Kyle Bentley is a passionate, focused and accomplished leader with more than 15 years of experience. 

Mr. Bentley began his career as a 1st, 3rd, and 5th grade teacher at Julia de Burgos Bilingual Elementary School in the School District of Philadelphia. In 2013, he moved to Sussex County to begin his administrative career through the Delaware Leadership Project, and subsequently served as an assistant principal at Seaford High School, W.T. Chipman Middle School and Cape Henlopen High School. His dedication and leadership were recognized in 2020, when he was honored as the State of Delaware Assistant Principal of the Year. Before joining Sussex Academy in 2024, Mr. Bentley was principal of H.O. Brittingham Elementary School in the Cape Henlopen School District.  

Mr. Bentley is a lifelong learner that understands the importance of a high-quality education. He graduated from Mercyhurst Preparatory School in Erie, Pa., and earned his bachelor’s degree in kindergarten and elementary education and his master's degree in curriculum and instruction with an emphasis on educational leadership from Pennsylania State University. Additionally, he completed coursework from the University of Delaware towards his Ed.D in educational Lleadership.

As a bilingual educator with K-12 experience, he understands the importance of working with teams to design and implement strategies to achieve success for every student. His experience leading a variety of educational settings have provided him with the unique opportunity to lead alongside the best educators in Delaware and throughout the country. Most importantly, he thrives on working collaboratively with students, staff, teachers, families and community partners to build a brighter and better future for the students he serves. 

Mr. Bentley is deeply committed to maintaining and advancing the high standards of academic excellence and community engagement that Sussex Academy is known for across the state. The Sussex Academy charter promise to “Explore - Experience - Excel” and our mission to foster academic achievement and social responsibility in a small school setting will guide his leadership as the Head of School.

On a personal note, Kyle and his wife are proud to be raising their two daughters in the community and enjoy surf fishing on the beach, traveling and spending time with friends.