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Alicia Gillespie started their work experience in 2002 as a Bursar at Volunteer State Community College, where they worked until 2005. In 2005, they joined the Tennessee Board of Regents as an Assistant Director of Financial Accounting.

Alicia Gillespie pursued their education in a chronological manner. Alicia first attended Volunteer State Community College from 1998 to 2000, where they obtained an Associate of Science degree in Business/Commerce, General. Following this, they enrolled at Middle Tennessee State University (MTSU) from 2000 to 2002 and completed their Bachelor of Business Administration (BBA) degree with a focus in Accounting. Lastly, in the years 2003 to 2005, Alicia attended Tennessee Technological University, where they earned their Master of Business Administration (MBA) degree with a concentration in International Business.