Hiring a VP of Sales? 2 Key Questions to Ask Yourself

Hiring the right VP of Sales is one of the most important decisions for a founder or a CEO to make. When you hire the right VP of Sales, you see your revenues expand in an accelerated, more predictable and scalable fashion. When you hire the wrong VP of Sales, the vision of scalable growth doesn’t materialize, your revenue projections go backwards and for some companies this costly mistake is a deadly blow to their business.

I have come to particularly value two key questions when recruiting a VP of Sales, based on my personal experience and the observation of many other companies.


1) What are the right reasons for hiring a VP Sales? 

Don’t hire a VP Sales to sell.

Many early stage founders or CEOs are the acting VP of Sales until the company gets some revenue traction and can afford a full-time VP of Sales. Often, the hope is that the new VP of Sales can sell better than the founder or the CEO, can close an increasing number of high-profile deals and scale revenue accordingly. I have been in those shoes and remember being impressed by the display of flagship transactions with marquee customers landed by prospective VPs of Sales.

Do not give in to the temptation of basing your hiring decision on that. I made that mistake. The result was that the VP of Sales would never be as good as me or the founder in selling the value proposition, and the high-profile wins we achieved still did not translate into a scalable process.

Hire a VP of Sales to build an amazing sales team and to manage it to maximize sales per lead.

The main responsibilities of a VP of Sales should be the following:

  • Recruit: building high performance sales teams
  • Assist: coaching and helping sales teams close deals
  • Set direction: defining the most appropriate sales strategy for the given solution
  • Help scale: establishing the right processes for a repeatable, scalable sales model

If you look at the most successful VP of Sales, you will see them excelling in the execution of each one of those tasks.


2) What type of VP of Sales do we need at this stage of our company? 

Do not hire a VP of Sales based on his/her résumé.

I have been in situations where the prospective VP of Sales was coming from companies that ‘made it’. Excitement was building up in our team based on the fact that the candidate from this big name company was even talking to us. We were envisioning the possibility of replicating that company’s revenue trajectory with this person on board. The candidate was impressed by our early successes, but never worked in a company at our stage and assumed that many of the things he was used at in terms of product maturity and sales support were already in place. It became obvious after a while that despite the impressive resume, we did not have a fit. The expectations, motivations and skills of the candidate were not in alignment with what our business needed at that stage of our development. We needed a builder, while he was thinking scale…

Hire the best fit for your stage.

After ensuring that you are hiring for the right reasons, it is imperative that you hire someone who is the best fit possible for the stage of development of your company. The skill set and motivations of VPs of Sales can vary greatly at the various stages.

  • $0-$1m in recurring revenues: what a company needs at this stage is an evangelist. 

Most companies at this stage do not need to hire a VP of Sales, because it is very unlikely that they will find someone who is better than the founder or the CEO at positioning the value proposition and making early adopters fall in love with it. The first sales reps should be evangelists too and report directly to the person acting as the VP of Sales. They are usually smart and technologically savvy, enamored with the space, and draw motivation by being able to influence and help shape the first product launches and sales approaches.

  • $1m-$10m: what a company needs at this stage is a builder.

The first VP Sales a company will want to hire is a hands-on candidate, capable of taking your first references and extrapolating assumptions of repeatability for the most important tasks, starting from recruiting and the sales process. This person, a true builder, likes developing repeatable processes, knows how to close deals and manage people, how to run lean and getting results with limited resources.

  • $10m-$50m: what a company needs at this stage is a grower.

Growers are good at optimizing and scaling processes that work. They know how to build larger teams and growth infrastructure based on proven characteristics and best sales practices, how to leverage growing budgets and resources and turn them into strong revenue growth. The best candidates are found in companies that just went through this stage and may have recently been acquired or gone public.

  • $50m-$100m+: the head of sales at this stage is a manager of managers.

As the game gets big, the head of sales is now managing sales via other managers and spends a lot of time setting expectations and managing upwards. This person thinks in aggregate terms and percentages when it comes to his team members, sales productivity and revenue. This person is also a very good presenter who knows how to run and present reports to his managers, his peers executives and the board of directors and how to secure budget for his team. Candidates from large companies tend to possess those skills.


In conclusion, resist the temptation to move quickly and go with the impressive resume. Spend the time to answer these two key questions. You will be more than rewarded with higher chances of success.

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