Max out either Recruiting or Game Management skill tree

Take your pick on which branch you want to max out with your dynasty coach. Id personally recommend Recruiting to help with your recruiting achievements, although game management will lead to Pop The Clutch. Make sure to set leveling options to fastest.

Another option is to use a pre-existing coach, at level 20, sim a season and then elect to reset your upgrades, and then reassign them in a way you see fit for this achievement.