In 2004, Jackson ran for the Conservative nomination as the candidate in 2004 federal election and 2006 federal election in the riding of Barrie. He lost to Patrick Brown.[5][6] Brown went on to beat Liberal Aileen Carroll in 2006.[7]
After Jackson lost the nomination, he was elected in 2006 to replace Brown as the city councillor for Barrie. He was and continued in the position until 2011.[8] He ran in 2011 provincial election to replace Aileen Carroll. Carroll, after losing federally went on to win the provincial riding of Barrie, served for one term and then decided to retire. Jackson defeated Liberal candidate Karl Walsh by 2,521 votes.[4][9] He served as party critic for the 2015 Pan American Games and critic for community and social services.
In September 2013, Jackson was accused of terminating a part-time employee citing insufficient funds and then advertising the same position as an unpaid internship. Jackson said the accusation was, "patently untrue." The Ministry of Labour was called in to investigate the situation.[10] After an initial investigation by the Ministry of Labour the allegations against Jackson were proven to lack substance and the complaint was not pursued by the Ministry.
In the June 2014 provincial election, Jackson was defeated by Liberal candidate Ann Hoggarth. Jackson attributed his loss to provincial unions. He said, "I think the unions misrepresented what we were talking about and we paid the price."[11]
Jackson ran for the Conservative nomination as the candidate in the 2015 federal election. In July 2015, he was lost the nomination to City Councilor John Brassard who went on to win the riding.[12]
Jackson introduced two Bills during his tenure, the "Blocker Ban Bill", Bill 88, which looked to ban the proactive use of foam blockers by workers responsible for caring for autistic children and young adults.[13][14] The second Bill titled "Youth Right to Care", Bill 102, was introduced to protect 16 and 17 year old children entering care for the first time and closed an age old gap that prevented these children from accessing welfare services from the province. The Bill received all party unanimous support.[15][16]