Business managers should try playing Tropico games sometime. Penultimo mentions in a tutorial popup, the first time a critical building--such as a teamster's office--lacks workers, that perhaps you should increase the wage for this type of worker, Presidente (or increase immigration, or pay to import a foreign specialist).

He never suggests that the job should be offshored, because that would be bad for Tropico's economy, and he's a Tropican loyalist.

For some reason, you can't force a Tropican citizen to cycle between multiple part-time, low-paying jobs to take advantage of fractional-employee building capacity. Perhaps they are programmed to not like that. Can't imagine why.~