Assistant Head of Upper School

Wellington School seeks an Assistant Head of Upper School to lead in a division known for an innovative, ambitious, and student-centered approach to learning. Working in close partnership with the Head of Upper School, the Assistant Head is the division’s lead for student life. The Assistant Head will oversee the Grade Level Dean team, setting the direction for the advisory, assembly, and grade-level programs, while steering student conduct, student government, clubs, and beloved community traditions. This person will be key to the success of the division and a champion for all elements of the Upper School.

This is a role for an educator who wants to work creatively and collaboratively in a dynamic division at an exciting time for our Upper School. The Assistant Head will manage and iterate systems, coach a team, and shape how every Upper School student is known, supported, and challenged. The role is well-suited to someone who is excited to lead at the division level, take ownership of programs, and help build the best Upper School imaginable alongside colleagues who share a passion for academic excellence and exceptional outcomes for graduates who put knowledge into action to improve our world.

Supervisory Responsibilities

· Supervises and coaches four Grade Level Deans, building a collaborative and effective student support team.

· Oversees the Upper School advisory system, setting expectations, providing training, and supporting advisors in fulfilling their roles.

Key Responsibilities

Student Culture and Belonging

· Cultivates a joyful, inclusive, and spirited Upper School culture, grounded in kindness and mutual respect, in which students feel known, valued, and proud to belong.

· Strengthens community and school spirit through Morning Meeting, assemblies, celebrations, and the daily life of the Upper School.

· Collaborates on 8th-to-9th grade transition and onboarding for new Upper School students, in partnership with the Middle School and Admissions, fostering early connections.

Student Life, Leadership, and Voice

· Leads a vibrant and evolving student life program, including Student Council, clubs, and student organizations.

· Partners with faculty advisors and student leaders to keep activities engaging, accessible, and responsive to student interests.

Student Support and Community Expectations

· Leads the division’s approach to student conduct: sets clear expectations, handles disciplinary matters fairly and consistently, and uses restorative practices to help students take responsibility and repair relationships.

· Partners with counselors, learning specialists, and faculty to identify and support students facing academic, social, emotional, or behavioral challenges.

· Communicates clearly, compassionately, and promptly with families about conduct and student well-being, including in difficult conversations.

· Reviews and recommends updates to the Upper School section of the student handbook.

Divisional Leadership and Operations

· Serves on the Upper School leadership team and contributes to strategic planning and priorities.

· Serves as a key thought partner with the Head of Upper School in setting a divisional vision.

· Shares responsibility for daily operations and acts as Head of Upper School when required.

· Represents the Upper School at admissions events, family programs, and school-wide functions.

Teaching

· Teaches up to two year-long Upper School courses each year.

Required Skills & Abilities:

Connecting with Students

· A genuine love of adolescents and enthusiasm for participating fully in the daily life of a school.

· A keen ability to connect with teenagers, earn their trust, and understand their perspectives.

· The ability to balance warmth and approachability with high expectations, clear boundaries, and sound judgment.

Building Community and Student Leadership

· Creativity, energy, and initiative in designing engaging student experiences, building traditions, and bringing new ideas to life.

· A demonstrated commitment to joy, belonging, and school spirit, and skill in empowering student leaders and helping young people translate their ideas into action.

· Culturally competent and inclusive, with a deep respect for diverse perspectives and backgrounds.

Student Conduct and Family Partnership

· Proven ability to manage and resolve student behavior issues using positive discipline and restorative practices.

· Exceptional interpersonal and communication skills, both verbal and written, with the ability to build trust with students, faculty, and families, including through sensitive conversations and conflict resolution.

Leadership and Organization

· Skilled in strategic thinking and problem-solving, with the ability to balance immediate needs with long-term goals.

· Proactive capacity to bring ideas and needs to life with a determined spirit.

· Strong organizational and time-management skills, with the ability to prioritize multiple responsibilities in a fast-paced environment.

· Collaborative and team-oriented, and technologically proficient with educational tools, learning platforms, and administrative systems.

Education & Experience:

· Bachelor’s degree required; master’s degree in education, educational leadership, or a related field strongly preferred.

· Deep understanding of adolescent development and social-emotional learning, including the skills, relationships, and experiences that prepare students for independence and adulthood.

· A record of designing, leading, or strengthening advisory, student life, leadership, or extracurricular programs.

· Experience supervising, training, or coaching adults, including faculty coaching.

· Experience with restorative practices, community-building, and keeping families as partners through hard conversations.

Physical Requirements:

· Frequent movement between classrooms, offices, and common spaces throughout the campus, including up and down stairs.

· Occasionally required to lift or move objects up to 30 pounds. (e.g., teaching materials, classroom furniture, event supplies).

· Regular bending, kneeling, squatting, and sitting on the floor to engage with young children at their level.

· Visual and auditory ability to monitor student safety and respond to needs.

· Ability to move quickly in emergency situations and remain calm under pressure.

· Must be available for occasional after-school or evening professional development or events.

· Must be able to work effectively in a busy and sometimes noisy classroom environment, maintaining focus and clear communication with students and colleagues.

All candidates should include a resume and cover letter.