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DENTON – The Caroline County Board of Education voted in February to renew Dr. Derek Simmons’ contract as Superintendent of Caroline County Public Schools. This is the first time in 20 years that CCPS has renewed a Superintendent, and Dr. Simmons says he doesn’t take the opportunity for granted. For his next four year installment, he plans to focus on strengthening academic outcomes, maintaining a positive staff (or what he calls the “Caroline Family”) culture, advancing major construction projects, and expanding career-based learning opportunities for students.
Simmons’ perspective on those priorities is shaped by a career that began in the classroom. He entered the district in 2000 as a social studies teacher at Colonel Richardson High School, starting midyear after student teaching locally. From there, he has served as a tennis and volleyball coach, assistant principal, principal, and eventually moved into central office leadership, where he technically dealt with social studies education. But “as the social studies guy, you catch everything,” he said, so he had responsibilities in athletics, gifted and talented, health and physical education, and more. Simmons actually pitched the idea of having a Director of Student Services, a position which he then took on before becoming an interim and now full-blown Superintendent. His breadth of experience, he said, came from a simple mindset: “If you see a need, fill a need.”
Serving as the Director of Student Services taught Simmons a great deal about good leadership. In that role he worked to better connect student support systems across grade levels, ensuring that students’ individual needs followed them from elementary to middle to high school. While challenging, he said the work taught him to “remember the human element of every decision you make.”
Since becoming Superintendent, Simmons has reflected that person-first passion onto school personnel. He believes the district has made meaningful progress in its pursuit of creating a positive, inclusive environment for teachers, administrators, central office employees, and support staff. “We were in a low spot,” Simmons admitted, “We are in a much better spot with retaining folks and a better spot with hiring.” He said the district has worked hard to keep CCPS staff feeling motivated and heard through increased attention to employee feedback, expanded opportunities for advancement, and improvements to wages and benefits.
Under Simmons’ leadership, CCPS has also tackled long-standing structural challenges. Among them was aligning staff contracts – an issue that had persisted for more than a decade. Resolving it allowed all employees to begin the school year together, which Simmons said has strengthened the feeling of community among staff members and has bolstered communication across the school system.
Academically, Simmons hopes to build upon an already-impressive foundation of student performance. As for the 24 counties in Maryland, “We consistently rank around 23rd out of 24 in terms of wealth, our wealth in terms of dollars,” Simmons said, noting that Caroline County is “wealthy in people.” Yet, state testing data shows that CCPS students consistently exceed what is expected of them because of this statistic. “There's a tremendous amount of research out there that will tell you that your zip code and the wealth that exists within that area is a strong predictor in academic success, and the research is accurate in most cases. But for a county whose wealth is historically next to last in the state, we have consistently outperformed where we should be,” he said, “ I absolutely love that our lack of fiscal resources does not define anything about our kids and our families.”
But while the numbers are better than average, they are not perfect, and Simmons says there is still work to be done. “We need to improve our academic outcomes,” he said, emphasizing goals such as increasing reading proficiency by early grades, strengthening math performance, and reducing dropout rates. “If we say all kids, it’s got to mean all kids.”
Looking ahead, Simmons’ priorities for the next four years build directly on these key pieces of the public school system puzzle.
First, “we cannot go backwards” in staff wellbeing. Continued focus on voices of employees, professional growth, and workplace satisfaction will remain central to the district’s success, he said.
Second, the district is preparing for major facility investments, most notably the long-anticipated replacement of Lockerman Middle School. With a hopeful completion timeline of August 2029, Simmons emphasized that staying on track is critical, not just for current students, but for future building projects across the county. Denton Elementary School, North Caroline High, the Caroline Career and Technology Center, Ridgely Elementary, and Federalsburg Elementary are all due to be rebuilt or renovated in the coming years (though not necessarily in that order). Delays now, Simmons said, could create ripple effects for decades.
Third, academics will remain at the forefront. With significant changes coming from the state, including new standards, assessments, and instructional frameworks, the district has reorganized its leadership structure to ensure a strong focus on teaching and learning. Simmons noted that he goal is not only to keep pace with those changes, but to use them as an opportunity to improve outcomes for students. “If we give ourselves a goal of less than, it means we're okay with saying some fail, and you just can't. You can't give yourself a goal that allows you to say it's okay that some kids can be forgotten,” he said.
Finally, Simmons is focused on expanding pathways that prepare students for life after graduation. Whether through career and technical education, dual enrollment, or partnerships with local businesses, he wants every student to leave the system “career ready.” That includes opportunities to earn industry credentials and gain real-world experience before graduating.
Underlying all of these priorities is a long-term mindset. Simmons often describes it as the difference between quick fixes and sustained growth. “If you know something is right, you pour into it,” he said, “You can either plant a seed, water it, watch it take its time and understand progress might be messy… or you can jump to the latest fad, the new shiniest toy. We’ve tried to stay with what we know works and pour into the right things.”
