After a successful season at FIS level , Fleckenstein entered the Nor-Am Cup in the 2014/15 season , where she initially competed in all disciplines except downhill. Her second season was very successful with several top results, including a third place. In March / April 2016 she won seven out of eight FIS races in succession in her hometown of Whistler . At the beginning of the third Nor-Am season, she celebrated a victory at her first downhill start in Lake Louise and ended the winter of 2016/17 in fourth overall and second in the downhill classification. At the Junior World Championships in Åre, she classified in all disciplines, but fell short of her expectations in downhill and super-G. In the team competition she won the first Canadian gold medal in this discipline with her teammates.
On December 2, 2016, Fleckenstein made her World Cup debut in the Downhill from Lake Louise . After two more starts, she was crowned Canadian downhill champion for the first time just a few days later at the same location .