The Middle School years are some of the most formative in a student’s educational journey, and Stratford’s Middle School experience is intentionally designed for the academic, social, and emotional growth that defines this important stage of development. As Stratford looks ahead to the 2026-2027 school year, the school is excited to strengthen the leadership structure around students while preserving the daily experience, relationships, routines, and sense of belonging that define these years.

Middle School will continue to have its own identity, traditions, programming, expectations, advisory experiences, and student life opportunities. Students will continue to be known by their teachers, supported by trusted adults, and guided through the academic, social, and emotional growth that makes Middle School such an important season.

What is changing is the team surrounding each student. This enhanced leadership model is designed to provide more adult touchpoints, clearer grade-level communication, stronger student advocacy, and greater consistency across classrooms, expectations, and the overall student experience.

MEET OUR GRADE-LEVEL DEANS

At the center of this enhanced model is the introduction of grade-level deans under the direction of our Assistant Head for Student Life (6-12), Coach Jarvis Smith. The Grade-Level Dean structure was introduced in the Upper School for the 2025-2026 school year and has provided strong, consistent support for students, teachers, and families. Expanding the model to Middle School allows Stratford to provide more focused, grade-level attention during some of the most important years in a student’s development.

Deans will serve as the closest administrative point of connection for students and families. They will support students’ academic and social-emotional growth, help them navigate challenges, celebrate their successes, and partner with teachers to address concerns early. For families, Deans provide an additional layer of communication, clarity, and partnership between home and school. 

The faculty members serving as Middle School Grade-Level Deans for the 2026-2027 school year bring over 50 years of combined teaching experience, including 30 years at Stratford, demonstrating deep familiarity with Stratford’s Middle School.

Sixth Grade Dean: Natalie Barrett
Mrs. Natalie Barrett has taught fifth through seventh grade science at Stratford for the past five years. She has also served as Science Olympiad coach for the past four years and advised the newly established House of Officium this year. Her experience with students at the beginning of their Middle School journey will help provide steady support as sixth graders build confidence, independence, and a stronger sense of belonging. She is especially looking forward to building relationships with students and “guiding them to reach their full potential.” 

Seventh Grade Dean: Nancy Gordillo
Mrs. Nancy Gordillo brings 33 years of teaching experience to this role, including 17 years as a trusted presence in Stratford’s Middle School. Beyond the classroom, she has invested in students through Quiz Bowl, Student Council, and as Middle School chess coach and moderator. She is especially excited to serve as Seventh Grade Dean because she sees seventh grade as an important year of “maturing and self-discovery.” As Gordillo shared, “I look forward to building strong connections with our 7th graders during this important stage of growth… guiding and supporting them as they navigate both academic and personal challenges.” 

Eighth Grade Dean: Adair Brown
Mrs. Adair Brown brings a broad perspective to her role as Eighth Grade Dean, with experience teaching students from Middle School through Upper School. During her 14 years in education, including eight years at Stratford, she has taught mathematics across grades six through twelve and Middle School science, while also serving in leadership roles as an instructional coach, Mathematics Department Chair, and disciplinarian. She is looking forward to “helping students transition during a challenging time… as they begin to grow into greater independence” and prepare for Upper School. 

 

STONGER ALIGNMENT, DISTINCT MIDDLE SCHOOL EXPERIENCE

Supporting the grade-level deans is a broader leadership structure designed to strengthen alignment across Middle and Upper School without changing the distinct daily experience of Middle School. Ms. Anna Dejdar will expand her role from Head of Upper School to Head of Middle and Upper School, supported by Mr. Stephen O’Hara as Assistant Head for Academics, 6–12, and Coach Jarvis Smith as Assistant Head for Student Life, 6–12. Middle School student life programs will continue to be led by Middle School faculty so traditions, relationships, and student experiences remain rooted in the division. 

Anna Dejdar- Head of Middle and Upper School
Ms. Anna Dejdar brings 18 years in education, including 11 years in administration, with experience spanning both student support and academic leadership. She holds a Master of Science in Educational Leadership and a Master of Science in School and Mental Health Counseling from the University of Pennsylvania, grounding her work in both strong leadership practice and a deep understanding of student development. She has two years of Middle School experience and is currently in her second year at Stratford as Head of Upper School. Prior to Stratford, Anna served at The Shipley School as Associate Head of Upper School for Student Life, 11th and 12th Grade Dean, PAIS Accreditation Chair, and Director of Research.

Ms. Dejdar’s leadership is rooted in building meaningful relationships, creating systems that support students and faculty, and ensuring that each student is known, guided, and challenged to grow. As Dejdar shared, “Middle School is such an important and formative stage of development, and I have always loved working with students at this age– their curiosity, energy, and growth during these years are remarkable. I am deeply committed to ensuring that students across both divisions feel known, challenged, and supported as they grow.”

Jarvis Smith – Assistant Head for Student Life, 6–12
Coach Jarvis Smith will serve as Assistant Head for Student Life, supporting students across grades six through twelve. In this role, he will lead work related to discipline, school culture, advisory, extracurricular involvement, student engagement, and grade-level leadership.

Coach Smith brings more than 22 years of experience in education, including more than a decade working directly with Middle School students. His experience as a teacher, coach, Dean of Students, and Assistant Athletic Director, along with his current work in student engagement, discipline systems, and community-building, positions him to support a strong and positive student life experience across divisions.

At the 2026 Yearbook Dedication Ceremony, senior Ben Kelly described Coach Smith as “a positive force in the school and a smiling face in the hallway.” From checking in on students to helping solve problems and planning events that bring the student body together, Coach Smith’s presence is felt across campus.

As Kelly shared, “He seems to always be there with a fist bump or a pat on the back whenever you need it most. This supportive energy makes waves in the community and affects everyone.”

Stephen O’Hara – Assistant Head for Academics, 6–12
Mr. Stephen O’Hara will serve as Assistant Head for Academics, guiding academic systems across grades six through twelve. He will focus on curriculum, classroom expectations, student progress, academic communication, and systems that help teachers and families identify student needs early. 

O’Hara will begin his 10th year at Stratford and brings extensive experience as a teacher, department chair, and administrator. He has taught a wide range of Upper School courses, including AP classes, and has led key academic systems that support student progress and communication.

One of the systems he is especially excited to bring more fully into the Middle School experience is the Academic Progress Report system. “This system allows us to track student progress closely, identify trends, respond proactively, and ensure a high level of teacher-parent communication,” O’Hara shared. “Those reports are part of a larger support network, including deans who meet regularly to discuss student progress and map strategies for intervention.”

This approach allows for earlier identification of needs and more coordinated support for students. 

SUPPORT, STRUCTURE, AND CONNECTION

Together, this enhanced leadership structure adds more direct support around Middle School students while preserving the identity, relationships, and daily experience that make Stratford’s Middle School distinct. Grade-level deans will provide focused attention at each grade level, while the 6–12 academic and student life leadership structure will strengthen communication, consistency, and coordination across divisions.

For students, this means more trusted adults working together to guide their growth. For families, it means clearer communication and a more connected support system. For teachers, it means additional partnership in helping students succeed. 

At every level, the goal remains the same: to ensure each Middle School student is known, challenged, and supported at every step of their Stratford journey.