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Roy has more than forty years of experience in banking, finance, and economic development. After graduation from college, he began his career in commercial lending with two Worcester-area financial institutions. He also worked with the Federal Deposit Insurance Corporation and the Commonwealth of Massachusetts Office of Business Development prior to joining MassDevelopment in 1998. Roy also has a long teaching career, having served as an adjunct professor of finance and economics at Assumption University for close to 25 years after stints at several other Worcester area institutions including Anna Maria College and Clark University. He has also served in a volunteer capacity with several different community organizations in the Worcester area, including Treasurer and President of the BOD for YOU, Inc. prior to its merger with Seven Hills Foundation in 2020. He also volunteered as a Big Brother and was a member of the BOD and Treasurer for Big Brothers Big Sisters of Central MA/Metrowest.