Head of the Upper School

Founded in 1886, The Winsor School is an independent girls’ school for academically promising and motivated students in grades five through twelve. Located in the heart of Boston’s Longwood Medical and Academic Research area, our students benefit from the school's longstanding commitment to providing a superior education for girls, inspirational and dedicated faculty, and diverse and talented community. Winsor strives to consciously create an environment of respect and inclusion and to support ethnic, racial, religious and socio-economic diversity among all the constituencies of the school. Winsor supports this commitment through its inclusive curriculum, success addressing a range of learning styles, availability of a wide array of diversity efforts and programs, and participating in the greater Boston community.

Head to Upper School
For more than 140 years, The Winsor School has empowered generations of girls to pursue their aspirations, discover new talents, hone critical skills, and contribute to the world. Serving students in grades 5 through 12, Winsor is unwavering in its commitment to developing students of conviction with strong voices and expansive intellectual capacity. That same intellectual depth and passion for learning define a faculty whose members, with an average tenure over 20 years, bring extraordinary expertise, commitment, and enthusiasm to their teaching. Located in the Longwood neighborhood of Boston near Fenway Park, Winsor attracts and nurtures students who are authentic, joyful, energetically curious, and academically confident. Says one faculty member, “Winsor students let you take them on intellectual adventures.” While academic excellence is at its core, the classroom experience is just the beginning. Students are not only thinkers and scholars but also athletes, artists, community volunteers, club members, leaders, mentors, and
friends.
In 1886, Mary Pickard Winsor opened a six-month school for eight girls at 334 Boylston Street in Boston’s Back Bay, the first of six locations in various townhouses in the neighborhood. Ahead of her time, Miss Winsor wanted to prepare women to be self-supporting and hoped they would be competent, responsible, and generous-minded. By 1900 the student body had grown to 99 girls; in 1910 the school relocated to its current location in the Longwood area. Now serving 474 students on a single campus, Winsor’s state-of-the-art facilities, including the Lubin-O’Donnell Center for the performing arts, athletics, and wellness, which opened in 2015, reflect and enhance the excellent education each student receives.

The head of Upper School is a central presence in the life of Winsor, providing thoughtful, student-centered leadership to a dynamic community of adolescents, faculty, and families. In a school known for the strength of its relationships, intellectual ambition, and deep commitment to its students, the head of Upper School helps create the conditions for students and faculty to do their best work and for the Upper School to flourish as an essential part of the larger 5–12 community. Working closely with the head of school and senior leadership team, the head of Upper School will help shape Winsor’s future while honoring the traditions, values, and distinctive qualities that make the school special. This is a role that calls for vision and follow-through, warmth and accountability, and the ability to attend to both the big picture and the details of daily school life. A close partner to the head of Lower School (grades 5-8), the head of Upper School reports jointly to Assistant Head of School, and Head of School, Meredith Legg who joined the Winsor community in July 2025. The next head of Upper School will bring energy, sound judgment, curiosity, and a genuine delight in working with young people, while thoughtfully guiding the Upper  School through a period of meaningful opportunity and change.

OPPORTUNITIES AND CHALLENGES

Build a more intentional and coherent student experience beyond the classroom. The head of Upper School will provide leadership for an integrated student experience, ensuring that advisory, leadership development, student organizations, and co-curricular programs contribute meaningfully to students’ growth and sense of belonging. The head of Upper School will partner with class deans and faculty to clarify the purpose and desired outcomes of advisory; continue to partner with the Wellness Department head to develop a coherent approach to leadership education and programming that provides students with meaningful opportunities to build confidence, judgment, collaboration, and a sense of responsibility; and facilitate creative connections throughout the city that allow students and faculty to even more fully leverage Boston’s many resources. Importantly, the head of Upper School will also be a visible, engaged, and joyful presence with students and a highly communicative and proactive resource for parents and families.
Create greater coherence across the Upper School and the broader 5–12 program
The head of Upper School will bring a calm, steady, and reassuring presence to the Upper School, offering measured responses, clear guidance, and sound judgment. Working closely with the head of Lower School, the head of Upper School will strengthen the  transition from Lower School to Upper School to create an even more seamless student experience across divisions. The head of Upper School will identify ways in which the organizational structure of the Upper School might evolve to more fully support the division’s goals and will foster effective collaboration with the assistant head of school, department heads, class deans, and other members of the leadership team. Honoring the  distinctive developmental needs of its students, the head of Upper School will ensure that the Upper School functions as an integral part of a unified 5–12 program, promoting clear communication, shared problem-solving, and coordinated decision-making.

Support, develop, and inspire the faculty Winsor’s excellent and long-tenured faculty bring deep expertise, creativity, and a strong commitment to their students. The next head of Upper School will partner with department heads in faculty evaluation and professional  growth, support generative conversations about curriculum and pedagogy (including the use of AI), and build trust by creating the conditions in which faculty feel heard, supported, inspired, and energized by the work.

Bring focus and energy as a thought-partner to the head of school and senior leadership team in shaping Winsor’s next strategic plan The next head of Upper School will be an important thought-partner to the head of school and senior leadership team as Winsor develops and implements a new strategic plan—work that will kick off in spring 2027,
on the heels of the mission review that is currently underway. The head of Upper School will help translate strategic aspirations into meaningful action within the Upper School, working collaboratively to build alignment, establish priorities, and determine the pace and  sequence of change. Nuanced understanding of the curricular and co-curricular dimensions of a complex Upper School and particular alignment with Winsor’s commitment to educating young women; Deep knowledge of current and evolving best practices and innovation in Upper School curriculum, pedagogy, and student life;
Strong evidence of a personal and professional commitment to diversity, equity, inclusion, and belonging and a track record of shared ownership in nurturing a diverse and inclusive school community; Proven ability to lead thoughtful change while building faculty trust and community buy-in; Administrative experience supporting, supervising, and developing faculty with clarity, consistency, and care; A record of building systems that improve communication, alignment, decision-making, and follow-through; Demonstrated ability to navigate difficult conversations, engage in candid dialogue, and make thoughtful decisions in complex situations; Experience recruiting, developing, and retaining diverse, mission-aligned faculty; and The skill and willingness to teach one Upper School class each year.

Leadership Style and Personal Qualities:

Relational, approachable, and genuinely invested in the lives of students and colleagues;  Energetic and collaborative, building trust, shared ownership, and collective momentum;  Calm, flexible, and responsive, with the capacity to troubleshoot effectively in real time and the organizational fluency to manage multiple streams of information and respond to situations as they emerge; Creative and resourceful, approaching challenges with intention, humility, curiosity, and a growth mindset; Strategic and discerning, able to translate ideas into focused, purposeful action; Warm and credible partner to sophisticated, highly engaged parents; Generous-minded community builder who values relationships, traditions, and institutional culture; and a sense of humor, playfulness, energy, and joy in the daily rhythms of the school day.

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