I'm thinking of some sort of counter terrorism analyst position... which is a nice way of saying "well-payed hacker". Think of Chloe O'Brian's job from 24. As for the other character, perhaps a bar owner. Think of Quark from Deep Space Nine.

Obviously these two chars aren't cookie-cutters of those. I'm just giving you something to go by as to what their jobs entail. The actual personalities of the examples are irrelevant. I find both annoying. XD

On the other hand, an annoying character would be an interesting element. The character you love to hate... Not saying I'll do that. It would be a challenge as I typically create characters I actually like. Creating something I hate would make writing a bit hard.