Assistant Director of - Constituent Relations

Job Title: Assistant Director of Advancement - Constituent Relations

Department: Advancement

Reports to: Chief Development Officer

Location: Middlebury, Connecticut

Position Type: Full-Time 12 months

Westover School is an all-girls boarding and day school in Middlebury, Connecticut, with a mission to empower young women to lead lives of consequence. We are committed to fostering a diverse, inclusive, and globally minded community where students thrive academically and personally.

The Advancement Office’s mission is to engage constituents in the life of Westover School through engagement and philanthropy. The Assistant Director of Advancement plays a critical role by providing both strategic leadership and daily management of engagement initiatives within the Office of Advancement. This role fosters meaningful connections between Westover and its alumnae, families, and friends, oversees key volunteer programs, and develops initiatives that enhance constituent involvement.

• Serve as Alumnae Director and Families Liaison, acting as the primary point of contact for all inquiries, opportunities, and relationship-building efforts.
• Lead a comprehensive Governors and Families Association program that strengthens the Office of Advancement’s reach and impact through engaged leadership and meaningful service.
• Oversee the vision, planning, and execution of Westover’s annual Reunion, creating memorable experiences that deepen connections among alumnae and the School.
• Design and implement regional, virtual, and on-campus events that inspire participation and strengthen constituent engagement with Westover.
• Develop and deliver innovative engagement initiatives that align with staffing capacity, program priorities, and philanthropic objectives.
• Identify and promote opportunities to celebrate constituent contributions, integrating their stories and achievements into the life of the School.

• Bachelor’s degree required; advanced degree in communications, nonprofit management, education, or a related field is strongly preferred.
• 2+ years of progressive experience in alumnae/i relations, advancement, volunteer management, or constituent engagement, ideally within an educational or mission-driven nonprofit setting.
• Demonstrated success in building and managing volunteer programs, advisory boards, or alumni governing bodies with measurable outcomes.
• Experience in strategically designing and executing events (in-person, regional, and virtual) that inspire connection and deepen organizational loyalty.
• Excellent written and verbal communication skills with the ability to craft compelling messages and engage varied constituencies with authenticity and purpose.
• Strong interpersonal and relationship-building skills; a natural connector and listener with high emotional intelligence and a sincere enthusiasm for people.
• Proven ability to work both independently and collaboratively in a high-performing, mission-focused environment where integrity, discretion, and follow-through are essential.
• Proficiency with CRM platforms (Raiser’s Edge/NXT preferred), event and communication tools (such as YAMM, Zoom, and Give Campus), and a comfort level with social and professional networking platforms (e.g., Linked In, Alma Connect, Instagram).
• Commitment to equity, inclusion, and culturally responsive engagement with constituents from a wide range of backgrounds.
• Familiarity with the traditions, rhythms, and values of a boarding and day school community, especially one that cultivates leadership and empowerment in young women, is highly desirable.

• This position is primarily office-based and located on the campus of Westover School in Middlebury, Connecticut with some regional travel within the United States. The role requires a high degree of interaction with faculty staff and constituents, both in person and through digital platforms. The Assistant Director of Advancement - Constituent Relations will work in a collaborative and mission-driven environment that values professionalism, discretion, and a deep commitment to Westover’s advancement goals.
• While standard hours are…