Is it possible for a very successful man to like a woman who is beneath his status and makes a lot less money than him?

It is definitely possible. It may be a conflict of interest if the woman works directly beneath him down the line and they are usually careful of that. Plus the whole matter of "sexual harrassment" gets in the way of them asking for a date. If the woman works for a different company, she is safer to date in his eyes. Show plenty of ambition, a man in an executive status likes to see that in a woman.