{"22152619":{"jobPath":"/jobs/22152619/vice-principal-of-grades-9-12","source":"naylor","job":"22152619","jobTitle":"Vice Principal of Grades 9-12"},"22152471":{"jobPath":"/jobs/22152471/journalism-and-media-studies-coordinator","source":"naylor","job":"22152471","jobTitle":"Journalism and Media Studies Coordinator"},"22152692":{"jobPath":"/jobs/22152692/middle-school-stem-lead-teacher","source":"naylor","job":"22152692","jobTitle":"Middle School STEM Lead Teacher"},"22152676":{"jobPath":"/jobs/22152676/business-manager","source":"naylor","job":"22152676","jobTitle":"Business Manager"},"22152511":{"jobPath":"/jobs/22152511/dean-of-students-residential-life","source":"naylor","job":"22152511","jobTitle":"Dean of Students & Residential Life"},"22152597":{"jobPath":"/jobs/22152597/per-diem-athletic-trainer","source":"naylor","job":"22152597","jobTitle":"Per Diem Athletic Trainer"},"22152613":{"jobPath":"/jobs/22152613/lower-school-associate-teacher-1st-and-2nd-grade","source":"naylor","job":"22152613","jobTitle":"Lower School Associate Teacher: 1st and 2nd Grade"},"22152735":{"jobPath":"/jobs/22152735/humanities-faculty-english-emphasis","source":"naylor","job":"22152735","jobTitle":"Humanities Faculty - English emphasis"},"22152435":{"jobPath":"/jobs/22152435/athletic-director-programs-manager-2026-2027","source":"naylor","job":"22152435","jobTitle":"Athletic Director & Programs Manager 2026-2027"},"22152634":{"jobPath":"/jobs/22152634/learning-support-specialist","source":"naylor","job":"22152634","jobTitle":"Learning Support Specialist"},"22152717":{"jobPath":"/jobs/22152717/assistant-athletic-director","source":"naylor","job":"22152717","jobTitle":"Assistant Athletic Director"},"22152715":{"jobPath":"/jobs/22152715/humanities-faculty-history-social-studies-emphasis","source":"naylor","job":"22152715","jobTitle":"Humanities Faculty (History/Social Studies Emphasis)"},"22152737":{"jobPath":"/jobs/22152737/early-ed-elem-student-support-coordinator","source":"naylor","job":"22152737","jobTitle":"Early Ed & Elem Student Support Coordinator"},"22152641":{"jobPath":"/jobs/22152641/teaching-fellow-2026-2027-academic-year","source":"naylor","job":"22152641","jobTitle":"Teaching Fellow (2026-2027 Academic Year)"},"22152740":{"jobPath":"/jobs/22152740/middle-school-global-studies-teacher","source":"naylor","job":"22152740","jobTitle":"Middle School Global Studies Teacher"},"22152646":{"jobPath":"/jobs/22152646/key-middle-school-language-comprehensive-teacher","source":"naylor","job":"22152646","jobTitle":"Key Middle School Language Comprehensive Teacher "},"22152647":{"jobPath":"/jobs/22152647/lower-middle-school-library-media-specialist","source":"naylor","job":"22152647","jobTitle":"Lower & Middle School Library Media Specialist "},"22152688":{"jobPath":"/jobs/22152688/outdoor-education-faculty-and-coordinator","source":"naylor","job":"22152688","jobTitle":"Outdoor Education Faculty and Coordinator"},"22152568":{"jobPath":"/jobs/22152568/music-educator-primary-school-gr-1-5","source":"naylor","job":"22152568","jobTitle":"Music Educator, Primary School (Gr. 1-5)"},"22152744":{"jobPath":"/jobs/22152744/middle-school-learning-specialist","source":"naylor","job":"22152744","jobTitle":"Middle School Learning Specialist"},"22152607":{"jobPath":"/jobs/22152607/school-counselor","source":"naylor","job":"22152607","jobTitle":"School Counselor"},"22152648":{"jobPath":"/jobs/22152648/middle-school-lead-teacher-grade-7-8-language-arts","source":"naylor","job":"22152648","jobTitle":"Middle School Lead Teacher: Grade 7 & 8 (Language Arts)"},"22152549":{"jobPath":"/jobs/22152549/assistant-volleyball-coach","source":"naylor","job":"22152549","jobTitle":"Assistant Volleyball Coach"},"22152527":{"jobPath":"/jobs/22152527/history-social-science-teacher","source":"naylor","job":"22152527","jobTitle":"History/Social Science Teacher"},"22152528":{"jobPath":"/jobs/22152528/english-teacher","source":"naylor","job":"22152528","jobTitle":"English Teacher"}}
Position Summary Canterbury School seeks an exceptional, highly experienced, student-centered leader to serve as Schoolwide Dean of Students and Restorative Practices. This is a senior, community-facing role responsible for ensuring that student culture, conduct, attendance, and accountability systems are coherent, consistent, and mission-aligned from our youngest learners through graduation—while maintaining a sustained, visible, day-to-day leadership presence in the Middle and Upper School.
