Dr. Derek L. Simmons, Superintendent of Schools
superintendent@ccpsstaff.org
Appointed July 1, 2022
At this time of his appointment in 2022, Dr. Simmons had been with with CCPS for over 20 years, beginning his career in 2001 as a social studies teacher at Colonel Richardson High School (CRHS). In 2005, he was appointed assistant principal at CRHS, followed by the principalship in 2008. Dr. Simmons became a supervisor of instruction in 2012 and director of student services in 2014. Prior to his appointment in 2022, he served as interim superintendent.
In various capacities, Dr. Simmons has represented CCPS with multiple groups including Caroline County Planning Commission, the Local Drug and Alcohol Abuse Council, the Eastern Shore Mental Health Coalition, YMCA of the Chesapeake Advisory Board, Caroline County Recreation & Parks Advisory Board, the Denton Rotary, Food for Learning and the Caroline Wellness Coalition. He is a member of the Maryland Athletic Directors Association, the National Interscholastic Athletic Administrators Association, the School Superintendents Association (AASA), the Public School Superintendents Association of Maryland, and the Eastern Shore of Maryland Educational Consortium. Dr. Simmons is a graduate of Shore Leadership and Leadership Maryland, and has served on committees for both organizations.
Dr. Simmons received his Bachelor’s and Master’s degrees from Salisbury University, and earned his Doctorate of Education in Innovation and Leadership from Wilmington University. He was awarded the Aubrey K. Doberstein Leadership Award which is presented to a graduating doctoral student for outstanding leadership and dedication to the philosophy and mission of Wilmington University.
