After graduating with degree in history, Riley began his coaching career at The Albany Academy, leading the program while also serving as a scout for the Charlottetown Islanders, a team in the QMJHL.
In 2017 he returned to college hockey, becoming the first head coach for Wilkes University, and had a full year to prepare for its inaugural season in 2018–19.
When Wilkes hit the ice, the team performed well, finished in a tie for 3rd in the UCHC, but lost their quarterfinal game in the conference tournament.
After just one season with Wilkes, Riley was hired as an assistant coach by Colgate, working under one of the most respected men in Division I hockey, Don Vaughan.
Riley's tenure with the team saw the Raiders achieve moderate gains, rising from 10th in ECAC Hockey to 8th and won its first playoff round in five years.