A vice president of sales is arguably the most important and expensive executive hire.

Let’s assume you have several candidates who have a long-term track record of success in sales and sales management. You hire one of them, and a year later they are barely getting traction.

What might you have done to better align the hire with your organization? Here are six factors to evaluate:

1. Product complexity. It’s not enough to hire a successful sales leader from within your industry. Just as important is whether the product has similar complexity. For example, if you sell complex machinery and your candidate has a history of selling widgets to the same industry, they will be ill-equipped to express your value proposition.

2. Going to market. Some firms depend on hunters to bring in new client “logos.” Others are primarily account management. Still others depend on channel partners. It is critical to align your new VP of sales’ skill set with how you go to market and not assume they will adjust. They won’t — they will try to do what worked for them in the past, whether or not it fits your business model.

3. Fit of the Rolodex. Nothing is more impressive than an extensive file of contacts in your industry. But have they sold to the same level of decisionmakers? An individual can have a great Rolodex that doesn’t really overlap with the decisionmakers for your sale. They might have been selling into IT vs. business units, or middle management vs. the C suite.

4. Fit of culture. Is your organization ready to support a successful VP of sales? I know smaller organizations that have never successfully hired a lead salesperson. In these companies, one of the founders has always been the key rainmaker. They don’t have the organizational infrastructure to support a successful sales leader (or sales force); most of that critical information is in the founder’s head.

5. Can they sell for a company without a famous brand? If their primary success has been with a name-brand provider (i.e. GE or IBM), how will they adjust to selling a firm their prospect hasn’t heard of before? If you sell for a company that has its own golf tournament, you don’t have to work hard to get a meeting — you are always on their shortlist. Often sales leaders from name-brand organizations do better on their second stop after leaving the mother ship, once they have made the needed adjustments.

6. Size of team. It is often considered a coup to land a sales exec from an industry leader. But if your candidate was managing a regional team of 40 reps, and you have eight reps in your entire company, recognize that the person spent much of their time “managing out of a spreadsheet” while you need a “player-coach” who can sell and manage a small team in the field. The fact that the candidate did what you need 10 years ago doesn’t mean they are a good fit to do it now.


Isaac Cheifetz is an executive recruiter and strategic résumé consultant based in the Twin Cities. His website is catalytic1.com.