I report to a CTO and certainly can point to people who are more like this, but even the most agreeable still pushes back sometimes. If you understand how CTOs think and what they want/need, it's not someone to poke holes in their plans, but propose adjustments and alternatives that fill the holes you see. It's almost like good improv

Also CTOs (especially in supposed F500 companies like presented here) don't typically drive the project execution and interact with the development team in a more than cursory basis. THis is another reason I'm super-skeptical of the entire story. The smallest company on the current list is over 16K employees.