When interviewing a VP of Sales, it’s essential to ask insightful questions that uncover their experience, expertise, and strategic mindset. Here are 5 questions that will help you do that:

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

This question evaluates the candidate’s strategic thinking and ability to analyze data and make informed decisions regarding team size and resource allocation. For example, if your company has an annual revenue of $2 million and wants to grow it to $6 million, the candidate should be able to calculate the number of team members and resources needed to scale it, even if it’s not entirely accurate. The question also gauges their ability to optimize resources and operate within budget constraints. A strong candidate might analyze revenue projections, assess sales team productivity, and propose a scalable team structure to achieve growth targets. They may emphasize the importance of cost efficiency and the ability to achieve results with limited resources. Being frugal with costs is very important for effective management.

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

Understanding the candidate’s experience with various deal sizes provides insights into their adaptability and effectiveness in different sales scenarios. You should make sure to understand what deal sizes the candidate sold and stick to semi-similar deal sizes. For example, if the candidate sold $5k to $10k deal sizes and you want him to sell $200k deals, the candidate will probably struggle since the sales cycle will be too slow. Ideally, you should hire a VP who has sold similar deal sizes because the experience between selling SMBs and selling enterprises is very different.

3. How many teams have you directly managed, and how did you build them?

This question assesses the candidate’s leadership style, experience in team development, and ability to foster a high-performance culture. It also provides insights into their approach to recruitment and training of the sales team. The VP must hire and onboard the reps himself. For example, if a VP comes from managing a sales team of 50 reps and you’re trying to get him to manage 5 reps, that’s probably not gonna work. Hire a VP who has experience managing 10 to 20 reps which is a similar space. 

4. What sales tools have you used? What has been effective, and what has not? 

This question evaluates the candidate’s familiarity with sales technology and their ability to leverage tools for improved sales effectiveness. You need to make sure that your VP knows which tools are needed and which are not. This will make it easier for the VP to get running because he will have insights into the most efficient and cheapest tools in the market. Otherwise, the entire process will go much slower. Thus, it is important to have a VP who knows which tools are needed and how to use them so that he can teach the team and improve productivity.

5. How do you believe the sales and marketing teams need to work together? 

This question assesses the candidate’s understanding of the relationship between sales and marketing and their ability to facilitate collaboration between the two functions. The VP should understand marketing and lead generation so he can know how much to rely on marketing and execute his own program for outbound sales. So this way, he can understand how marketing will help and what else he can do to supplement marketing. This is an important skill because the VP might completely depend on marketing and not have a proper outbound program to get his own leads otherwise.