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.

Duties and Responsibilities

Academic Leadership

• 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 practices.
  
  

Faculty and Staff Support

• 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.

Student Life and Community Culture

• 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.
  
  

School Operations and Administration

• 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 engaging, mission-aligned auxiliary and summer experiences that serve both current families and the broader community.

Family and Community Engagement

• Communicate effectively and compassionately with families, building trust and partnership.
• Participate in admissions, retention, and community outreach efforts as appropriate.
• Represent Pine Cobble School professionally within the local and broader independent school community.
• Serve as a liaison for the Parent Teacher Group (PTG) supporting their efforts to build community among Pine Cobble families, support school initiatives, and participate in the events of our broader community in the Northern Berkshires.

Strategic Leadership

• Contribute to long-range planning and school improvement initiatives.
• Assume leadership responsibilities as delegated by the Head of School and serve as acting Head when needed.
  
  

Skills and Qualifications

• Bachelor’s degree required; advanced degree in education or related field preferred.
• Significant experience as an educator and educational leader, preferably in an independent school setting.
• Demonstrated commitment to progressive education, experiential learning, and child-centered pedagogy.
• Strong interpersonal, communication, and organizational skills.
• Experience supervising and supporting faculty.
• Deep commitment to diversity, equity, inclusion, and belonging.
• Commitment to life-long learning as demonstrated by ongoing professional development and advancement in the field of education and best practices in all aspects of the work.
• Experience creating and sustaining an inclusive school culture and environment.
• Experience managing budgets in support of the financial and strategic priorities of the school

Personal Attributes

• Collaborative, reflective, and approachable leadership style.
• High level of integrity, professionalism, and emotional intelligence.
• Ability to balance strategic thinking with practical, day-to-day problem solving.
• Enthusiasm for working with children and adults in a close-knit school community.
• Strong interpersonal, facilitation, and communication skills, including the capacity to listen to many voices.
• Sound judgement in managing daily personal and interpersonal concerns calmly, compassionately, and with discretion.
• A sense of humor, warmth, and a willingness to bring joy to the work.

About Pine Cobble School

Pine Cobble is an all gender preschool through grade eight day school in Williamstown, MA. Our mission is to cultivate in each student a lifelong passion for learning, a strong sense of self-worth, and respect for others throughout the community. These goals are achieved through robust programming featuring a variety of academic and elective offerings, frequent outdoor engagement, cross grade-level activities and events, frequent community-wide gatherings, and off-campus experiences.

Connections working at Pine Cobble School