Simmons photo

Dr. Derek L. Simmons, Superintendent of Schools

superintendent@ccpsstaff.org

Appointed July 1, 2022

Reappointed to Second Term Feb., 2026

Dr. Derek L. Simmons was first appointed superintendent of Caroline County Public Schools in 2022 and was unanimously reappointed to a new four-year term in 2025. At the time of his initial appointment, he brought more than 20 years of service to Caroline, having begun his career in 2001 as a social studies teacher at Colonel Richardson High School. His career reflects a deep commitment to the district, with leadership roles including assistant principal and principal at CRHS, supervisor of instruction, director of student services, and interim superintendent.

During his first term, Dr. Simmons helped strengthen the district’s sense of community through open communication, collaboration, and mutual respect. Under his leadership, CCPS made progress in employee engagement and retention, advanced implementation of the Blueprint for Maryland’s Future, expanded early childhood programs, increased National Board Certified teachers, and strengthened academic outcomes. The district also broadened dual enrollment, apprenticeship, and Community Schools partnerships, expanded student health and behavioral health services, and improved operational efficiency through thoughtful planning and strategic initiatives.

Dr. Simmons is an active member of the School Superintendents Association (AASA), the Public School Superintendents Association of Maryland, and the Eastern Shore of Maryland Educational Consortium. He is a graduate of Shore Leadership and Leadership Maryland.

Dr. Simmons earned his bachelor’s and master’s degrees from Salisbury University and his Doctorate of Education in Innovation and Leadership from Wilmington University, where he was honored with the Aubrey K. Doberstein Leadership Award for outstanding leadership and service.

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