Bryan from Entrepid here. We disagree with the advice of hiring a head of sales as your first sales hire. You are better off finding a someone with 3-6 years of experience to be the first hire as an IC. This hire (and maybe a few others) will help you grow the company to a point where you can attract a badass VP of sales / head of sales

This all depends on the capabilities of the current exec team. Generally my experience has been:

Exec team with mature sales presence/leadership = hire less experienced (3-6 years).

Exec team with immature sales presence/leadership = hire more experienced (6-10 years with opp to become a VP of Sales).

Good guide - thanks for putting together.