If you're not flying it in passenger revenue service, I believe the requirements get a lot fuzzier - I would expect you'd need at a minimum a commercial multiengine cert to get rated for airliners, but I don't know that you actually need the ATP, unless you're going to fly in revenue service.
And, tbh, I don't care if the CEO of Boeing can take one around the pattern on their own. If they need a rated instructor with them to go fly one legally, so be it. Doesn't bother me in the slightest.
But I stand by my statement that the CEO should be able to understand airplanes and fly them reasonably competently, if they're the CEO of a company that builds airplanes. I don't mean "press release of them flying it straight and level on autopilot" - but to actually be able to get it competently around the sky in manual flight modes.
I consider the financialization (turning into loan servicers and financial service providers as their main stream of income) of "every company who used to build things" to be one of the worst things that's happened to American industry as a whole.