Montgomery started skeleton racing when he lived in Calgary where he worked as an auctioneer not far from Canada Olympic Park in Calgary. Sometime in 2002 he visited the track with his parents where a skeleton race was being held. He was immediately hooked on the sport and soon started racing competitively. Initially he did not do well in his first two seasons competing on the World Cup tour. However, he won his first World Cup race in Cesana, Italy, in 2008. He won two silver medals at the 2008 FIBT World Championships in Altenberg, Germany, in the men's skeleton and mixed bobsleigh bobsleigh-skeleton team event. His highest World Cup overall placing came when he finished second overall in the 2007–08 Skeleton World Cup.