You're looking, it seems from your desciption for a decision making tree, right?
What factor(s) determine(s) who gets a job, right?
Sounds like:
Determine the job type,
Find all guys who can do that job type.
Find the guy with the fewest number of active jobs.
If all have an equal number of jobs, find the guy whose previous assignment is older than everybody else's previous assignment.
Something like that??