A native of Portsmouth, Virginia, Mrs. Caldwell began her career in education as a junior high school teacher in Fauquier County, Virginia, in 1975. Mrs. Caldwell moved to Virginia Beach where she began teaching English at Kellam High School in 1977. She taught at Green Run High School from 1979 to 1989, and then moved to Salem High School where she taught from 1989 to 1992.
Mrs. Caldwell became an administrative assistant at Brandon Middle School and Cox High School in 1992. Her first administrative post came in 1993 when she served as assistant principal at First Colonial High School. In 1997, Mrs. Caldwell became principal of the Bayside Sixth Grade Campus. She left in 1999 to become principal at Corporate Landing Middle School where she stayed until 2001. From 2001 to 2003, Mrs. Caldwell served as principal of Salem High School, and from 2003-2009 she served as principal of Tallwood High School. As a member of the Superintendent’s cabinet, she served as the Assistant Superintendent for High School Education in the Department of School Administration from July 2009 – 2013. She continues to serve on the Executive Leadership Team in her new position as Director of Equity Affairs.
As the Co-Chair of Strategic Objective Three, the division’s Strategic Plan – Compass to 2015, which states, “Each school will improve achievement for all students while closing achievement gaps for identified student groups, with particular focus on African American males.” The new role fits Mrs. Caldwell’s passion for all students to receive the benefits of the quality instruction and vast opportunities Virginia Beach City Public Schools offer to children. A thirty-five year veteran of this school division, she has been a champion for all students her entire career. She is happy to expand her role as a school leader as she represents the school division’s efforts to include all citizens’ groups to assure a quality education for young people.
Mrs. Caldwell received a Bachelor of Arts Degree in English from Virginia State University. She earned a Master of Science Degree in Administration from Old Dominion University. Mrs. Caldwell is a member of various professional organizations, was named Virginia Beach Secondary Principal of the Year for 2001-2002, and is a recipient of the regional Women of Distinction Award from the Hampton Roads YMCA. She was recently appointed to serve on the Tidewater Youth Services Commission.