Current Assistant Principal of the Year

(Rob Willoughby receives his APOY plaque from MASSP Executive Director Scott Pfeifer)

Mr.Robert Willoughby, NBCT, is an assistant principal at North Caroline High School in Caroline County, Maryland.  A product of Caroline County Public Schools, Rob went on to attend Washington College in Chestertown, Maryland, earning a Bachelors of Arts in History and Political Science.  Rob also holds a Masters of Arts in History from Washington College as well as a Masters of Education from NorthCentral University.  He was awarded certification by the National Board of Professional Teaching Standards in 2009 and is currently pursuing a doctorate in Public Administration from West Chester University. 

Rob started his career in education at Colonel Richardson High School as a history and government teacher from 2002-2011, as well as serving as a coach, class advisor and sponsor for various clubs including the Student Government Association and the National Honor Society.   In 2011, he was appointed Assistant Principal of Lockerman Middle School in Denton and in 2015 was appointed Assistant Principal of North Caroline High School in Ridgely.  Since 2010, he has coached Parliamentary Procedure teams for both Colonel Richardson and North Caroline FBLA chapters, with each team qualifying for competition at the national level.  In 2015, Rob was part of the second cohort of the Governor’s Promising Principal’s Academy.  Rob also serves as the President of the Caroline County Administrators and Supervisors Association (ASACC) and in 2015 was appointed by Governor Hogan to serve on the Governor’s P-20 Leadership Council.  

Outside of school, Rob is active in his community and church, serving in various community service clubs.  Rob serves on the Board of Directors of CARCO Federal Credit Union and is a member of the Ethics Commission for the Town of Federalsburg.  He enjoys golf, traveling and is an avid Baltimore Ravens fan.