I second what WMU said. It is a blast, I got lucky though. A DZ took a chance on me with 280TT and brought me on full time on two 182's and a 206. My best advice is to get to know the people at the DZ, most skydiving jobs are gotten through the buddy system. Just take care of the planes and they will take care of you.

Also, dont be pressured into doing something you dont want to do or feel safe to do, managers and DZO's may not be pilots and that cloud layer might look like 'industrial haze' to them. Watch the jumpers too, at least at my DZ, the guys would occasionally climb on the plane at altitude and one particular guy would pull on my aileron control cables during climb. Put them in their place as necessary. And... if you heard nothing I just said, remember this: Boobs for extra altitude. I saw more titties per weekend flying jumpers than you could at a strip club.