Founded in 1886, The Winsor School is a nationally recognized independent day school for girls in grades 5–12, located in the heart of Boston’s Longwood academic and medical community. Winsor has long been committed to educating intellectually curious, motivated students in an environment that values both tradition and innovation. The School’s mission is to empower young women to pursue their passions, think critically, and lead with integrity and purpose.
Working at Winsor means joining a vibrant, collaborative community of educators and professionals dedicated to academic excellence and student well-being. The School is deeply invested in equity and belonging, weaving diversity and inclusion into its strategic priorities and daily life. With small class sizes, meaningful mentoring, and a dynamic co-curricular program, Winsor provides a holistic educational experience. Its location in Boston offers access to world-class universities, cultural institutions, and medical centers, further enriching both student and professional life.
The Opportunity
The Winsor School seeks an accomplished, relationship-driven Director of Major Gifts to help secure transformational philanthropic support during a historic moment in the School’s trajectory.
Reporting to the Chief Advancement Officer, the Director will manage a robust portfolio of donors and prospects, primarily at the six- and seven-figure levels, while also cultivating new philanthropic relationships. This senior position will be central to Winsor’s advancement strategy, as the School nears the close of Winsor Leads, a $100 million campaign that has already galvanized record community participation and delivered far-reaching impact for students and faculty.
The Director will serve as a frontline fundraiser and a mentor within the Advancement team, helping to foster a culture of collaboration, transparency, and shared purpose. With Winsor’s philanthropic community highly engaged and deeply invested in the mission, the successful candidate will bring both the discipline of metrics-driven fundraising and the intuition to cultivate authentic, enduring relationships. This role requires confidence, intellectual credibility, and warmth, as well as the ability to navigate complex donor relationships with trustees, alumnae, and senior volunteers.
For an experienced advancement professional, this is an opportunity to join a mission-driven school with extraordinary momentum, work closely with inspiring institutional leadership, and help secure the philanthropic resources that will shape Winsor’s future. The position offers not only the chance to strengthen Winsor’s culture of giving but also the opportunity to play a key role in advancing the mission of preparing young women to lead lives of purpose.
