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Kevin J. Flanagan has a diverse work experience in finance and management roles. Starting in 2003, they worked as an Accountant at ARAMARK before moving up to the position of Financial Analyst, where they prepared financial projections and analyses for senior management. In 2010, they were promoted to Senior Financial Analyst, where they rolled up financial performance reports and maintained budgets for multiple business units. In 2012, they joined Five Below as a Senior Financial Analyst, overseeing financial planning and budgeting. Since 2013, Flanagan has been working at the BIG EAST Conference, first as a Business Officer, managing day-to-day finances and serving as a liaison to the Board of Directors. Kevin J. was later promoted to Associate Director, Budget & Finance, where they developed budget strategies, managed financial reporting, and directed the conference's men's basketball tournament, the main revenue generator.

Kevin J. Flanagan holds a Master of Business Administration (MBA) degree in International Business from Villanova University. Kevin J. also obtained a Bachelor of Science (BS) degree in Finance from the same institution. In addition to their formal education, they participated in an International Study Practicum at East China Normal University and an EU Parliament Practicum at the College of Europe. Prior to their higher education, Kevin attended St. Joseph's Prep. However, specific details such as the start and end years for each educational experience are not provided.