Dr. Derek L. Simmons Appointed Caroline Superintendent of Schools


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The Caroline County Board of Education announced the selection of Dr. Derek L. Simmons as superintendent, effective July 1, 2022. The appointment to a four year contract was approved at the May board of education meeting.

“This is the most important job any Board of Education is charged with, and we wanted a fair and comprehensive search,” Board President Jim 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.” 

Dr. Simmons was appointed interim superintendent by the Board in March of 2021, which provided time for the Board to conduct a thorough search. In October, the Board contracted with the Maryland Association of Boards of Education (MABE) to lead the search which involved a stakeholder survey, application review, and several rounds of interviews, including one with a representative group of staff and community members. 

President Newcomb referenced the stakeholder survey conducted in November of 2021. “Feedback overwhelmingly showed a desire for an appointment that would represent institutional knowledge, consistency and stability. Luckily for us, Dr. Simmons’ skill set and experience made him the top choice and exactly what our community wanted, and a perfect fit for Caroline.”

Dr. Simmons was joined at the meeting by his spouse, Brittainy Simmons. Ms. Simmons is a Media Specialist at Federalsburg Elementary School in Caroline; daughters Siena and Chloe both attend Colonel Richardson Middle School. Caroline County Commissioners Wilbur Levengood and Dan Franklin were also in attendance, along with Delegate Jeff Ghrist

In accepting the appointment, Dr. Simmons shared his 20+ year journey with the school system and said the “Caroline bug” bit when he began as a student teacher at Lockerman Middle. After settling at Colonel High, he knew Caroline would always be home. He thanked his wife Brittainy, “an amazing partner and best friend,” and his daughters, the Board for their confidence and support and the Caroline commissioners who work hand in hand with the school system. He acknowledged the incredible community that wraps around each child to meet their needs. Lastly, Dr. Simmons thanked the CCPS staff and promised to work as hard as they do each and every day.  


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.


Contact:   Sandi Barry, Communications Officer  |  [email protected]  |  [email protected]