At their June meeting, the Caroline County Board of Education appointed Dr. Robert W. Willoughby Director of Administrative Services effective July 1.
Superintendent Derek Simmons explained that this position and two other administrative appointments on the June agenda are position-neutral and the result of reorganizing existing positions. “This particular move is in preparation for upcoming financial operation changes required by the State,” he said. He shared that in order to streamline and support that work, Dr. Willoughby’s current position is being expanded to include finance department roles that pertain to human resources, such as payroll and benefits, as well as day to day financial operations. This change will enable the Chief Financial Officer and staff to focus on strictly budget development and management, as well as strategic planning and forecasting as the Blueprint changes our current practices.
Dr. Willoughby has served as Supervisor of Human Resources since 2022. He began his career with Caroline County Public Schools as a Social Studies teacher at Colonel Richardson High School in 2002. In 2011, he was appointed assistant principal at Lockerman Middle School, followed by a move to North Caroline High School in 2015, also as assistant principal. He was subsequently appointed principal at Colonel Richardson Middle School in 2017 where he served until coming to the Central Office as a Supervisor of Instruction, overseeing Social Studies, World Languages, Financial Literacy, Policy Development and Athletics.
Dr. Willoughby is a graduate of Colonel Richardson High School. He attended college at Washington College and North Central University earning a Bachelor of Arts in History and Political Science, a Master of Arts in History, and a Master of Education in Athletic Administration. He holds a Doctorate of Public Administration from West Chester University.
Dr. Willoughby served six years on the Governor’s P-20 Leadership Council and in leadership roles with the Administrators and Supervisors Association of Caroline County. He is also a past president with the Maryland Association of Secondary School Principals.