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Gwen Calhoun has a diverse work experience spanning over several decades. Gwen began their career as a Store Manager at Red and White Supermarket in 1982, where they gained experience managing all departments of the grocery store. In 1992, Gwen joined Southern Bank as a Loan Processor. After three years, they moved on to First South Bank in 1995, taking on the role of Vice President in Special Assets, focusing on collections, bankruptcy, and foreclosures. First South Bank later merged with CresCom Bank in 2017, and Gwen continued their role as Vice President, overseeing Collections, Foreclosures, and Bankruptcies. Throughout their career, Gwen has demonstrated a strong understanding of banking operations and has played a key role in managing and resolving financial challenges for their employers.

Gwen Calhoun attended Creswell High School until 1978. Gwen then pursued some business courses at both the College of the Albemarle and Martin Community College.