Osmond began skating at age three, following her elder sister Natasha. Due to a lack of ice during the summer in Marystown, they often travelled to Montreal to train. Since the age of ten, after her parents came west because of work in the oil industry Osmond trained at the Ice Palace Figure Skating Club in Edmonton, coached by Ravi Walia with choreography by Lance Vipond.
In the 2011–12 season, Osmond competed on the senior level for the first time at the Canadian Championships. She was first after the short program, ahead of the defending champion Cynthia Phaneuf and the 2011 bronze medallist Amelie Lacoste. Osmond won the bronze medal overall. At the 2012 World Junior Championships, Osmond won the preliminary round. She finished tenth overall.
Osmond's national championship resulted in her being named as the lone Canadian ladies' singles skater at the 2013 World Championships in London, Ontario. She placed a surprising fourth in the short program, which many in the Canadian skating community considered "the best global championship debut by a Canadian woman since the 1970s." Osmond struggled in the middle section of her long program, falling twice and stepping out of another jump, and placed tenth in the long program, for an eighth-place finish overall. This result secured two spots for Canada at the 2014 Winter Olympics. Interviewed afterwards, Osmond stated: "I had a little thought of a possible medal in my head, but I put it out of my mind and focused on my goal, which was top 10."
Osmond trained in southern California for about two weeks in August 2013 under the guidance of Walia and Frank Carroll. Due to a stress reaction in her left ankle, she was off the ice for most of September 2013. In late October, she competed at the 2013 Skate Canada International, placing fifth in the short program, but pulled out before the free skate due to a torn hamstring in her right leg. She also withdrew from the 2013 Rostelecom Cup but returned to competition at the 2014 Skate Canada Challenge. At the 2014 Canadian Championships, she placed first in both segments and repeated as national champion.
This was the first time Osmond participated in all the major competitions of the season: the Grand Prix series up to the final, the Canadian National, the Four Continent Championships, and the World Championships. She did not participate in the World Team Trophy at the end of the season.
Osmond's short program for the 2016–17 season, a medley of songs by the French singer Edith Piaf, would become her most acclaimed program to date, with Excelle Sports describing it as "widely heralded as tops among all 2017 offerings." Time would later praise it as "exuding a flirty sensuality reminiscent of Cyd Charisse." For her long program, Osmond had initially hoped to skate a version of Black Swan and Swan Lake. Both her coach, Ravi Walia, and her choreographer, Jeffrey Buttle, suggested La boheme as an alternative to further develop her performance ability, and this was ultimately adopted.
On June 4, 2018 Osmond announced that she was planning to skip competitions on the Grand Prix series. The following day her participation in the cross-Canada "Thank You Canada Tour" was announced. On August 21, 2018 Osmond confirmed that she would not compete at all during the 2018–2019 season. She subsequently stated that her return to competitive skating is uncertain. On May 2, 2019, Skate Canada announced her retirement from competitive skating.
Osmond spins and jumps clockwise. She has landed 3F-3T, 3T-3T, 3S+2T+2Lo, 2A+2T+2Lo, and 2A-3T combinations in competition.
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