Dr. Derek Simmons Named Superintendent Of Caroline County Schools


The Caroline County Board of Education has chosen a new superintendent.
Dr. Derek Simmons will take the position effective July 1st. Simmons has been serving as interim superintendent since March 2021.
Board president Jim Newcomb said a stakeholder survey last fall provided overwhelming feedback showing a desire for an appointment that would represent institutional knowledge, consistency and stability for Caroline County schools.
Simmons has been employed by Caroline County Public Schools for more than 20 years. He has received degrees from Salisbury University and Wilmington University.

“This is the most important job any Board of Education is charged with, and we wanted a fair and comprehensive search,” Newcomb said. “In following the process outlined by our search consultant, we were proud to find that it led to the best candidate for the job right here in Caroline, Dr. Derek L. Simmons.” 

Caroline County Public Schools provided this biographical information about Dr. Derek Simmons:

Dr. Simmons has been employed 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. 

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.