For #1 I like the fact that he looks friendly and approchable but there's a sense of mystery. However, this version looks too much like a park ranger child molester- We want more of a DETERMINED UNSTOPPABLE FORCE vibe, like Robert Patrick in Terminator 2, but with insurance quotes instead of time travel and the enslavement of the human race by machines.
For #2 This to me looks like Mr. QuoteFace BEFORE he was hit by the meteor fragment (he didn't wear capes before though) maybe like this guy if now he had dreadlocks and a beard and a flamethrower-style insurance quoting cannon. I like the briefcase and tie though- those are nice touches. Maybe some sort of insurance machette?