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Cheryl Reid Easterwood has an extensive work history in brand development, marketing, and sales. Cheryl began their career at Accenture (formerly Andersen Consulting), where they worked as a Senior Consultant from 1992 to 1996. Cheryl then moved on to Deloitte Consulting, where they held the position of Senior Consultant from 1997 to 1998. From 1998 to 2001, Cheryl served as the Director of Advertising Sales and later as the National Sales Manager for Travel Sales at USA TODAY. In 2002, they briefly took on the role of Director of Special Projects at USA TODAY. Cheryl then joined The Arizona Republic in 2003, where they worked as the Sr. Manager of Business Development and later as the Director of Republic Magazines & Custom Products from 2003 to 2006. Cheryl then returned to USA TODAY as the Regional Marketing/Sales Director for Circulation from 2007 to 2011. Cheryl spent the years 2012 to 2016 at GE Capital as the Strategic Relationships and Intelligence, Brand Management & Marketing. Currently, they hold the position of VP, Brand Development Officer - Franchise Finance at First Tennessee Bank, a role they have held since September 2016.

Cheryl Reid Easterwood pursued their undergraduate education from 1988 to 1990 at the University of Michigan-Dearborn, although the specific degree and field of study are not provided in the information. Following this, they attended Wake Forest University from 1990 to 1992, where they obtained a Bachelor of Science (BS) degree in Business. Later, in 1996 to 1997, Cheryl pursued higher education at the University of Notre Dame - Mendoza College of Business and obtained a Master of Business Administration (MBA) degree. The field of study for their MBA is not mentioned.