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Tom DiCostanzo began their work experience in 1988 at Allendale Insurance as a Web Developer. Tom worked in this role for eleven years until 1999. In the same year, they joined FM Global as a Principal Application Developer/Analyst, a position that they still hold.

Tom DiCostanzo attended the Community College of Rhode Island from 1997 to 2008, where they obtained an Associate's degree in Computer Science.