The first VP of Sales is the most consequential hire a Series A company makes. It is also the most common hire that does not work. Across the eleven active companies in our growth funds, the first VP of Sales has worked out in seven and not worked out in four. The seven that worked have a few things in common.
The first is that the hire came after the founder had personally closed the first fifteen customers, not before. A VP of Sales cannot build a sales motion for a product the founder has not sold themselves. If the founder has not done the work, the hire is a delegation of work that has not been defined.
The second is that the hire came from a company one stage ahead, not three stages ahead. A VP of Sales from a public software company is usually the wrong hire for a Series A. The systems, the cycle, and the deal size are all different. The right hire has built a sales motion at a company that was Series B when they joined and Series C when they left.
The third is that the hire was given a quota, a territory, and a quarterly review cadence in their first thirty days. The wrong pattern is to give the hire six months to learn the product. The right pattern is to give them thirty days to learn the product and a quota on day thirty-one.
The fourth is that the founder stopped selling on the day the hire started. The most common failure mode is for the founder to keep closing deals alongside the new VP of Sales. The new hire never owns the pipeline, the founders never build the management muscle, and the company never scales beyond founder sales.
We use this rubric before we approve a VP of Sales hire at any portfolio company. It does not guarantee the hire works. It does improve the odds.