Kyle Bentley is a passionate and accomplished educational leader with more than 15 years of experience serving students, families, and school communities across Pennsylvania and Delaware.

Mr. Bentley began his career as a first, third, and fifth 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. He subsequently served as an assistant principal at Seaford High School, W.T. Chipman Middle School, and Cape Henlopen High School. His leadership was recognized in 2020 when he was named the State of Delaware Assistant Principal of the Year. Before joining Sussex Academy as Head of School in 2024, Mr. Bentley served as principal of H.O. Brittingham Elementary School in the Cape Henlopen School District.

A lifelong learner, Mr. Bentley believes strongly in the transformative impact of a high-quality education. He graduated from Mercyhurst Preparatory School in Erie, Pennsylvania, and earned both his bachelor’s degree in kindergarten and elementary education and his master’s degree in curriculum and instruction with an emphasis in educational leadership from Penn State University. He has also completed doctoral coursework in educational leadership at the University of Delaware.

As a bilingual educator with leadership experience spanning elementary, middle, and high school settings, Mr. Bentley brings a K–12 perspective to building strong schools and creating opportunities for every student to succeed. Throughout his career, he has focused on developing high performing teams, strengthening instructional practices, building authentic relationships, and creating systems that support continuous improvement. He believes the strongest schools are built through collaboration among students, educators, families, and community partners around a shared commitment to student success.

As Head of School, Mr. Bentley is committed to advancing Sussex Academy’s vision to become the premier K–12 school system in Delaware. Guided by the school’s mission to create a supportive school environment with accelerated learning opportunities that prepare students to explore, experience, and excel, his leadership is focused on strengthening academic excellence, expanding opportunities for students, investing in exceptional educators, and building a connected K–12 school community prepared for the future.

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