The Dean will lead a restorative approach to school culture: proactively building community and belonging; responding to harm and conflict with practices that repair relationships and strengthen responsibility; and ensuring that accountability is real, timely, and educational rather than purely punitive. The Dean will also own attendance as a primary schoolwide focus, ensuring accurate tracking, early intervention, family partnership, and consistent enforcement of handbook expectations.
This role requires expert judgment, superb communication skills, strong operational competence, and deep fluency in restorative practices and adolescent development. The Dean will coach adults, partner with families, and build systems that improve follow-through—so expectations and policies are not merely written, but lived.
Core Responsibilities
Schoolwide Restorative Practices Leadership
Serve as the School’s lead architect and implementer of restorative practices PK–12, ensuring developmentally appropriate practices across divisions (Early Childhood/Lower School foundations; Middle/Upper School depth and repair).
Design and lead a multi-tiered restorative framework that includes proactive community-building practices (Tier 1) and responsive practices when harm occurs (Tier 2/3), with clear referral pathways and facilitation protocols.
Facilitate (and build internal capacity to facilitate) restorative circles, conferences, mediations, reentry meetings, and restorative agreements.
Train, coach, and support faculty and staff in restorative language, de-escalation aligned to restorative principles, consistent adult responses, and high-expectations/high-support practices.
Establish fidelity expectations and practical tools (scripts, question sets, documentation templates, response menus) so restorative practice is consistent across classrooms, hallways, athletics, and common spaces.
Middle and Upper School Student Culture, Conduct, and Accountability
Serve as the primary leader for student conduct, culture, and community accountability in the Middle and Upper School.
Lead investigations, decision-making, and restorative responses for student behavior incidents, in collaboration with division leadership and counselors as appropriate.
Ensure fair, consistent, and well-documented application of handbook expectations, with attention to student dignity, equity, and developmental appropriateness.
Support advisors/grade-level leads with structured guidance for addressing recurring behavior patterns, peer conflict, social harm, and parent communication.
Develop and monitor student accountability plans (behavior growth plans, restorative agreements, reentry supports) with clear expectations, timelines, and follow-up.
Schoolwide Attendance Ownership, Monitoring, and Intervention
Own attendance as a primary schoolwide operational and culture priority, ensuring that systems are accurate, timely, and action-oriented.
Establish consistent procedures across divisions for daily attendance capture, late arrivals, early dismissals, and documentation of absences.
Monitor attendance and punctuality trends and conduct regular reviews (daily for urgent concerns; weekly for patterns; monthly for strategic analysis).
Lead a structured attendance intervention system that includes early outreach, barrier identification, family partnership, and escalating supports when patterns persist.
Convene and lead attendance-focused meetings (as needed) with division directors, counselors, learning support, and families to remove barriers and restore consistent attendance.
Ensure consistent enforcement of handbook attendance expectations, including consequences and/or privilege eligibility rules where applicable (e.g., athletics, events, leadership roles), in alignment with school policy.
Family Handbook Governance and Consistent Enforcement
Serve as a primary steward of the Family Handbook’s student-life sections (attendance, conduct, community expectations, discipline processes), including annual review, revision recommendations, and community communication.
Translate policy into daily practice by creating clear internal procedures, decision trees, templates, and communication norms.
Ensure that faculty understand expectations, referral processes, and documentation requirements, and that families experience communication that is timely, respectful, consistent, and solutions-oriented.
Student Support Team Coordination and Wrap-Around Partnership
Serve as a core member (and often chair) of student support meetings related to conduct, attendance, and school culture, ensuring that academic, social-emotional, and behavioral supports are integrated.
Partner closely with counseling/wellness staff so that accountability is paired with appropriate support and risk-responsive care.
