IMO, the problem is that the ones that approve the look-and-feel aren't exactly the users, but the hirers. And since they already live inside the company, some things might make sense to them, and not the wider public.
Yeah precisely. The CEO can connect the dots, so they don't stop to think if a customer could connect the dots, or if anyone would bother to think that hard (about their cryptic site, which is 7th website of 10, in a row of browser tabs).