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Win Bear has a wealth of work experience, beginning in 2000 when they joined SVB Financial Group as an Associate. In 2002, they moved to RBC as a Senior Account Manager for Knowledge Based Industries. In 2007, they joined Silicon Valley Bank as a Managing Director. In 2019, they became the Head of Business Development for Canada at SVB Financial Group. In 2020, they joined Kensington Capital Partners Limited as a Managing Director of Venture Capital. In 2021, they became a Board Director at Borrowell and a Board Member at Drop. In 2022, they joined both Vetster Inc. and TheGuarantors as a Board Member.

Win Bear attended the University of North Carolina at Chapel Hill from 1994 to 1998, where they earned a BA in English. Win then went on to the UNC Kenan-Flagler Business School, where they earned an MBA in 2008.