the questions from the video:

1.  How big a team do you think we need right now, given what you know?  

2.  What deal sizes have you sold to, on average and range? 

3.  Tell me about the teams you’ve directly managed, and how you built them. 

4.  What sales tools have you used and what works for you?  What hasn’t worked well?  

5.  Who do you know right now that would join you on our sales team?  

6.  How should sales and client success/management work together?  

7.  Tell me about deals you’ve lost to competitors.  

8.  How do you deal with FUD in the marketplace?  

9.  Do you work with sales engineers and sales support?  If so, what role do they need to play at this stage when capital is finite?

10.  What will my revenues look like 120 days after I hire you?  

11.  How should sales and marketing work together at our phase?  

You can follow Jason on LinkedIn, in addition to the YouTube channel above. 

Ready to Hire a VP of Sales?

Asking the right interview questions when hiring a VP of Sales is crucial. It allows you to assess their understanding of sales strategies, their ability to turn around a struggling team, and their skills in building and maintaining relationships. 

But, you've also got to ask yourself, "Am I setting this person up for success?".

A VP of Sales can be transformative to your team, but if you throw them into a chaotic mess or a situation with zero fundamentals in place....even a superstar will struggle.

Instead, it's much better to have your sales team "built" - at least to a basic level - before bringing in the VP of Sales. That way, they can simply take over the team and focus on scaling it while optimizing your processes. 

Use the questions in this article to evaluate your candidates and find the best fit for your team. If you have any other questions about developing your sales strategy and growing your sales,  schedule a free growth audit with Kyle here.

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Dan McDermott

Dan McDermott, our Chief Marketing Officer, is a seasoned copywriter and strategist who has helped over 500 businesses carve out a competitive edge. With a career spanning nearly 20 years, Dan has fine-tuned the art of developing compelling messaging that accentuates a business's strengths, setting it apart from competitors.

Choosing the right VP of Sales for your team is one of the most important (and trickiest) decisions a founder can make for a developing company. 

The right VP Sales can level up your sales, drive long term growth, and make it all seem easy. 

The wrong person, though, can actually hurt your sales organization while costing you vital time and money. The opportunity cost of having the wrong person in place is dramatic. 

Unfortunately, most VPs of Sales don't last long - on average, people in the role last only 17 months. Imagine committing a high comp package, handing over the keys to the castle, and then realizing things aren't going well....a year and a half later

But, don't worry! In this article, we'll lay out a series of interview questions that you can use to help identify the VP of Sales that your company needs right now. 

Interview Questions for VP of Sales

As you interview candidates for the VP of Sales position, it's important to ask the right questions to assess their experience and skills in sales leadership and strategy.

Here are some interview questions that can help you find the perfect candidate:

1. Can you describe a time when you successfully developed and executed a sales strategy? What were the key elements of the strategy and how did you measure its success?

2. How do you motivate and inspire your sales team to achieve their targets? Can you provide an example of a time when you were able to drive exceptional performance from your team?

3. What steps do you take to identify and pursue new business opportunities? Can you share a specific example of how you successfully expanded your company's customer base?

4. How do you approach sales forecasting and pipeline management? Can you explain your process for setting sales targets and tracking progress towards those targets?

5. Can you describe a time when you had to navigate a challenging sales situation or overcome a major sales obstacle? How did you handle it and what was the outcome?

6. How do you stay updated on industry trends and changes in the market? Can you provide an example of how you used market insights to drive sales growth?

7. How would you define a successful sales strategy?

8. Can you provide an example of a sales strategy you have implemented in the past and the results it achieved?

9. How do you ensure that sales strategies are effectively executed by the sales team?

10. Have you ever turned around a struggling sales team? If so, what steps did you take to improve their performance?

11. How do you motivate a sales team that is facing challenges and struggling to meet targets?

12. We are planning on growing quickly - how would you handle this from a training/coaching perspective?

13. How do you set people up for success now? How would that change if the team triples in size? How would this affect culture?

14. How would you create unified, standardized sales processes and tactics? 

15. What strategies do you employ to identify and address the root causes of underperformance in a sales team?

16. What were a couple of your best hires? What impact did they have?

17. What were a couple of your worst hires? What impact did they have?

18. What's the X factor behind getting top talent to join your team?

19. Salespeople are notoriously good at selling themselves - how can you separate specific market experience from someone's sales skills?

20. How do you build strong relationships with clients and partners?

21. Can you provide an example of a time when you successfully maintained a long-term relationship with a key client or partner?

22. How do you ensure that the sales team is effectively building and maintaining relationships with clients and partners?

23. What steps do you take to successfully launch a new product or enter a new market?

24. Can you share an example of a time when you successfully launched a new product or entered a new market?

25. How do you assess the potential risks and challenges of launching a new product or entering a new market, and how do you mitigate them?

26. How do you approach sales forecasting and setting targets for the sales team?

27. Can you provide an example of a time when your sales forecasts and targets were accurate and helped drive success?

28. How do you ensure that sales forecasts and targets are realistic and achievable?

29. How do you create a positive and motivating work environment for the sales team?

30. Can you share an example of a time when you successfully created a winning environment for a sales team?

31. How do you handle conflicts and challenges within the sales team to maintain a positive work environment?

32. How would you gauge whether our growth/scaling is too fast? Too slow? 

More Resources on VP of Sales

Jason Lemkin of SaaStr is one of the best voices in our space when it comes to understanding the nuances of hiring sales leadership. 

In addition to our 32 questions above, you should check out Jason's 10 Great Questions to Ask a VP Sales During an Interview (it's actually 11 questions): 

Here are the questions from the video:

1.  How big a team do you think we need right now, given what you know?  

2.  What deal sizes have you sold to, on average and range? 

3.  Tell me about the teams you’ve directly managed, and how you built them. 

4.  What sales tools have you used and what works for you?  What hasn’t worked well?  

5.  Who do you know right now that would join you on our sales team?  

6.  How should sales and client success/management work together?  

7.  Tell me about deals you’ve lost to competitors.  

8.  How do you deal with FUD in the marketplace?  

9.  Do you work with sales engineers and sales support?  If so, what role do they need to play at this stage when capital is finite?

10.  What will my revenues look like 120 days after I hire you?  

11.  How should sales and marketing work together at our phase?  

You can follow Jason on LinkedIn, in addition to the YouTube channel above. 

Ready to Hire a VP of Sales?

Asking the right interview questions when hiring a VP of Sales is crucial. It allows you to assess their understanding of sales strategies, their ability to turn around a struggling team, and their skills in building and maintaining relationships. 

But, you've also got to ask yourself, "Am I setting this person up for success?".

A VP of Sales can be transformative to your team, but if you throw them into a chaotic mess or a situation with zero fundamentals in place....even a superstar will struggle.

Instead, it's much better to have your sales team "built" - at least to a basic level - before bringing in the VP of Sales. That way, they can simply take over the team and focus on scaling it while optimizing your processes. 

Use the questions in this article to evaluate your candidates and find the best fit for your team. If you have any other questions about developing your sales strategy and growing your sales,  schedule a free growth audit with Kyle here.

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