Jason M. Lemkin explains why fast-growing sales companies struggle to promote talent: they hire so much external talent that internal promotion slots disappear. He argues the biggest failure for future VPs of Sales is never learning to hire. At Outreach, he gave salespeople a clear path from SDR to AE to manager, letting them practice recruiting 2-3 reps with guidance. Riley Devine, the top AE for four straight years, proved the model works.
Chapters
There's actually some irony. Sometimes it's easier in a slow-moving organization because you don't hire as much. And so you can actually almost promote anyone good. The irony is the faster you're growing, you're bringing in so much human capital, you can't promote every SDR to AE and every AE to director, but you got to try. And I think that's what Brendan and Sam, the rest of the team did over the years, even when I wasn't there, is give everyone a chance to get promoted for real and then build a team and hire a team. So everyone got their shot in a comfortable environment where they knew the boss and they could get promoted as an IC and then they could manage a few folks and then they could hire, learn how to hire 2 to 3 folks with some help and not screw it up, right? Because that's where you, that's where almost everyone fails on the way to a true VP of sales is they never learned to hire. They never learned to hire and they're a great IC and then maybe if they're in a bigger company, maybe at ZoomInfo, I don't know, maybe if you go to director, you mostly inherit a team, right, a lot of times, right? You don't actually show up and they're like, you know, you gotta go hire 10 AEs, you actually, You hire 8 and then like the team brings in 1 or 2. So you actually don't, I'm not, a bigger company, you don't always learn recruiting tools. And so, but if you don't figure that out, you'll stumble, right? As soon as you get a leadership role. But I think they had the runway to do all this over 4 years and it gave everyone a chance to do it in a sheltered way and learn. And I think they flew. And I remember one of these guys on our team that, was one of our top 5 guys. And then for 4 years, he was the number 1 AE at outreach. Number 1 from the day he started. What's his name? What's that? Riley Devine. Yep. And I was like, I met him. I'm like, Brendan Sky, I don't know. I don't, I don't get it. Like he worked from home in shorts. Like now that's normal. I didn't get it, but just gave the folks room to run and be the diverse. And that, that's the key. Right. And so, but you got to have, But I think giving folks a chance to run and just promoting everyone you can, as hard as it is, there's not enough room on the org chart, but the ambitious want to be promoted in sales, right?
