Jason came through the underage system at Cobh Ramblers and was a part of the club's 2011 A Championship squad. He left later that year to go to the US where he joined the soccer programme at Boston College. In 2012 Jason joined up with Cork City's U19 squad where he was part of the side that won the league and Cup double.

In 2013/14 Jason turned out for UCC in the Munster Senior league and was part of the team that reached the second round of the 2014 FAI Cup. He returned to the League of Ireland in June 2015 when he rejoined Cobh Ramblers, making 14 league appearances before the season's end, netting three times in the process, as Cobh finished sixth in the First Division. In 2016 Jason made a further 12 league appearances as the Rams finished third and made it to the promotion play-offs where they lost out to Drogheda Utd in the semi-finals.

In December 2016 Jason signed up for a third season with the Ramblers but departed Cobh in July 2017 due to work and study commitments. In August he signed for MSL side Cobh Wanderers.