Welcome Rob Orlando - Our Next Head of School
With nearly thirty years of educational leadership experience, Rob brings warmth, vision, and a deep commitment to the values that define St. Anne’s Episcopal School. His tenure begins July 1, 2026.
Introduction
St. Anne’s Episcopal School is delighted to announce the appointment of Rob Orlando as our next Head of School, beginning July 1, 2026.
Rob brings nearly thirty years of experience in both public and independent education. His leadership style—rooted in collaboration, compassion, and curiosity—reflects the very qualities we seek to nurture in our students.
A lifelong educator, Rob is known for cultivating vibrant learning communities where every student is known, valued, and inspired to grow.
Rob’s Background and Leadership
I am thrilled to be joining St. Anne’s as your next Head of School. My family and I are excited to become part of such a welcoming and supportive community. Together, we’ll honor what makes St. Anne’s special while identifying new opportunities for growth, innovation, and connection. -- Rob Orlando
Meet the Orlando Family
Originally from the Philadelphia area, Rob and his wife, Karen, have been married for twenty-seven years and are the proud parents of four children—Donald, Samantha, Vita, and Stella. The Orlando family looks forward to relocating to Delaware and becoming active members of the St. Anne’s and Middletown communities.
Our Shared Values
Rob’s philosophy of education aligns deeply with St. Anne’s Episcopal identity, where respect, responsibility, and compassion guide every interaction. His leadership will continue our mission to ensure every child is known, nurtured, and challenged to lead a life of purpose.
Our Herons explored nature’s classroom right on campus — walking between tall corn stalks that surround St. Anne’s. This rare moment, possible only once every few years when the fields are in cycle, reminds us how deeply learning is rooted in the land we call home.
During our Founders’ Day Chapel, Mrs. Bennett reflected on the faith, courage, and collaboration that shaped St. Anne’s from the very beginning. Her message invited our community to carry that same purpose forward as we continue to grow together.
Students and parents came together to celebrate Diwali, designing a vibrant rangoli that symbolized unity, creativity, and joy. The day shined brightly with color, laughter, and cultural appreciation — a true reflection of our diverse and caring community.
About St. Anne’s Episcopal School
Founded in 2002, St. Anne’s is a Preschool–8th Grade independent school in Middletown, Delaware. Guided by our Episcopal mission, we prepare students to be known, nurtured, and challenged through academic excellence, spiritual growth, and compassion.