Cynthia served as a Deputy Attorney General in the Office of Attorney General Mark Herring from 2014 until her retirement in 2019. Earlier in her career, Cynthia served under two other Attorneys General and as an agency head under Governors Baliles and Wilder. Cynthia also has spent time as environmental counsel for a paper and consumer products company.

Over the years, Cynthia has been engaged in many community organizations. She has served on Boards for the Virginia Foundation for Public Media, the Library of Virginia Foundation, Jewish Family Services, and on the Virginia Institute of Marine Science Council, to name a few. Many Boards in which she was a member, she served in a leadership role, including Chair of the City of Richmond Personnel Board, Chair of the Commonwealth Public Broadcasting Corporation Board, Chair of the Community Station Board for WCVE-FM, and currently she is serving as Vice-Chair on the Virginia Foundation for Public Media Board.

Cynthia earned her law degree from the University of Richmond and her undergraduate degree from The College of William and Mary.

"I had the privelege of working with Ms. Bailey while serving as University Counsel to Virginia Commonwealth University. VRA is fortunate to have Ms. Bailey's expertise on the Board and we look forward to furthering VRA's mission under the guidance of dedicated Board members such as Ms. Bailey."Stephanie Hamlett, Executive Director