Jackson grew up in Pointe-Claire, QC where he began skating at a young age. His older brother played hockey and his father was an NHL referee at the time. Jackson played hockey throughout his high school days and eventually earned a scholarship to play at Pomfret School, a prep school in CT. After Pomfret, he played two years of junior hockey in Portland, ME and Hawkesbury, Ontario. In 2016, Jackson attended the NHL Exposure Combine where he got his feet wet and was exposed to the world of officiating outside of what he experienced through his dad’s career. Jackson became a freshman at Manhattanville College soon after, where he played NCAA hockey for 4 years and captained his team during his Junior and Senior seasons. In 2020, Jackson graduated from Manhattanville while the Covid pandemic first reached the United States. Once his senior season ended, he landed a spot playing for the Fayetteville Marksmen in the SPHL for the remainder of their 2019-2020 season. The winter of 2020 rolled around and Jackson signed a contract with the Maine Mariners in the ECHL for the 2020-2021 season, however the team opted out of that season last minute due to the ongoing pandemic. Jackson found a spot on the Birmingham Bulls later that season as the SPHL was still operating with 5 teams. After the 2021 season, Jackson realized that his playing days were numbered, and made a commitment to officiating. He attended the 2021 NHL Exposure Combine once again, where he landed a job as a linesman in the AHL for the following season. After the 2021-2022 AHL season came to a close, Jackson was hired to a minor leagues contract by the NHL during that offseason..