I do think it’s tough.
Many employers will be skeptical you really want the job — versus just needing one. They’ll be skeptical you can still be a role player and implement someone else’s vision. They’ll be skeptical you will stick around.
However … look at most successful start-ups and tech companies. You’ll see ex-CEOs in their leadership teams all the time. See David Marcus at Facebook, for example. He made tons of money at Zong and Paypal, and still after that, headed up Facebook Messenger on a strong run.
So it works, and when it does work — it works really well. Having a right-hand person that has truly done it before, and that can be a “the CEO of a division” or a group can be truly empowering for a CEO to hire.
So how do find someone that can see this, and take a risk on you? The trick I’ve usually found is go back to the CEOs that you’ve gotten to know well over the past 5 years as a CEO yourself — and talk to them. Be very frank and transparent. One of them will likely offer you a role. Every CEO of a fast-growing startup or company needs a few seasoned veterans to help them. Take that as your next role, at least as your transition role.
