Jason M. Lemkin on when to hire a boss above a stretch VP: wait longer than you think, because most VPs go further than expected. If you do hire above them, keep them in the company and involve them in the process so you don't lose what they know.
I wanted to spend just a couple minutes talking about a tough topic with no perfect answers, but maybe a few insights, which is, what do you do when the time comes to top a vp? To hire someone above her? When you realize a VP that got you to 1 or 3 or 10 million isn't quite enough to get to the next level, it's impossible to sequence this, right? It's impossible to go out and hire someone else and keep the current person perfectly happy. But I've learned a few things. First, if you do this too early, you almost always lose momentum. If you go out and hire someone's boss when it's just getting good, almost always the business plateaus too early. And the second thing is, conversely, if you do it too late, you hit a wall, you stop scaling, and growth slows down. So what I do know is if it's imperfect, when in doubt, wait longer. Because if you're going to hit some sort of slowdown, you might as well hit it in a few quarters rather than hit it today. So what can you do? First of all, as we talked about, when in doubt, wait longer. When in doubt, see how far a stretch VP can go. Because worst case, you can push off that plateau a quarter or two. The second is when you decide it's time to top a vp. Do whatever you can to keep the current person at the company letterkeeper title. Hire a CRO or a CMO above a vp. The simple reason and for nothing else. When you lose that knowledge base, you'll lose so much momentum there too. Usually your VPs are the folks that know the most about the quirks of your product, your sales processes, marketing, whatever. Don't let that go out the door. And last, transparency is always tough when you're a topping person. But what I do know is you have to involve them in the process. Bring them into it when you're ready to top them, explain to them why. They may not agree, but it's much better than trying to do something stealthy behind someone's back. At the end of the day, 95% of your VPs aren't going to take you to 100 million. But I will tell you often, they can go further than you think. So give them a chance to at least defer the time when you stall out in that transition between the next VP.
