Bursts of Color - Hiring a VP of Sales
The title VP of Sales typically refers to a company's revenue leader... though that can mean anything from an individual contributor to a senior executive responsible for a 500-person team. So when a founder says they're ready to hire a VP of Sales, the first question is: what level of seniority to you mean?
Using This Table
The table above is meant to provide a rough framework for what level of sales leader to bring in when. Starting with the first row: in the early days of selling, it's often best for a founder to lead the sales effort personally, so she can learn and tweak things in real time. By the time your team has 5-10 salespeople with some level of consistent performance, it's probably time to hire or promote a Head of Sales, who has experience with a team this size. Of course, these columns are illustrative and the real world will differ. The key thing is to hire someone who has been successful at the the team size you'll have for the next year (i.e., don't hire way above or below your current need).
Left Brain vs Right Brain - Optimize for One
I find that most revenue leaders excel at either:
"Right brain" people-oriented stuff like courting clients and hiring & motivating sales reps. These leaders were usually excellent salespeople themselves early in their careers.
"Left brain" process and analytical stuff like planning, pricing, packaging, commission and territories. These folks often started their careers outside of sales -- say in ops or analytics.
Very few people are excellent on both of these dimensions, so I suggest deciding up-front which one is most important. Ideally, your new leader will complement an existing teammate... so you can set them both up for success.
Other Key Considerations
Company Stage Fit. Being successful at Facebook in 2021 is amazing, but is poor training for a 30 person startup. Hire someone who has experience working at a company your size.
Price Point Fit. Selling $500k deals is terrible practice for selling $5k deals, and vice versa. Find someone who has been successful selling products in your price range.
Don't Overweight the Interviews. These candidates are all charismatic! Focus on objective measures and references.