Coordinate cross-division transitions and reentry supports for students returning from extended absences, leaves, or significant disciplinary events.
Communication, Change Management, and Adult Leadership
Communicate clearly and consistently with students and families—especially in moments where expectations are not being met—while maintaining a calm, restorative, and firm stance.
Coach adults across divisions toward consistent practice, including classroom management support where needed and coaching on restorative responses.
Build trust and buy-in through transparency, prompt follow-through, and predictable processes.
Serve as a visible, values-driven presence during key times (arrival, lunch, passing periods, dismissal) and at major events, modeling steady leadership.
Data Systems, Documentation, and Operational Excellence
Maintain accurate, confidential records related to attendance, behavioral incidents, restorative interventions, and outcomes, in alignment with school policy and applicable requirements.
Build usable dashboards and reporting rhythms for leadership (attendance patterns, referral patterns, response timelines, intervention outcomes).
Ensure strong operational coordination with administrative offices, advisors, and student information systems so that accountability work is not undermined by inconsistent data or inconsistent procedures.
Professional Responsibilities and School Life
Participate in relevant leadership meetings and provide regular updates to the Head of School regarding school culture, attendance trends, and implementation progress.
Engage in ongoing professional learning in restorative practices, student development, and attendance intervention best practices.
Uphold the highest standards of professionalism, judgment, confidentiality, and ethical practice.
Perform other duties as assigned in service of student wellbeing, school culture, and institutional effectiveness.
Required Qualifications
The School seeks a true expert. Candidates should bring a record of distinguished practice and demonstrated success building sustainable systems across multiple grade levels.
Master’s degree required (or higher strongly preferred) in Educational Leadership, Counseling, School Psychology, Social Work, Student Development, or a closely related field.
Minimum of 8 years of successful experience in student life leadership and/or dean/assistant head/divisional leadership roles, with significant direct responsibility for student conduct systems and family-facing accountability.
Demonstrated expertise implementing restorative practices at the systems level, including facilitation skill (circles/conferences/mediation), staff training/coaching capacity, and evidence of durable implementation (not just pilot exposure).
Demonstrated success leading attendance systems and interventions, including accurate monitoring, early outreach protocols, documentation, family conferencing, and measurable improvement outcomes.
Strong fluency with child and adolescent development, including the social dynamics and developmental needs of middle and high school students.
Proven ability to coach and lead adults—strengthening consistency of practice across faculty and helping teams hold firm boundaries with warmth and clarity.
Demonstrated ability to apply handbooks/policies consistently and fairly, including strong investigative judgment, documentation habits, and decision-making discipline.
Exceptional communication skills: calm, precise, respectful, and timely written and verbal communication with students, parents/guardians, and colleagues.
Demonstrated commitment to equity and belonging, including the ability to reduce bias in discipline processes and ensure consistent dignity-centered practice.
Strong operational competence with student information systems, documentation workflows, multi-stakeholder coordination, and high-volume follow-through.
Ability to maintain a highly visible campus presence and a schedule that includes some evenings/weekends for student life events as needed.
Preferred Qualifications
Doctorate (EdD/PhD) or advanced specialist degree in a relevant discipline.
Formal restorative practices credentialing or extended training pathway (e.g., multi-day institutes plus coaching/implementation experience), with evidence of having trained other adults.
Experience in an independent school environment with high expectations for family partnership, student conduct consistency, and mission-driven culture.
Experience designing multi-tiered student support structures (MTSS/RTI-B style) that integrate behavior, attendance, and wellbeing supports.
Training in threat assessment/safety protocols, crisis de-escalation, or related student safety frameworks appropriate for school settings.
Personal Attributes and Professional Dispositions
The successful candidate will be warm, steady, and credible; able to hold firm expectations with care; and skilled at building trust while also driving accountability. This leader will bring the courage and discipline to address serious attendance problems directly, the relational intelligence to partner with families productively, and the systems mindset to make consistent follow-through the norm across divisions.
How to Apply:
Qualified candidates are invited to submit a single PDF document including the following materials:
Cover letter (letter of interest)
Current résumé/CV
Brief statement of educational philosophy
Names and contact information for three professional references
Please email your application materials to Autumn at ademott@canterburyschool.org, with the subject line: [Position Title] Application – [Last Name].
The mission of Canterbury School is to maximize the potential of young people by providing a challenging, enriching, and supportive learning environment in which students build the foundation for a life of purpose, passion, and meaning.