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Teaching Fellow
Westover School
Application
Details
Posted: 14-May-26
Location: Middlebury, Connecticut
Type: Full Time
Categories:
Other
Additional Information:
2 openings available.
Teaching Fellow Location: Middlebury, CT Primary Reporting: Director of Community Life, Director of Athletics, Department Heads Secondary Reporting: Associate Head of School Status: 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
The physical demands described here are representative of those that must be met to successfully perform the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform essential functions.
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 with employer contributions
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.
Westover School is an all-girls' boarding and day school, grades 9-12 where smart, motivated girls become confident, connected women. We are committed to providing a college preparatory education in a small community atmosphere that emphasizes student-adult interaction. Westover, through program and faculty, endeavors to develop in each student the confidence and strength to shape her own life - to become the best that she can be.
We celebrate diversity of all kinds and are committed to creating an inclusive culture built on a foundation of respect for all individuals. We seek to hire, develop and retain talented people from all backgrounds. Individuals from non-traditional backgrounds, historically marginalized or underrepresented groups are strongly encouraged to apply.
Westover School is located in Middlebury, CT; 45 minutes from New Haven, 1 1/2 hours from New York City, and 2 hours from Boston. For more information, please visit our website at www.westoverschool.org.
Westover School is an Equal Opportunity Employer.
Application Notes:
Interested candidates should address these aforementioned qualifications and skills in their cover letter in addition to providing a résumé. Please see the employment page at westoverschool.org.