Westover School (Westover), an independent, college-preparatory boarding and day school for girls in Middlebury, Connecticut, seeks a dynamic fundraiser and team leader with a proven track record to serve as its next Director of Advancement (DOA).
Reporting to the Head of School, the Director of Advancement will oversee all aspects of Westover’s fundraising, alumnae and parent engagement programs, and further strengthen a growing culture of
philanthropy. With a deep belief in Westover’s mission and the transformative power of girls’ education, the Director of Advancement will help shape the strategic direction of the advancement office and
position the School for its next phase of growth.
This work will be accomplished through a comprehensive, goal-driven advancement strategy and the cultivation of enduring relationships across the Westover community.
About Westover School
Westover School is a girls-centered boarding and day school for grades 9-12. At Westover, students are seen for who they are and celebrated for their intellect, curiosity, and unique passions. This is a community where innovative academics foster intellectual empowerment, collaboration thrives, and faculty inspire bold exploration. Rooted in sisterhood, friendships here are lifelong
and unbreakable.
Since 1909, Westover has provided a transformational college preparatory education through small classes (average size 12), rigorous academics with 21 AP and Honors courses, and a close-knit community. Today, 200 students from 20 states and 24 countries attend Westover; 67 percent identify as students of color and 68 percent are boarding students.
Mission and Values
Westover School embodies a simple yet bold vision: Westover School empowers young women to lead lives of consequence.
Core Values: Strength of Character, Women’s Empowerment, Passion for Learning and Community
Leadership
In partnership with Head of School Polly Fredlund, Westover is governed by an 18-member Board of Trustees and is supported by an 18-person Alumnae Board of Governors.
The Board of Trustees provides governance, fiduciary oversight, and strategic leadership through a committee structure.
The Board of Governors serves as ambassadors, strengthening engagement among alumnae, parents, and friends.
Student leadership is central to campus life, with elected students serving on key committees.
Position Details
Advancement at Westover
Philanthropy sustains Westover beyond tuition, expanding opportunities for students and faculty while advancing the School's mission. The Office of Advancement strengthens connections among alumnae, parents, friends, and the broader Westover community. The most recent comprehensive campaign at Westover, the Inspiring Women Campaign, yielded $51.5M for the school, providing exceptional stability for operations and aid in building the endowment. Today, Westover benefits from 100 percent board participation, 100 percent faculty and staff participation, and a steady annual fund, which yields over $2.3M each year.
Director of Advancement
Reporting to and partnering closely with the Head of School, the Director of Advancement will serve as the strategic and tactical leader for all philanthropy and donor relations activities at Westover. The Advancement Office includes five professionals supporting advancement services, events, annual giving, constituent relations, and operations.The DOA will have the opportunity to hire additional staff, serve as staff liaison to the Advancement Committee and related Board subcommittees, partner with parent and alumni volunteers, and serve as a key member of the Head of School's Senior Team.
Furthermore, the DOA will prioritize the following opportunities:
Maintain and enhance a philanthropic culture: Building on a strong foundation of engagement and dedicated volunteers, the DOA will deepen Westover's culture of philanthropy, strengthening the School's long-term financial health.
Expand and diversify prospect and donor engagement: While sustaining strong engagement from faculty, staff, trustees, alumnae, and parents, the DOA will broaden and diversify the donor pipeline by engaging historically under-engaged constituencies and expanding planned giving and international engagement.
Prepare and execute a comprehensive campaign: The DOA will lead planning and execution of Westover's next comprehensive campaign, partnering closely with the Head of School to develop campaign strategy, articulate a compelling case for support, and maximize fundraising impact.
Support, mentor, and develop a talented team: The DOA will align responsibilities with individual strengths, establish clear goals, and empower staff to succeed.
Deepen cross-campus collaboration: The DOA will strengthen communication and partnership across campus while working closely with the Head of School to support successful donor engagement.
Strengthen advancement infrastructure and data practices: The DOA will ensure systems, technology, and data practices support accurate reporting, operational efficiency, and strategic decision-making.
Candidate Profile
The ideal candidate will be deeply committed to Westover's mission of empowering young women to lead lives of consequence. While primarily externally facing, the next DOA will value being connected to daily campus life, supporting students while sharing their stories with the broader community.
Candidates should hold a bachelor's degree; a master's degree is preferred. The ideal candidate will demonstrate many of the following qualities and skills:
- Extensive front-line fundraising experience at a leadership level.
- Success developing, leading, and empowering high-performing teams.
- Confidence leading ambitious fundraising campaigns.
- Ability to partner closely with the Head of School to maximize donor and prospect engagement.
- Inspirational storytelling and exceptional relationship-building skills.
- Commitment to being an engaged member of the campus community.
- Strategic, innovative approach to long-term planning.
- Experience leading or playing a significant role in a comprehensive campaign, including establishing metrics, evaluating performance, and seeing the campaign through completion.
- Strong understanding of advancement systems, CRM platforms (including Raiser's Edge), data management, and best practices for data integrity.
- Unimpeachable integrity, sound judgment, and a commitment to confidentiality.
- Exceptional interpersonal and communication skills.
- Trustworthy, self-motivated, and proactive.
Compensation and Benefits
This is a full-time, on-site position in Connecticut. Salary is commensurate with experience. The salary range for this role is $200,000 to $215,000 with a generous benefits package, including housing and potential tuition remission. To learn more about Westover’s offerings, please see their employment page.
DSG | Storbeck has been exclusively retained for this engagement, led by Matthew Marsallo and Anne Koellhoffer. Express interest in this role by filling out our Talent Profile or emailing the search team directly
at [email protected]. All inquiries are confidential.
Equal Employment Opportunity
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.
**This leadership profile is not exhaustive and may be subject to change. While every effort has been made to confirm information at the date of publication, the accuracy or completeness of the information provided herein cannot be guaranteed.
