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Drew Sivers has a diverse work experience in various roles within the sports industry. Drew began their career as a Training Manager at Sporting Life in 2000. Drew then worked at Salomon Canada as a Territory Manager and later as a Regional Sales Manager, where they managed all sales and marketing aspects for different categories within the brand. In 2007, they became a Principle at PUSH Sales Agencies. From 2013 to 2017, Drew served as the Country Commercial Manager for Salomon WSE in Canada, responsible for managing commercial fundamentals for winter sports. Drew then moved on to become a Portfolio Sales Manager at Amer Sports Corporation, staying with the company until 2019. Currently, Drew serves as the Market Director at Salomon, a position they have held since 2020.

From 1990 to 1992, Drew Sivers attended Queen's University. However, specific details about the degree pursued or field of study are not mentioned.