Assistant Head of School

Greenwich Country Day School is an independent, co-educational day school with a current enrollment of over 1400 students in grades N-12, and a faculty and staff of over 350. The original Old Church Road campus is home to grades N-8. The High School, established in 2019, is located less than two miles away on Stanwich Road. Founded in 1926, Greenwich Country Day School is a family school where innovative teaching is encouraged as teachers model and foster a love of learning, challenge and inspire children toward academic excellence, and cultivate students’ interests and talents outside of the classroom.

We value purposeful and personal learning in a joyful environment, with emphasis on the development of character, creativity, and a sense of personal value, along with strong academic skills. GCDS is committed to graduating ethical, confident leaders who possess a strong sense of purpose.

Greenwich Country Day School seeks an Assistant Head of School to start on July 1, 2026.

The Assistant Head of School is a senior academic and community leader responsible for ensuring coherence, alignment, and excellence across the Nursery–Grade 12 program at Greenwich Country Day School. Working across all three campuses (Stanwich, Old Church Rd, and French Farm), this leader connects academics, arts, athletics, and co-curricular life to student growth and the Portrait of a Learner. The Assistant Head supports faculty and administrators, champions student thriving, and partners closely with families.

In partnership with the Head of School and the Senior Administrative Team, this role maintains program integrity, strengthens adult learning, and helps shape a school culture grounded in belonging and whole-child development.

The Assistant Head oversees the vertical articulation and delivery of the academic program, ensuring coherence across divisions and campuses (Stanwich, Old Church Road, French Farm) so that students experience GCDS as one unified school. This includes guiding curricular integrity, maintaining academic records and structures, and supervising experiential learning such as trips to ensure alignment with mission, developmental readiness, and equitable access.

With a strong presence in classrooms and community life, the Assistant Head helps build continuity of experience and clarity of purpose for students and faculty alike.

This role is central to the growth and development of faculty. The Assistant Head supports administrators, coaches, evaluates teachers, and designs strategic professional learning that builds capacity and nurtures reflective instructional practice. By leveraging both internal expertise and external partnerships, this leader creates systems that promote collaboration, innovation, and the continuous elevation of teaching and learning across the school.

As a visible and collaborative member of the senior leadership team, the Assistant Head works closely with the Head of School to foster clarity, cohesion, and shared ownership of priorities. This leader facilitates the work of the administrative team, supports communication across divisions, and regularly advises on emerging opportunities within the program. The Assistant Head represents the school in both internal and external contexts.

The Assistant Head connects vision to execution by aligning people, systems, and resources with institutional priorities. Responsibilities include managing the academic program budget in partnership with the Director of Finance, leveraging data to inform decision-making, and contributing to long-range planning. The Assistant Head plays an active role with the Board of Trustees Strategy Committee and helps build the adaptive structures necessary for thoughtful, mission-driven innovation.

The Assistant Head serves as a unifying force across the three campuses, nurturing a “one school” identity grounded in consistent expectations, shared purpose, and a common student experience. This leader…