Simmons photo

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.

Superintendent's 2025-2026 Goals

Goal 1: Improve academic achievement outcomes for all students, disaggregated by student groups.

  • Increase percentage of students on grade level in reading.

  • Increase percentage of student on grade level in mathematics.

Goal 2: Enhance efforts for one and two way communication between Caroline County Public Schools and the community.

  • Increase community with parents, elected officials, community organizations, and local businesses with emphasis on diverse populations.

Goal 3: Strengthen Caroline County Public Schools professional culture among staff.

  • Strengthen recruitment and retention efforts, and develop practices that build a professional staff that reflects the diversity of our student body.

  • Improve internal communications between school sites and districtwide offices, and break down perceived barriers between schools/levels/divisions.

Goal 4: Ensure successful implementation of the Blueprint for Maryland's Future and the Strategic Plan.

  • Approval and implementation of CCPS Blueprint plan, and timely submission of all required reports.

Goal 5: Ensure efficient and effective use of the CCPS budget and grants to support the mission and vision.

  • Financial records and audit reports demonstrate efficient use of funds.

  • Proposed budget submitted to the board reflects priorities of the school system.

Organizational Chart

Contact:

Rachel Barry, Executive Assistant to the Superintendent and Board of Education
410-479-3250 x1160 
barry.rachel@ccpsstaff.org