This is absolutely one of the hardest hires to make—a good head of sales will dramatically accelerate the revenue trajectory of the company, and a bad head of sales will significantly slow your growth. So it’s definitely a high-stakes hire.
The question I’d probably ask is: is your playbook mature enough that you think you can hand it to someone and have them run with it & scale it up? Or are you constantly iterating on it?
If you’re still constantly making tweaks, what you may want is a sales manager to manage all of your sales reps, but you probably still need to stay close to the machine.