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Sam Dewey has a diverse work experience spanning over several years. Sam started their career in 2006 as a Valuation Analyst at Wisehart & Wisehart, and later worked as the Director of Finance at CW Financial from 2007 to 2010. In 2012, they joined Clayton Dubilier & Rice as a Summer Associate. Later that year, they moved to Relias, where they held various roles including Director of Strategic Programs, Director of Finance, VP of Client Care, and Chief Corporate Development Officer. In 2020, Sam became a Consultant & Investor at GSD LLC, and also worked as a Global Client Care Assessment and Remediation Consultant at insightsoftware from 2020 to 2021. Currently, Sam serves as the Senior Vice President of Growth at Tripleseat, a position they have held since 2022.

Sam Dewey attended the College of Charleston from 2002 to 2006, where they obtained a Bachelor of Science degree in Economics. Later, from 2011 to 2012, they attended the Columbia Business School and earned an MBA degree. The field of study for their bachelor's degree was Economics and Finance, while no specified field of study was provided for their MBA.