The ideal flow is:
- You (founder-CEO) close the first batch of customers, say the first 10 or 20. If you don’t, you’ll never really know how it’s done. Or be able to help anyone else, really.
- Then, once you know how to do it yourself, you hire 2 sales reps. Not just 1, or you won’t know why they do well, or don’t. You need to run an A/B test. More on that here: When You Hire Your First Sales Rep — Just Make Sure You Hire Two | SaaStr
- After you have 2 reps hitting quota, you hire a head of sales. This is generally after $1m-$2m in ARR. Because then their #1 job is hiring reps 3–300, and getting them to hit quota. But if your hire the VP of Sales before that, you are asking them to figure out product-market fit. Not to accelerate an engine that’s working, albeit at a very small scale.
Sometimes, you can get away with hiring a great head of sales as your first sales hire — especially if you have a freemium product that already has revenue going. Or if the CEO has gotten the company pretty far (say that same $1m-$2m ARR).
But most heads of sales will do better if there are already a few reps proving it can be done. Then, their job is to do it better, again and again. And again.
A related post here: Should Your VP Sales Start Off as a Player-Coach? | SaaStr