Well, with my own core experience in senior sales hires and having discussed this with a number of clients, I wanted to share the top tips and questions to ask during the hiring process to ensure you hire a great VP of Sales.

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1. Who are they going to bring with them? They’ll be building a team so it’s important you can leverage their network.

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2. Get them to pitch or demo. You might think that because they’re not actually selling that this isn’t important but they’ll be coaching and training people to do this so it should be at the standard you require.

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3. How do they see their relationship with other areas of the business?Marketing, Product etc. This communication is essential if they – and your sales team are going to be successful. Do they take a collaborative approach? As sales is often the first line of initial client feedback, it is important any sales leader ensures this is fed back to the other areas of the business.

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4. What are the 3 things they’re most proud of in their sales career? This will help you understand what they personally see as a success, and whether that aligns with your business strategy and core company values.

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5. What is their sales philosophy and methodology? How do they define their approach to success when growing a team?

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6. Who was the best boss they have had and why? This will give you an idea of how they personally like to be managed and the effect that may have on your relationship if they were to join the business.

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7. At what point would they look to hire more resources? What would they be, and why? Your VP of Sales – or sales leader - will be in control of hiring, so it is essential that you know how they look to grow the team. Picking the wrong time, or approach to hiring can be fatal to a startup’s growth.

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8. What do they think the compensation package for their sales team should be?And why? It’s important that they understand the market they will be hiring in.

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9. What is the hardest obstacle they have had to overcome as a leader? And how did they deal with it? What was the outcome? This will give you an understanding of their crisis-management processes and how they deal with the inevitable obstacles that come with sales leadership.

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10. Why did they become a leader? What keeps them in this role? This is actually a question I ask my own clients when taking on a new role. Understanding people’s “Why” goes a long way in understanding how – and if – they will work for your business.

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11. How do they successfully managed to retain their best sales people?Understanding how your new sales leader will tackle churn and retention is important, particularly as it takes on average 42 days to fill an open position. That is 42 days that sales seat is not selling, and that can be hugely detrimental to a startup’s success.

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12. Finally, ask them “Why Startups?”. It is important to understand particularly important to understand this if you are hiring people who have limited startup experience.

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Ultimately, to hire a great VP of Sales or sales leader, it’s important that the whole process - not just the questioning - is methodical and that you are patient enough to find the right person. And if you’re looking to hire a sales leader and are struggling to find the right fit, I’d be happy to share my experiences and the startups I’ve personally helped; nick.guy@finlayjames.com | +1415 638 7817

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