Upon graduating from law school, he accepted a position at Heenan Blaikie Law firm, where he practiced sports and entertainment law. In June 2006, he was hired by the Toronto Maple Leafs as their director of hockey administration. On August 24, 2007, Jackson was promoted to assistant general manager and director of hockey operations, working alongside then general managerJohn Ferguson Jr. When Ferguson was fired on January 22, 2008, Jackson remained as the team's assistant general manager under Cliff Fletcher. On September 12, 2008, Jackson was appointed the new general manager and governor of the Toronto Marlies, the American Hockey League farm club of the Maple Leafs. He also maintained his role as assistant GM and director of hockey operations. In March 2010, months after Brian Burke became the team's GM and president, Jackson left his position with the Leafs.
On August 3, 2023, Jackson was hired by the Edmonton Oilers to serve as CEO of hockey operations.[1] After the Oilers announced on June 27, 2024, that then-general manager Ken Holland's contract would not be renewed, Jackson assumed the role of interim general manager.[2] Jackson stepped down as interim general manager on July 24, with the Oilers' hiring of Stan Bowman.[3]
Jackson has appeared as a guest speaker and lecturer at numerous universities and conferences, including Harvard Law School and Osgoode Hall Law School.[4]