In January 2014 Jackson led team-mates Joel Fearon, Stuart Benson and Bruce Tasker to a silver medal in the four-man event at the Bobsleigh European Championship. He competed at the 2010 and 2014 Winter Olympics, guiding his crew to fifth place in the four-man event in 2014, 0.11 seconds off a bronze medal after recovering from a ruptured Achilles tendon. In 2017, the British team were upgraded to the bronze medal position after two Russian crews were disqualified for doping violations. Jackson also competed at seven FIBT World Championships, finishing fifth in the four-man event in the 2013 Worlds at St. Moritz. He took a second place in the four-man competition at the Lake Placid round of the 2013–14 Bobsleigh World Cup, the first podium finish for a British crew for many years. Jackson announced his retirement from the sport in June 2016.