Director of Advancement

Director of Advancement | Westover School
Middlebury, CT
April 2026

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.

In addition to the DOA, the Advancement Office at Westover currently includes a staff of five: Advancement Services Manager, Advancement Projects and Events Manager, Director of the Westover Fund, Families Liaison, and Marketing Coordinator. The DOA will have the opportunity to hire additional staff once on board. The DOA will also serve as the staff liaison to the advancement committee and related subcommittees of the board of trustees and work closely with parent and alumni volunteers, in addition to serving as a key member of the Head of School’s Senior Team.

The ideal candidate will have a strong desire to work towards Westover’s mission of empowering young women to lead lives of consequence. While primarily an externally facing role, the next DOA will understand the essentialness of having connections with the daily life of the school, and will seek to embed themselves to both aid in supporting Westover’s students and then share their stories with the broader community. Candidates should hold a bachelor’s degree, with a master’s degree preferred.

This is a full-time position that will be performed on site in Connecticut. Salary is competitive and 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 View email address on click.appcast.io. All inquiries and discussions are strictly confidential.