Rubuta ci gaba don wannan sakin layi - Montgomery ya fara tseren kwarangwal lokacin da yake zaune a Calgary inda ya yi aiki a matsayin mai sayar da kayayyaki ba da nisa daga Kanada Olympic Park a Calgary. A wani lokaci a shekara ta 2002 ya ziyarci filin tsere tare da iyayensa inda ake yin tseren ƙwallon ƙafa. Nan da nan ya soma sha'awar wannan wasan kuma ba da daɗewa ba ya soma yin tsere. Da farko bai yi kyau ba a farkon lokacinsa biyu na gasar cin kofin duniya. Duk da haka, ya lashe gasar cin kofin duniya ta farko a Cesana, Italiya, a shekara ta 2008. Ya lashe lambobin azurfa guda biyu a gasar zakarun duniya ta FIBT ta 2008
a Altenberg, Jamus, a cikin tsarin maza da bobsleigh da bobsleigh-skeleton na hadadden rukuni. Matsayin da ya fi dacewa a gasar cin kofin duniya ya zo ne lokacin da ya gama na biyu a gasar cin kofin duniya na Skeleton na 2007-08.