Jackson has been playing soccer since he could barely walk, being coached and trained by his father, Jason Watson. He was coached to be a strong, on the ball attacker, with a lightning first touch and a feel for creating scoring opportunities.

Jackson has led his club team for 3 straight years in goals and assists. He made the varsity team at Haddonfield Academy as a freshman and was a starter, coming in second for goals and assists for the season.

The club team Jackson plays on is a USYS team ranked #3 in New Jersey and #38 in the USA. He as well plays on the New Jersey 2010 Olympic Development Progam, a private school 2009 team, and a national futsal competition team.