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Justin A. Diamond has a diverse work experience ranging from media planning at Hill Holliday starting in 2013 to working as a cashier, hostess, expediter, drive-thru operator, and assistant manager at Kelly's Roast Beef from 2010 to 2011. In between, they worked at eBay Inc in a business role at Jadmyparts and at Abercrombie & Fitch as a sales associate/manager, where they conducted research, wrote reports, and prepared financial documents for the CFO.

Justin A. Diamond completed an Associate's degree in Business Administration and Management, General at North Shore Community College from 2011 to 2013. In 2013, they also attended North Bennet Street School, where they focused on jewelry fabrication. From 2013 to 2015, Justin attended Babson F.W. Olin Graduate School of Business to pursue studies in Business Administration and Management, General, though no degree is specified.