Teaching FellowLocation: Middlebury, CT 

Primary Reporting: Director of Community Life, Director of Teaching and Learning

Reporting: Associate Head of SchoolStatus: 

Full-time, one-year fellowship, 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.

Westover is dedicated to empowering young women through rigorous academics, student-centered learning, and a supportive residential experience. Fellows play an important role in fostering academic curiosity, building community connections, and supporting our mission to educate and inspire future leaders.

Job Summary

Westover School seeks recent college graduates with a passion for teaching and learning to join our community as a Teaching Fellow. This one-year fellowship provides immersive experience in a boarding school environment, offering hands-on opportunities to teach, mentor, and engage with students while gaining insight into independent school education.

Fellows support teaching and learning across disciplines by assisting with instruction, collaborating with faculty, and engaging directly with students in academic settings. They contribute to academic programming and participate fully in campus life. This role is ideal for early-career educators or individuals exploring a future in education and includes structured mentorship, professional development, and broad exposure to classroom instruction and residential life.

Responsibilities and Duties

Teaching and Academic Support

• Co-teach and/or assist in academic courses, contributing to lesson planning, classroom instruction, and student assessment.
• Provide academic support through one-on-one tutoring, small group instruction, and student mentoring.
• Engage in curriculum development projects and assist in creating dynamic and inclusive learning experiences.
• Contribute to special academic initiatives, including project-based learning, research projects, or experiential education opportunities.

Residential Life and Student Engagement

• Serve as dorm faculty and participate in the residential duty rotation during weekdays and weekends.
• Build positive relationships with students, providing guidance and support in the dormitory setting.
• Support student activities, including clubs, affinity groups, and school traditions.
• Promote an inclusive community culture and demonstrate respect for diversity, equity, and inclusion.

After-School Programs

• Participate in three seasons of after-school activities, which may include coaching athletics, leading arts programs, or facilitating clubs and extracurricular programs.
• Bring energy and creativity to afternoon programming, engaging students in meaningful experiences beyond the classroom.

Additional Expectations

• Attend all required school functions, including meetings, events, and community gatherings.
• Fulfill general faculty expectations, including professional responsibilities, committee participation, and community engagement.
• Take on additional duties as assigned in support of school operations and student life.

Required Qualifications and Skills

• Bachelor’s degree required.
• Strong interest in pursuing a career in education or working with adolescents.
• Ability to connect with students and build positive relationships in both academic and residential settings.
• Enthusiasm for boarding school life, including teaching, residential responsibilities, and student activities.
• Cultural competency and commitment to diversity, equity, and inclusion.

Working Conditions

This is a residential fellowship requiring evening, weekend, and overnight responsibilities as part of the dorm duty rotation. Fellows are expected to participate fully in academic, residential, and co-curricular programs and to maintain an active presence on campus. Work is performed in classrooms, residence halls, athletic facilities, and other campus spaces.

Physical Requirements

• Ability to move throughout campus, including residence halls, academic buildings, and athletic facilities.
• Ability to stand for extended periods during classes, activities, and events.
• Ability to lift or move up to approximately 25 pounds.
• Ability to communicate effectively in person, by phone, and electronically.

Compensation and Benefits

This is a full-time, one-year residential fellowship, with room and board provided during the academic year. Westover School offers a comprehensive benefits package for eligible employees, including:

• Health and vision insurance
• Dental reimbursement
• Health Reimbursement Arrangement (HRA)
• Life insurance
• Retirement plan
• Professional development support
• On-campus housing is provided in accordance with school residential policies.

Equal Employment Opportunity (EEO) Statement

Westover School is an Equal Opportunity Employer and does not discriminate based on race, color, religion, national origin, ancestry, citizenship status, age, disability, sex, marital status, veteran status, sexual orientation, gender identity or expression, genetic information, or any other characteristic protected by applicable law. We are committed to building a diverse and inclusive community and strongly encourage applications from candidates from historically marginalized or underrepresented backgrounds, as well as those with non-traditional career paths.