Not when you are tired of selling. When you can predict it. The honest test is whether you can write down who buys, what makes them buy now, the three objections you always get, and roughly how long a deal takes, and then have that be true for the next five deals. Most founders get there somewhere between 10 and 30 closed customers, and Jason Lemkin's line is that you should have done it yourself first or you will not be able to tell a good rep from a bad one. If you hire before the pattern exists, you are paying someone to discover your product market fit, which is your job, not theirs.
5 resources, 5 link-checked.
Two hours covering when to hire the first rep, what to look for, when to bring in a VP of Sales, and how comp and quotas should be set, all in one place. If you only watch one thing on sales hiring, watch this.
On Lenny's Podcast by Lenny Rachitsky and Jason Lemkin 2 hr watch
Ten specific, named mistakes rather than principles, including hiring a VP of Sales too early and letting a bad rep linger past one sales cycle. It is the fastest way to avoid the errors almost every first-time founder makes.
On SaaStr by Jason Lemkin 30 min listen
Open saastr.com →Kazanjy wrote the book most first sales hires are trained on, and here he is specific about the signals that say you are ready to stop selling every deal yourself. He also names what a founder must be able to repeat before handing it over.
On Lenny's Podcast by Pete Kazanjy 61 min
Names the two ways founders get the timing wrong, scaling too early and scaling too late, and walks the progression from founder selling to pods to a real team. Useful precisely when you are deciding whether it is time.
From Founding Sales by Peter Kazanjy 35 min read
Stripe's Chief Business Officer on building a written sales operating model (leads, conversion, deal size, win rate, cycle) so you can diagnose whether a miss is the rep or the model. The missing step in most handoffs.
From SignalFire by Sadasia McCutchen with Jeanne DeWitt Grosser 14 min read
How hiring and ramping gtm people reads from a different seat.
The same ground, over in Co-founders, team & legal, our Starting Up track.
