Job Title: Assistant Director of Advancement - Constituent Relations

Department: Advancement 

Reports to: Chief Development Officer

Location: Middlebury, Connecticut 

Position Type: Full-Time 12 months

About Us: 

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.

Job Summary: 

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.

Responsibilities and Duties:

• 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.
• Recruit, train, and support volunteers, empowering them to enhance engagement, increase attendance, and advance fundraising goals.
• 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.

Required Qualifications and Skills:

• 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 GiveCampus), and a comfort level with social and professional networking platforms (e.g., LinkedIn, 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.

Working Conditions:

• 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 typically Monday through Friday, occasional evenings and weekends may be required to support events, donor activities, or critical project deadlines. Willingness to travel and participate in evening or weekend events as needed to support engagement goals.The school fosters a collegial workplace where mutual respect, attention to detail, and service-oriented collaboration are paramount. As part of the Advancement team, the Director may attend offsite meetings, workshops, or professional development conferences that align with institutional priorities.

Physical Requirements:

• Ability to remain in a stationary position, operate a computer, and communicate effectively for extended periods.
• Occasionally move event materials or equipment weighing up to 25 pounds.
• Ability to travel by car, train, or plane as needed.
• Navigate campus buildings and outdoor spaces, including stairs and uneven terrain.

Compensation and Benefits:

• Competitive salary commensurate with experience.
• Comprehensive benefits package including:
  • Health and vision insurance
  • Dental reimbursement
  • Health reimbursement arrangement
  • Life insurance
  • Retirement plan with employer contributions
• Professional development support

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.