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Assistant Director of Community Life

Job in Middlebury, New Haven County, Connecticut, 06762, USA
Listing for: Westover School
Full Time position
Listed on 2026-03-12
Job specializations:
  • Education / Teaching
    Education Administration, Youth Development
Salary/Wage Range or Industry Benchmark: 80000 - 100000 USD Yearly USD 80000.00 100000.00 YEAR
Job Description & How to Apply Below

Department: Student Life

Reports to: Director of Community Life & Culture

Status: Full-time, 10-month, residential position

About Us

Westover School is a gender‑inclusive girls boarding and day school for grades 9–12. Our community is built on close student–adult relationships, shared responsibility, and a deep belief that young people thrive when expectations are clear, care is consistent, and belonging is intentional.

The Office of Community Life plays a central role in shaping the lived experience of students s work requires presence, sound judgment, compassion, and the ability to translate values into daily practice within a residential school environment.

Job Summary

The Assistant Director of Community Life is a senior member of the Student Life leadership team and is responsible for the day‑to‑day coordination, consistency, and execution of residential and community life programming. This role provides critical leadership in residential life operations, student accountability, and community standards, ensuring students experience a predictable, supportive, and equitable environment.

Working in close partnership with the Director of Community Life & Culture, the Assistant Director supports students through daily challenges, reinforces community expectations, and helps maintain a healthy and well‑functioning residential program. This position requires regular evening, weekend, and on‑call responsibilities, as well as a visible and relational presence with students.

Responsibilities and Duties Residential Life Leadership
  • Provide primary oversight of the residential life program, supporting approximately 175 boarding students.
  • Supervise and support dorm parents and residential faculty in collaboration with the Director of Community Life & Culture.
  • Coordinate residential duty schedules, evening and weekend coverage, and on‑call systems.
  • Lead the development and implementation of residential programming, including health, wellness, and life skills initiatives.
  • Serve as a first responder for residential concerns, student needs, and emergent situations during assigned coverage.
Community Standards and Accountability
  • Oversee minor disciplinary processes, including dress code, phone policy, and general community expectations.
  • Ensure consistent enforcement of community standards across grade levels and residential spaces.
  • Facilitate restorative conversations and accountability processes at the minor to moderate level.
  • Track patterns and trends in student behavior and communicate concerns and recommendations to the Director of Community Life & Culture.
  • Partner with and support the Community Life Coordinator as a primary interventionist for minor accountability and student support needs.
Student Leadership and Traditions
  • Partner with and support the Traditions and Activities Coordinator in the planning and execution of traditions and community programming.
  • Support student leadership structures, elections, and leadership development initiatives.
  • Collaborate with community life colleagues on the planning and execution of signature school events.
  • Maintain a visible presence at community events, residential programs, and student activities.
Program Operations and Collaboration
  • Play a key role in Welcome Week planning and execution, particularly related to residential readiness and student onboarding.
  • Partner with academic, counseling, health, and international student support teams to provide coordinated student care.
  • Assist with school opening and closing logistics related to residential life and student transitions.
  • Participate actively in the dorm duty rotation, including evening and overnight responsibilities.
Required Qualifications And Skills
  • Demonstrated commitment to student‑centered education and adolescent development.
  • Experience working in residential life, boarding schools, or comparable student life environments.
  • Ability to establish clear expectations while maintaining warmth, empathy, and trust with students.
  • Strong judgment and capacity to respond calmly and effectively in crisis situations.
  • Commitment to diversity, equity, inclusion, and culturally responsive practices.
  • Excellent communication, organizational, and…
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