have you actually looked into the jet option?? If the boss is so keen, why not go and speak to CASA and get some facts. The small crustations are aimed at single pilot/private use so are well within the reach of a CPL with a bit of experience. Get an "approved" training course withthe purchase and perhaps some supervisory CandT from an existing operator and you could well be there. Could be more cost efective than outgrowing a piston twin then outgrowing a turboprop then looking at the jet.....
Having operated both types, I know which is simpler. No 1"/1000/minute or cowl flaps and it's pretty hard to shock cool a PW engine.
just a thought.