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Assistant Director of Community Life

Job in Middlebury, New Haven County, Connecticut, 06762, USA
Listing for: Westover School, Incorporated
Full Time position
Listed on 2026-03-11
Job specializations:
  • Education / Teaching
    Education Administration
Salary/Wage Range or Industry Benchmark: 80000 - 100000 USD Yearly USD 80000.00 100000.00 YEAR
Job Description & How to Apply Below

Assistant Director of Community Life
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…
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