The most successful tech companies are typically led by their technical, product-oriented founder-CEOs who have very little experience in building a sales organization. Bringing on a sales leader and building a sales organization exercises a completely different muscle for most engineering-heavy startups.
And if you’ve hired right, managing a vice president of sales is meant to be tough work. That’s because the very best sales leaders are extremely demanding. They call out competitive weaknesses, constantly push for more feature velocity, and promise bug fixes or features that get crammed into every release. They stretch everyone to their limit. It will drive you and others in the company bananas.
But if your VP of sales is not periodically at odds with the VPs of product, engineering, operations, finance, etc., then he or she is probably not demanding enough. If done right, this role gives the entire company a reason to work harder as the sales VP reveals and strongly advocates for the customer struggle. That said, the CEO still needs to manage this person tightly. Because once the VP of sales unleashes her or his superpower — being a master negotiator/influencer — inside the company, it can create dysfunction across the team.