Probabaly the best and easiest way to get a start droping skydivers is to become one yourself. Choose a school that operates piston aircraft and trains AFF. Turn up and fit in. Skydive training operations are fun, a great way to meet people and always seem to have a party atmosphere. Social activities continue long after the last jump.
Wen a vacancy happens the bloke on the spot will get the gig, and having already jumped you will know all about it.