Answer: Hire your first salesperson when you, the founder, have closed repeatable deals with a clear customer profile, you can write down how you sell, and there's enough pipeline (or a proven channel) to keep a rep busy. For most B2B startups under €5M ARR that comes after roughly 10–20 customers (a rule of thumb, not a hard threshold) and once the founder's selling time is clearly limiting growth.
A hands-on Account Executive with early-stage experience. Hire two if you can, so you can compare them. Don't hire a full-time VP of Sales yet. A fractional VP of Sales can build the process and hire the reps first.
By Matteo Papaluca, Fractional VP of Sales at Inscaler. 15 years in B2B sales, hundreds of salespeople hired, 200+ startups helped.