Originally from Carey Grammar, Jackson was drafted to Richmond from the Oakleigh Chargers in the TAC Cup with the 53rd selection in the 2003 AFL Draft. He went on to play 156 games for the Tigers, predominantly as a midfielder and lockdown player, and was a member of the club's leadership group from 2009 to 2014.
In 2013, Jackson won the Jack Dyer Medal, making him the oldest player to win the club's Best and Fairest for the first time since Matthew Richardson in 2007. He also won the club's Jack Titus Medal for runner-up Best and Fairest in 2009.
On 5 September 2014, Jackson announced his immediate retirement from AFL football, citing the toll injuries had taken on his body.[1]
Continuing with his passion of helping people and community work, Jackson has created Foundation Performance to maximise individual performance capabilities.[2] He also travelled and volunteered in Nepal with THISWORLDEXISTS, an Australian nonprofit to hike to Everest Base Camp and support educational improvements in Nepalese communities.[3]