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Ritta Cunningham has a long work experience in various roles. Ritta began their career in 1995 as a Professional Staff Recruiter for Metro Information Services. In 1998, they moved to The Whitlock Group ebs as an IT Recruiter. In 1999, they became the Marketing Manager for Spectrum Therapy. In 2001, they took the role of Community Resources Manager at Edmarc Hospice for Children. In 2004, they became the Sales and Marketing Manager for EXCELerate Management Company, LLC. In 2010, they became the Business Development Manager for Pinpoint IT Services. In 2017, they became the Director of Operations for CollegeWeekends.com (CW LLC). In 2013, they founded their own company, RPC Management, where they are currently a Consultant/Owner.

Ritta Cunningham began their educational journey in 1987 at Monacan HS. Ritta then attended the University of Virginia from 1991 to 1995, where they earned a Bachelor of Arts in Psychology and German. In 2002, they began attending Virginia Commonwealth University School of Medicine and graduated in 2004 with a Doctor of Medicine.