I think I'd apply for the position of guy who's super interested in something that's only interesting cause it's gsmeplay relevant. I'd stand by a river staring at it day and night and when the protagonist talks to me I'd say "I'd bet I could use a boat to cross this river."
I wanna say Gambler but then they'd change me to "G*mer" in later gens so idk lemme think about it
That was my second option