The Winsor School | Boston, Massachusetts
Since its founding in 1886, the Winsor School has been a defining presence in Bostons independentschool community, known for its rigorous academic program for girls in grades 512, its urban location, and its deep commitment to preparing young women for lives of purpose, service, and leadership. Drawing from its legacy and missionto prepare young women to pursue their aspirations and contribute to the worldWinsor continues to evolve thoughtfully while remaining true to its core values of intellectual curiosity, personal integrity, and authentic engagement.
As Winsor embarks on its next chapter of growth, the school seeks a strategic and missionaligned leader to serve as its next chief advancement officer (CAO). This is a compelling opportunity for an experienced advancement professional to shape and elevate the philanthropic efforts of one of the nations premier independent schools for girls. The CAO will lead a comprehensive, integrated advancement programencompassing annual giving, major and planned gifts, alumnae and parent engagement, donor stewardship, volunteer leadership, campaign planning and execution, and advancement operations. The successful candidate will partner closely with the head of school, board of trustees, senior leadership, faculty, alumnae, parents, and key external stakeholders to expand philanthropic support in alignment with Winsors strategic vision.
Importantly, Winsor is currently in the final phase of its Winsor Leads Campaign, a $100million comprehensive campaign that has raised more than $75 million to date. With alumnae participation exceeding 50 percent and gifts coming in from 46 states and the District of Columbia, this campaign presents an extraordinary moment to join and accelerate the schools philanthropic momentum. The ideal candidate will bring a distinguished track record in fundraising and advancement leadershipespecially within independent schools or missiondriven nonprofits, a collaborative mindset, and the ability to tell a compelling story about Winsors mission and impact. As a member of the senior leadership team, the CAO will be instrumental in securing support for Winsors next phase of institutional strength and programmatic excellence.
Founded in 1886 by Mary Pickard Winsor, who began a sixmonth school for eight girls in Bostons Back Bay, Winsor has grown from its modest origins into a distinguished collegepreparatory institution for girls in grades 5 through 12. Miss Winsors founding purpose was to prepare young women to be selfsupporting, competent, responsible, and generousmindedan ethos that continues to shape Winsors identity and program. The school relocated in 1910 to its current location in the Longwood neighborhood, placing it at the nexus of Bostons academic, medical, and cultural life. Throughout its history, Winsor has sustained a commitment to excellence in girls education, fostering intellectual depth, personal character, and global responsibility. Its facilities, curriculum, and community have evolved to meet the needs of a changing world while preserving a strong sense of purpose. Today, Winsor stands as an outstanding example of how a historic institution can continue to innovate, adapt, and lead, preparing young women to make meaningful contributions in a complex, interconnected world.
At Winsor, the program is the lived expression of its mission: to turn curious, motivated learners into strong, purposeful women. Since its founding, Winsor has brought together rigorous intellectual work, inspired creative expression, competitive athletic engagement, and rich extra and cocurricular opportunities. Winsor is known for its intellectually serious environment, where students who love to ask thoughtful questions, dig into complex ideas, and tackle challenging problems feel at home. The schools citycentral location provides unique opportunities for students to learn, play, and volunteer in and around Boston, building connections with others far beyond campus. Learn more about the opportunities for engaging with the community here.
The curriculum spans Lower School (grades 58) and Upper School (grades 912) and is designed to nurture confidence, independence of mind, and readiness for college and beyond. Core academic values include depth of study, meaningful connections between faculty and students, support for the whole person, and exploration beyond the classroom. Students are encouraged not only to absorb knowledge, but to become bold doersapplying, creating, and leading. One senior faculty leader, in describing the unique opportunity an allgirls school offers said, In our classrooms, we dont say, I might be wrong, but Girls here learn not to explain away their intellect. Learn more about Winsors academic program and curriculum here.
Creating an environment of respect and inclusion is a matter of principle at Winsor. From a student equity board comprised of four committees in the Upper School, to more than a dozen affinity groups designed to create space for underrepresented groups to experience being in the majority, to opportunities for faculty and staff to explore questions around identity and topics of social and cultural importance, the school works diligently to create a sense of belonging for every member of the Winsor community.
At Winsor, athletics are not an afterthought; they offer students a daily context for discipline, teamwork, resilience, and leadership. Students in grades 612 have access to 14 teams plus interscholastic options in rowing and sailing or club sports in golf and curling, and the school belongs to the Eastern Independent League (EIL) and the New England Prep School Athletic Conference (NEPSAC). These opportunities, along with physical education, allow all students to participate in physically challenging pursuits each day. The athletic program is designed not only for competition, but for lasting experiences that foster important character development, win or lose.
Winsors arts program ensures that creativity, selfexpression, and collaboration stand alongside intellectual and athletic rigor. Students engage in a wide array of visual arts, music, theater, and dance; even in the Lower School the arts are woven into the schedule, and in the Upper School there are advanced electives and immersive experiences. From designing sets to acting, and composing to directing, students develop confidence in voice and presence, skills that translate beyond the stage into every domain of life.
Winsor doesnt stop with the typical offeringsit builds signature experiences that align with its urban Boston location, allgirls mission, and commitment to depth and discovery. The campus brings together students across grades 512 which enables mentorship, continuity, and vertical leadership opportunities. Additionally, seniors engage in an Independent Learning Experience (ILE) that allows them to study an area of interest independently. Each student designs her own project, guided by a faculty seminar leader and an expert mentor in her area of interest. Winsor students engage in the ILE during the final four weeks of senior year. The project culminates in a celebration where students present their projects to the whole Winsor community.
Global studies that push beyond the classroom into research and realworld contexts also abound. In the Upper School, students have the opportunity to participate in School Year Abroad, The Mountain School, or the School for Ethics and Global Leadership.
Head of School: Meredith Legg brings a uniquely powerful blend of engineering mindset, educational innovation, and girlsschool leadership to her role as head of school. Before she joined Winsor, she served as associate head of Emma Willard School, a day and boarding school for young women, where she oversaw academic programs, professional development, faculty hiring and performance management, curriculum innovation, learning support, academic and strategic technology, and experiential learning. Prior to that, her earlier tenure at Emma Willard included roles as academic dean, chair/director of academic technology, interim STEAMteam lead, and even as a teacher of physics, engineering, and environmental science. Meredith holds a B.S.]]> <
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