At their February meeting, the Caroline County Board of Education unanimously reappointed Superintendent Dr. Derek L. Simmons to a new four-year term.
Following the vote, President Michele Wayman congratulated Dr. Simmons on the reappointment and mutually agreed-upon contract, and expressed appreciation for the leadership, dedication, and progress made in moving CCPS forward. “On behalf of the board, the students, the staff, the community, we welcome you back as superintendent.”
In his remarks, Dr. Simmons stated, “I’m absolutely honored, humbled and blessed to be able to continue the work in our county. To this board and our previous board … thank you for taking a chance on a career CCPS educator to rebuild and strengthen our (Caroline) family.” He expressed gratitude for the opportunity to lead the school system through post-pandemic challenges and the implementation of the Blueprint, and thanked the board for its confidence and support in renewing the superintendent’s term.
Dr. Simmons also expressed heartfelt gratitude to his family, in attendance, acknowledging the unique challenges of being married to a superintendent, especially when teaching in the same district. He praised his wife, Britt, as his best friend and the “glue” that keeps their busy life and chaotic schedule together, recognizing over 20 years of shared commitment to work and community. He also thanked their daughters for handling, with grace and poise, having a father who is also the superintendent. Dr. Simmons emphasized that none of his professional success would be possible without his family’s love and support.
“Thank you all and to our community, thank you to everyone who has been supportive,” Dr. Simmons said. “Serving our community has been a blessing … and I’m grateful for another four years to continue serving the community.”
Former board presidents James Newcomb and Rick Barton were in attendance and reflected on the significance and challenges of both sides desiring a second term in the office. Mr. Newcomb recalled being on the board 20 years ago when the last reappointment was made with Superintendent Dr. Edward W. Shirley. Mr. Barton added that the superintendent’s role is demanding, with the board witnessing firsthand the pressures, underscoring the dedication required for the position.
At the time of his first 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.
Through Dr. Simmons' leadership in his first term, the district strengthened and advanced the following:
• Climate & Culture: Strengthened the district’s sense of community through open communication, mutual respect, and collaboration across schools and departments.
• Employee Engagement & Retention: Strengthened compensation, benefits, and workplace supports, leading to higher retention and stronger recruitment.
• Blueprint Implementation: Expanded PreK/PreK3 access, increased National Board Certified teachers, improved student performance in literacy, math, and Advanced Placement, and broadened dual enrollment, apprenticeships, and Community Schools partnerships through collaborative efforts.
• Student Health & Wellness: With district school-based teams, expanded access to health and behavioral health services.
• District Efficiency: Improved operational efficiency and redirected resources to priority needs through energy initiatives, instructional reviews, and program evaluations.