I know one guy who used to work on the ramp, he's now a 737-800 Captain.
I worked as a night ops assistant, now fly bizjets.
How long did it take to get the CPL+IR isn't quite relevant as I converted an Australian ATPL to a JAA one.
Don't expect to get a flying job directly because you've worked on the ramp but contacts are every thing. (Also, good flying passes etc when you're low houred)