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Holly Claytor began their work experience in 2004 as a Media & Communications Specialist at Randolph-Macon College. Holly then joined Special Olympics Virginia, Inc. in 2007 as an Assistant Vice President, focusing on Media, Marketing, and Brand. Later, Holly took on the role of Vice President, Development & Communications at the same organization.

Holly Claytor attended the University of Virginia from 1998 to 1999, where they did not pursue a specific degree or field of study. Following this, they enrolled at Virginia Commonwealth University from 1999 to 2002, where they earned a Bachelor of Science (BS) degree in Mass Communications with a focus on print journalism.