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Glenn Chambless began their career in IT at Sun Life Financial in 1995 as a Customer Service/Group Operations Representative before transitioning to a Business Systems Analyst. Glenn held various IT roles at the company until 2013 when they joined Group 1001 as Director, IT.

Glenn Chambless completed their high school education at Framingham South High School from 1986 to 1989. Glenn then went on to attend North Adams State College in 1989 before transferring to Framingham State University, where they graduated in 1994 with a Bachelor of Science in Business Administration and a minor in Psychology.