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Tom Caswell has an extensive work experience in the field of Information Technology. Tom started their career at FiberPlus Inc in 1994 and held various roles during their tenure. Tom began as a Team Leader/ Project Manager and eventually worked their way up to become the Vice President. As Vice President, they held responsibility for FiberPlus Federal Services Group and FiberPlus Inc. After leaving FiberPlus Inc, Tom joined SCD Information Technology in 2022 as the Deputy Director of the Infrastructure Division.

Tom Caswell attended the University of Baltimore from 1985 to 1988, where they earned a BA in Science from the School of Business. Tom also attended Anne Arundel Community College but the start and end years are not provided. At the community college, they pursued an Associate of Arts (AA) in Environmental Science. Additionally, Tom Caswell attended Chesapeake High School, although no specific degree or field of study is mentioned.