Jason M. Lemkin warns against hiring a sales leader without hiring experience. He uses Bill from Drata as an example of how random recruiter hires lead to mediocre reps and collapse. Instead, find someone ambitious who has already hired at least two quota-hitting reps.
Bill comes over from Drata, the number one rep, and Bill doesn't know who to hire. And Bill tries to hire the other folks at Drata, but Drata, they would want to leave Drata. And Bill doesn't know how to hire. Bill's never hired a quota carrying rep and Bill can't find anybody. And 30 days go by and it's bad. And so Bill hires a random recruiter and Bill starts bringing in random people because he doesn't. Because he doesn't have a network to pull from and he doesn't have people to bring in and he doesn't know. And the random recruiter gives them the really mediocre candidates and they don't really want to work for Bill because he's never done this before and he's not that polished. And you start hiring C reps into it and then everything spirals and falls apart. Okay, so the ideal stretch head of sales, the ideal one is they're ambitious, they get it, you believe in them, but they have to have hired a couple people that hit quota. 2. If they've hired two, you can run the risk that they will hire 100 for you. They can reproduce that experience.
