Jackson played professionally as a quarterback in the CFL for eight seasons with the Lions and one year with the Argonauts where he won three Grey Cup championships in 2006, 2011, and 2012.

[1] Jackson attended the University of Notre Dame, where he was a two-year starter and set school single-season records for passing yards (2,753), completions (184), and attempts (316) as a senior during the 1999 season.

[2] Pro scouts projected that Jackson could develop into a solid NFL quarterback if placed into the right system.

[1] Jackson also spent one season (2001) in Barcelona, as part of NFL Europe, where he competed in the 2001 World Bowl.

He began 2005 on the practice squad as the fourth-string quarterback, but was elevated to the active roster when CFL superstars Dave Dickenson and Casey Printers went down with injuries, followed by third-stringer Buck Pierce.

On February 6, 2020, it was announced that Jackson was joining the Toronto Argonauts as the team's offensive coordinator and quarterbacks coach.

[12] The 2020 CFL season was cancelled, but Jackson coached for the Argonauts in 2021 where the team finished in first place in the East Division.

On January 4, 2022, Jackson formally joined the Edmonton Elks as the team's pass game coordinator and quarterbacks coach.

[15] He posted a 7–6 record in the remaining 13 regular season games, but the Elks failed to qualify for the playoffs for the fourth consecutive year.