Jent was an assistant coach for the Philadelphia 76ers in the 2003–04 season. The next season, he worked in the same capacity with the Orlando Magic, and was appointed interim head coach for the final 18 games of the 2004–2005 season (going 5–13), after Johnny Davis was fired. At the start of the next season he was replaced by Brian Hill. Beginning in November 2006, Jent took on the role of Assistant Coach/Director of Player Development with the Cleveland Cavaliers. He served as LeBron James' personal shooting coach while James was on the team.