Entering his 17th season with Portland in 2022-23, Cronin joined the team as a basketball operations intern in 2006. In 2010 he was promoted to pro scout/salary cap analyst where he was a crucial part of the player evaluation and roster construction process. In 2014, he was named the team’s director of player personnel and in 2021, was named assistant general manager. As a result of his continued dedication to the team, Cronin was the 2011-12 recipient of the Trail Blazers' "Unify People in a Championship Culture" award. Prior to joining the team, Cronin earned his master's at the University of Denver, where he also worked as a graduate assistant for the men's basketball team. A Denver native who played college basketball at Regis University and the University of Northern Colorado, Cronin competed against Blazers head coach Chauncey Billups in the Colorado state high school basketball tournament.