When to Hire Your First Salesperson
Added 2026-11-06
Hiring a seller before the founder can sell just moves cost earlier.
I am considering my first sales hire: [business, how deals close now, price point, cash]. Decide: 1) confirm whether selling is already repeatable — who sells, cycle length, conversion; 2) list the preconditions for hiring and which missing one causes failure; 3) compute the cash cost and payback — base, commission, recruiting, training, management time; 4) separate "not enough selling hours" from product, pricing, or channel problems, with evidence; 5) give three ways to validate repeatability without hiring; 6) name the signal to hire immediately and the signals that say not yet.
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How to use
If the founder cannot sell it, a salesperson will only learn not to.
Try tweaking it
- Have it state how the hypothesis could be falsified before discussing execution.
- Split the plan into a one-week testable experiment.
What you should get
- A small testable experiment with a failure threshold
- Costs, risks, and what needs outside confirmation
Common mistakes
- Asking for a "full business plan" and getting unverifiable optimistic assumptions.
- No failure threshold, so you never know whether to continue.
How to check the output
- There is a clear failure threshold, testable within a week.
- Costs, assumptions and risks are listed separately.
Where it works
- Good for: turning business assumptions into a small testable experiment with a failure threshold first.
- Watch out: for pricing, contracts and legal points, treat output as a draft needing professional review.