Dean came through the Oakleigh Chargers program in the NAB league, captaining the club to a premiership in 2006 and playing for Vic Metro in the State championship games.  He then continued his football at Port Melbourne in the VFL and Vermont in the Eastern Football League. 

He worked as a Victorian Police officer for 13 years whilst being an assistant coach within the Oakleigh Chargers and Caufield Grammar School football programs. After moving to Sydney to support his partner, who is playing for the Swans AFLW team, he continued his career in multiple roles at the club including facilities manager, AFLW development coach, match day runner and VFL assistant coach.

After serving as an Academy coach for the U16 Male program he stepped up into a VFL coaching position at the end of 2023.