Would work pretty much like a bicycle courier.
Have a bike... edgy clothes... big stupid mail bag over the shoulder.
BIKE SHOES.
Looks like a courier...
Actual job? ASS KICKER.
"Hello, Corto's Ass Kickers."
"Hi... I need a delivery to 1220 Main, Suite 1500"
"We can do that... time?"
"Has the be there before 2:00"
"No problemo... Kickee Name?"
"Joe Blow"
"Righto... Malicious?"
"Totally... make it leave a mark!"
"Deal... Credit card number..."