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Garrett Matthews' work experience began in 2008 as an Assistant Coordinator at Championship Lacrosse Camp. Garrett then interned at T. Rowe Price from May 2011 to August 2012. In 2012, they worked as an OIP Site Acquisitions and Advertising Agent at Outdoor Income Partners LLC. Starting from 2013, Garrett had roles at Compass Group as a Regional Sales Director, then at Canteen Vending as a Regional Sales Director providing office coffee and refreshment services. Garrett also worked as a Sales Executive at Vocus, a leading provider of cloud-based marketing and PR software. In 2014, Garrett joined Tenable as an Inside Sales Representative - Enterprise and later became a Territory Sales Manager. Currently, they are employed at ID.me as an Enterprise Account Executive, starting from January 2021.

Garrett Matthews attended Washington College from 2008 to 2012, earning a Bachelor of Science (BS) degree in Business Administration and Management, General. No further information is available about their education history after completing their bachelor's degree.