Career
Prior to his entry into politics, Jackson was a human resources consultant. In 2004, Jackson ran for the Conservative nomination as the candidate in 2006 federal election in the riding of Barrie. He lost to Patrick Brown.
Brown went on to beat Liberal Aileen Carroll.
After Jackson lost the nomination, he was appointed to replace Brown as the city councillor for Barrie. He was re-elected as councillor in 2006 and continued in the position until 2011.
He ran in 2011 provincial election to replace Aileen Carroll. Jackson defeated Liberal candidate Karl Walsh by 2,521 votes.
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. 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.".