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James Kessler has a diverse work experience spanning over several high-level positions in various companies. James started their career at Pep Boys, where they held multiple Vice President roles in operations, administration, financial planning, analysis, and merchandise supply chain and services. James then worked at City Sports as the Chief Financial Officer & Chief Operating Officer before joining vRide as the Chief Operating Officer & Chief Financial Officer. Kessler later became the Chief Operations Officer at ABRA Auto Body & Glass and served as the President, Emerging Business at Caliber Collision. After that, they took up the role of President & Chief Operating Officer at Ritchie Bros. Currently, Kessler is the Chief Executive Officer at RB Global Inc.

James Kessler earned their Bachelor of Science degree in Finance from Saint Joseph's University from 1990 to 1994. James later pursued a Master of Business Administration (MBA) in Finance from the same university from 1996 to 2000.