Dean started his Playing Career, as a Centre Half, at Walsall in 1989, making 142 appearances. He then signed for Hereford United, appearing 117 times for the Club. He then went on to play for Leyton Orient, making 239 appearances. He then moved to Sheffield Wednesday and finished his career at Port Vale. He then moved into Management, where he moved back to Orient as an Assistant Manager. He was then appointed Head of Youth at Walsall, and then promoted to Manager in 2011. He took Walsall to the 2015 Final of the Football League Trophy. He is now the current Manager of Championship Club Brentford.