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Jessica Crough started their work experience in 2007 as a Data Management Analyst at MassMutual, where they were responsible for recordkeeping complex retirement plans and ensuring the accuracy of tax forms. In 2010, they became a Retirement Services Accountant, where they performed accounting research, analyzed financial statements, and collaborated with operational and financial business partners. In 2013, they were promoted to Senior Accounting Director, leading a team of 18 Accounting Consultants and overseeing the daily operations of the Finance department. Jessica also served as the Divisional Tax Leader for Retirement Services, ensuring accurate and timely completion of tax reporting. In 2018, they joined MGM Springfield as the Director of Finance.

Jessica Crough obtained their Associate's degree in Accounting from Holyoke Community College, where they attended from 2004 to 2006. Jessica later pursued a Bachelor's degree in Business Administration and Management, with a focus on General Management, at Western New England University from 2008 to 2011.