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Chessie Ralston has extensive work experience in the marketing field. Chessie started their career in 2002 as a Customer Service Representative at John Hancock Investments and then transitioned to the role of Marketing Communications Specialist in 2003. In 2006, Chessie joined Capitol Financial Solutions as a Marketing Coordinator and quickly progressed to become the Director of Marketing in the same year. Chessie held this position until 2011 when they were promoted to Vice President of Marketing. Most recently, Chessie served as the Chief Marketing Officer at Capitol Financial Solutions starting in March 2020.

Chessie Ralston completed their secondary education at East Hampton High School from 1993 to 1997. Chessie then pursued a Bachelor of Science degree in Marketing at Lynchburg College from 1997 to 2001.