It's tough because the need changes over time too. On day 1 you need someone very technical who knows how to sell to early adopters. (Zenefits did this ok) La

It's tough because the need changes over time too. On day 1 you need someone very technical who knows how to sell to early adopters. (Zenefits did this ok) Later on you need people better at getting to the early majority. (Generally it's by tackling one industry vertical well [0]) The head of Sales for the former may not be right for the latter. Two thoughts... 1 - The incentives you choose matter a lot in both attracting and maintaining sales people. 2 - Look to people who you have bought from that you think would fit in their culture. Call them and ask, "Do you know anyone similar to you?" Since you're an early adopter too, they are the right target. And they may volunteer themselves. 3 - You have to balance potentially long sales cycles (it takes a year to build up a pipeline) with being able to pull the trigger when you get the hire wrong. There are a lot more mishires in Sales than most other areas. Good luck! [0] https://en.wikipedia.org/wiki/Crossing_the_Chasm https://en.wikipedia.org/wiki/Crossing_the_Chasm