Assistant Head of School

Pine Cobble School, an independent Beginner through Grade 8 school rooted in progressive education and experiential learning, seeks a dynamic and collaborative Assistant Head of School. Reporting directly to the Head of School, the Assistant Head plays a central leadership role in advancing the school’s mission, supporting academic excellence, nurturing a strong faculty culture, and ensuring that the daily life of the school reflects Pine Cobble’s values.

Job Summary

The Assistant Head of School is a highly visible leader who works closely with faculty, students, families, and administrators. This role blends strategic leadership with hands-on engagement in teaching and learning, school operations, and community life. The Assistant Head of School serves as the key point person for faculty regarding all manner of school-related responsibilities, helping to anticipate and address challenges.

They will oversee student support plans, faculty professional growth and development, and community partnerships.

Pine Cobble School is committed to equity and justice. Indeed, we have made this a core priority in our strategic plan. This work is critically important — for all of our students, for our institution, and for the world that our students will someday lead. We approach our work and learning with care and compassion for each other, ourselves, the greater community, and our natural environment.

We strive to create an effective learning environment that engages learners and supports their unique learning styles, allowing them to acquire new skills in a way that maximizes understanding and retention.

• Partner with the Head of School and Dean of Academics to provide vision and leadership for curriculum, instruction, and assessment aligned with Pine Cobble’s mission and educational philosophy.
• Partner with the Director of Human Resources and the Head of School in the hiring and onboarding of faculty.
• Support and supervise faculty, including mentoring, evaluation, and professional growth.
• Lead and coordinate the faculty evaluation process in collaboration with the Head of School, Dean of Academics, and Senior Advisor/Mentor Teacher, ensuring clear expectations, consistent practices, constructive feedback, and alignment with school values.
• Lead our IDEA (Inclusiveness, Diversity, Equity, and Action) committee and support Pine Cobble’s commitment to examining and deepening inclusiveness and equity in both our community and curricula. Ensure intellectual inquiry increasingly reflects and considers broad perspectives and cultures.
• Collaborate with teachers to ensure coherence and continuity across grades.
• Promote inclusive, developmentally appropriate, and student-centered teaching practice.

• Foster a collegial, reflective, and growth-oriented professional culture.
• Lead or support faculty meetings, professional development initiatives, and onboarding of new faculty.
• Serve as a trusted resource for teachers, offering coaching and problem-solving support.
• Coordinate ongoing training for faculty around issues of diversity, equity, and implicit bias via faculty professional development days.

• Support a positive, respectful, and inclusive school climate for all students.
• Collaborate in student support processes, including social-emotional learning and behavioral guidance.
• Maintain a visible presence in classrooms, common spaces, and school events.
• Support after-school special events and activities for students.
• Coordinate and oversee annual celebratory traditions, such as Graduation and Recognition Day.

• Assist in the day-to-day operations of the school, ensuring smooth and effective systems and routines.
• Support scheduling, coverage, and coordination across academic and operational functions.
• Partner with the Head of School on policy development, implementation, and review.
• Provide leadership and oversight for Pine Cobble School’s auxiliary programming, including after-school offerings, enrichment programs, and special initiatives.
• Collaborate with the Director of Auxiliary Programs to design…