12 interview questions to ask a VP of Sales

This blog reveals the top 12 VP of Sales interview questions to ensure you make the right hire for your start-up.

As a Founder, hiring your first VP of Sales means more than investment in your sales operations. You're selecting the individual who will lead your business through an incredibly important growth period.

There's a lot of pressure to get it right. Hiring the wrong person could mean your start-up misses it’s window of opportunity. Or worse, doesn’t get the funding you need to grow. So, how do you ensure you're hiring the right VP of Sales to lead your start-up?

Having worked with a number of exciting start-ups to hire their VP Sales, Nick Guy, has run hundreds of interview processes for this important hire. Here are his recommendations for interview questions.

1. Who are you bringing with you?

Your VP will be building a sales department. It can be a good idea to assess whether you can leverage their network.

2. How do you see your relationship with other areas of the business?

It's essential that your sales leader is collaborative and comfortable communicating with different teams. As sales is often the first to receive client feedback, they have unique access to your customers. Your VP of Sales must be willing to proactively share information with different teams to ensure successful business growth.

3. What are you most proud of in your career? 

This question will allow you to understand how they personally see success. Then you can assess whether that aligns with your business strategy and core company values.

4. What's your sales process and philosophy? 

With this question you can delve into how they define success when building a team. It helps you understand what they'll look for in new sales hires and how they'll measure sales performance.

5. Who is the best boss you've had, and why? 

Asking this question lets you know how they personally like to be managed. This gives insight into what your relationship will look like if they were to join the business.

6. At what point would you hire team members? What roles would they be, and why?

Picking the wrong time or approach to recruitment can be fatal to a start-up’s growth. This question shows whether you will align on expansion plans.

7. What do you think the compensation package for your sales team should be, and why?

By understanding their opinion on salaries, you'll learn the market they will be hiring in.

8. What is the hardest obstacle you have overcome as a leader?

There are inevitable obstacles that come with sales leadership. Understanding what they perceive to be big obstacles, how they deal with them and the outcome, gives an understanding of their crisis-management processes.

9. Why did you become a leader? What keeps you in the role?

This is an excellent question for any interview. Understanding a person's “Why” goes a long way in understanding how – and if – they will work for your business.

10. How do you successfully retain the best sales people?

Understanding how your new sales leader will tackle churn and retention is critical. According to research from RAIN Group, it takes 15 months for a sales rep to become a top performer. To ensure your sales team are performing at their best, it's important to ensure you're retaining your team.

11. Why do you want to work in a start-up?

This one is particularly important if you are interviewing people with limited start-up experience. Working at a start-up is not the same as at a large corporation. Knowing their mindset can help you decide if it's the right place for them.

12. Ask them to pitch or demo

You might think that this isn’t a necessary stage because they’re not selling themselves. However, your VP of Sales will be coaching and training your team to do this, so you should assess their abilities.

Here are some ideas of what you can ask to see:

• Run through a discovery presentation
• Examples of previous sales playbooks
• 30/60/90 day plan of their GTM strategy

Searching for more interview tips?

Ultimately, to hire a great Vice President of Sales, it’s important that the whole interview process is methodical. You should be patient and _ to ensure you find the right sales leader for your start-up.

You could always add many more things to the VP of Sales hiring process. This is by no means an exhaustive list. However, these key questions go a long way in helping to devise a recruitment process. Plus, they absolutely work when nailing down who to ultimately hire and, most importantly, who NOT to hire. 

If you’re looking to hire a sales leader and are struggling to find the right fit, get in touch with Nick Guy. He would be happy to share his experiences in supporting early stage start-ups with this all important hire.