A printing system including a printer that sends a printed print medium to a post-processing machine is provided with: a job sorting unit that sorts a plurality of jobs into a plurality of groups; a required printing time calculation unit that calculates a required printing time per set required for printing for each job; a short job determination unit that determines, as a short job, a job for which the required printing time is shorter than a minimum processing time that is a minimum time required for processing for one set in the post-processing machine; and a job group generation unit that generates, on the basis of a plurality of jobs sorted into the same group, a job group obtained by grouping standard jobs (jobs not determined as short jobs) and a job group obtained by grouping short jobs.