As starting QB, Gleeson led the Glen Ridge football squad to a winless season.
In 2006, while splitting time as a senior, Gleeson helped lead his team to an 8–0 record, and combined with his co-quarterback partner to throw for over 4,000 yards, all while on the path to claiming the NESCAC title.
[3] Following Gleeson's playing days and graduation from Williams College, he spent 2007 through 2010 at Delbarton School in Morristown, New Jersey.
[2] In 2011, Gleeson joined Brian Surace's staff at Fairleigh Dickinson-Florham as the offensive coordinator and quarterbacks coach.
Kanoff broke the Princeton and Ivy League records for single-season passing yards with 3,474, and he also broke the Ivy League single-season completion percentage of 73.2, breaking the mark held by former Dallas Cowboys head coach and former Princeton Bushnell Cup winner Jason Garrett.
[5] The signed contract made Gleeson the highest paid assistant coach in Rutgers University history.