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Service Learning Advisor Westover School - 4.0 Middlebury, CT Job Details Temporary | Part-time $2,500 - $4,000 a month 14 hours ago Qualifications School experience Experience working with 12th graders Faculty collaboration Bachelor's degree Experience working with middle schoolers Working with students Student activities (student support initiatives) Stakeholder relationship building Full Job Description Middlebury, CT $2,500 ‒ $4,000

Annually Department:

Athletics Location:

Westover School -

Middlebury, CT Status:

Temporary;

Part-Time About Us:

Westover School is an all-girls' boarding and day school for grades 9-12, where smart, motivated students become confident, connected women. We are committed to providing a college preparatory education in a small community atmosphere that emphasizes meaningful student-adult relationships. We EMPOWER students to be themselves, make their own choices, and appreciate diversity—resulting in graduates who lead lives of purpose and meaning, understand they can make a difference, and value the power of relationships. We invite you to apply for the role of Service Learning Advisor for the 2026-2027 winter season, beginning in late November and running through the beginning of March. Why Westover? 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, 1.5 hours from New York City, and 2 hours from Boston.

Job Summary:

The Service Learning Advisor will coordinate and facilitate meaningful community-based learning experiences for students as part of Westover's winter afternoon activities program. This individual will work collaboratively with students, faculty, and local community organizations to develop opportunities that connect service, reflection, leadership, and personal growth. The ideal candidate is a student-centered individual who is organized, collaborative, and passionate about helping young people engage meaningfully with their communities. The program meets Monday through Friday between 4:00 and 6:00 p.m., with Wednesday activities potentially beginning as early as 2:30 p.m.

Responsibilities and Duties:

Coordinate and supervise student service-learning experiences with local community partners. Develop and maintain positive relationships with schools, nonprofit organizations, and community groups. Guide students through preparation, participation, and reflection connected to their service experiences. Manage program logistics, including schedules, transportation, attendance, permissions, and communication. Foster a safe, inclusive, and supportive environment for student participation. Support students in developing empathy, leadership, responsibility, and civic engagement. Collaborate with faculty and school leadership to ensure programming aligns with Westover's educational mission.

Required Skills and Qualifications:

Valid Connecticut A-Endorsement License or willingness to obtain one within a designated timeframe following hire. Bachelor's degree required; master's degree preferred. Experience working with middle or high school students. Experience with service learning, community engagement, experiential education, or a related field preferred. Strong organizational, communication, and relationship-building skills. Ability to coordinate activities, manage logistics, and work collaboratively with students and colleagues. Enthusiasm for working with adolescents and connecting students to meaningful community experiences.

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.