Q:  I’m Head of Product and I think our CEO is actively recruiting a VP of Product. What should I do?

  • First, usually, just go talk to your CEO. It’s totally fine to do that. You just … don’t know.  If she/he is the type of CEO you really want to work for, you should be able to have an open conversation here, and get a mostly open answer.  Yes, it might have been nice if the CEO had talked to you first. But it’s fine if you go first.

Then, a few additional thoughts and learnings:

  • If you are potentially being “topped”, be a bit Zen about it. Don’t see it as a threat. It may mean you need to find another role, or another start-up at some point. But not today, and not necessarily. It may be deeply disappointing to find out the CEO thinks she or he needs someone “above” you on the org chart. But that’s probably also a sign you’ve done some things well to get the company to where it is today.
  • Understand most CEOs often don’t handle this well themselves. It’s complicated. When you think someone may have reached their limits, when do you tell them? Do you involve them in the search? How early? Just understand it may be awkward for your CEO, especially if she/he wants you to stay. So don’t take it too personally if you feel like you haven’t been kept enough in the loop.
  • There are many good reasons to stay at least a little while longer, if you are getting a new boss. Maybe he’ll be terrible. But they might be great. You might learn some things from him or her, even if you don’t stay forever. It’s almost always worth it to be a good sport and just see what happens.
  • Being part of the interview process for your boss is good to do once. You will learn a lot. It’s a surreal process and you’ll learn so much being on the “other side” of helping to hire your boss.
  • Be self-aware, and honest.  Have your metrics plateaued?  Have bookings flattened?  Are leads not growing anymore?  Are you struggling to ship more features?  If so, that doesn’t mean you aren’t great, and don’t do great things.  But it may mean you need to get to the next level.  Most of us do.
  • There may not be someone better than you — even if a search gets kicked off. It’s often a learning experience.  It can be awkward.  But often, you ended up re-interviewing for the VP role.  And you might win it.

So it’s hard not to take some of this personally. But just go to your CEO, be respectful — and just ask.

If you are a stretch “Head of” or VP, you should be regularly having this discussion with your CEO anyway.

And a final note, I just caught up with two old members of our Adobe Sign team who had a boss brought in over them.  Both are still VPs at their startups today, at super unicorns.  They stayed zen, and they stayed, and it worked.  They’re basically still running the place, with the same or better titles, and were able to scale far further because of it.  They just got a seasoned CXO above them to help them run even further.

(note: an updated SaaStr Classic answer)

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