Born in North Vancouver, British Columbia, Osborne-Paradis grew up racing for the Whistler Mountain Ski Club.

His first World Cup podium came in November 2006 at the Bombardier Winterstart men's downhill in Lake Louise, Alberta, Canada.

In April 2008, he joined forces with teammate Mike Janyk to provide a four-day training camp free of charge to underprivileged Canadian racers from around British Columbia.

On 29 January 2011, Osborne-Paradis crashed badly at the downhill race in Chamonix, France, and was airlifted by helicopter and treated for a broken fibula.

Osborne-Paradis was a surprise bronze medalist in super-G at the 2017 World Championships, behind teammate Erik Guay and Norway's Kjetil Jansrud.