I have a theory that his father’s as much a salesman of surgical supplies as Al Capone was of used furniture. He’s too well spoken and quick with a cane and heel, especially for an old man, to be in sales. I think he’s retired intelligence or [whatever the English native version of the] Mafia and surgical supplies was his cover. And of course a compleat bastard.
Regarding Roger: he’s less than rich but more than mid-level manager. His English bosses trusted him to be their regent at megamillion dollar accounts (not just the ad agency but the place in India where they were sending him), so he probably earned well over $50K per year plus bonuses while working for them.