Founders ask 'when should I hire a salesperson' as if it's a timing question. It's actually a readiness question, and most founders check the wrong boxes before pulling the trigger.
The signals that feel right but aren't
Being tired of selling is not a hiring signal, it's a burnout signal, and it produces a rushed hire. Board pressure is not a hiring signal either, it's someone else's discomfort with your time allocation. Headcount targets in a fundraising deck are the weakest signal of all: a plan written months ago knows nothing about whether your sales process is actually repeatable today.
The signal that actually matters
Hire when three things are simultaneously true: you have personally closed 15 to 20 deals, you can write down the repeatable steps that led to each win without hand-waving, and your pipeline has grown larger than you can personally run without dropping calls or slowing responses. Any one of those alone is not enough. All three together means the bottleneck has genuinely shifted from 'do we have a process' to 'do we have enough hands.'
What to hand off first
Do not hand off the whole funnel at once. Start by handing off the stage you personally find least differentiating, usually top-of-funnel outreach and initial qualifying calls, while you keep running the later-stage discovery and closing conversations yourself for another few months. This protects the part of the process where your founder credibility still matters most, while freeing your time on the part that scales fine without you.
The handoff document that makes or breaks the hire
Before day one, write down: your best discovery questions and why each one works, your three most common objections and your actual response to each, the moments in a call where deals tend to stall, and the profile of the last five deals you lost, with the real reason each one didn't close. A new hire without this document is solving a puzzle with no picture on the box. Most failed first sales hires are not a people problem. They are a documentation problem wearing a hiring costume.
What stays with you even after you hire
Keep taking a handful of calls yourself even after your first sales hire is ramped. Losing all direct contact with buyers is how founders lose the market feedback loop that made the product good in the first place. Hand off volume. Don't hand off all your listening.