Chief Advancement Officer

The Winsor School | Boston, Massachusetts

The Opportunity

Since its founding in 1886, the Winsor School has been a defining presence in Boston’s independent-school community, known for its rigorous academic program for girls in grades 5-12, its urban location, and its deep commitment to preparing young women for lives of purpose, service, and leadership. Drawing from its legacy and mission—“to prepare young women to pursue their aspirations and contribute to the world”—Winsor 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 mission-aligned 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 nation’s premier independent schools for girls. The CAO will lead a comprehensive, integrated advancement program—encompassing 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 Winsor’s strategic vision.

Importantly, Winsor is currently in the final phase of its Winsor Leads Campaign, a $100-million 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 school’s philanthropic momentum. The ideal candidate will bring a distinguished track record in fundraising and advancement leadership—especially within independent schools or mission-driven nonprofits, a collaborative mindset, and the ability to tell a compelling story about Winsor’s mission and impact. As a member of the senior leadership team, the CAO will be instrumental in securing support for Winsor’s next phase of institutional strength and programmatic excellence.

History

Founded in 1886 by Mary Pickard Winsor, who began a six-month school for eight girls in Boston’s Back Bay, Winsor has grown from its modest origins into a distinguished college-preparatory institution for girls in grades 5 through 12. Miss Winsor’s founding purpose was to prepare young women to be self-supporting, competent, responsible, and generous-minded—an ethos that continues to shape Winsor’s identity and program. The school relocated in 1910 to its current location in the Longwood neighborhood, placing it at the nexus of Boston’s 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.

The Program

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 co-curricular 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 school’s city-central 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 5–8) and Upper School (grades 9–12) 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 doers—applying, creating, and leading. One senior faculty leader, in describing the unique opportunity an all-girls school offers said, “In our classrooms, we don’t say, ‘I might be wrong, but…’ Girls here learn not to explain away their intellect.” Learn more about Winsor’s academic program and curriculum here. 

Community and Inclusion

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. 

Athletics

At Winsor, athletics are not an afterthought; they offer students a daily context for discipline, teamwork, resilience, and leadership. Students in grades 6–12 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.

Arts

Winsor’s arts program ensures that creativity, self-expression, 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. 

Signature Programs

Winsor doesn’t stop with the “typical” offerings—it builds signature experiences that align with its urban Boston location, all-girls mission, and commitment to depth and discovery. The campus brings together students across grades 5-12 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 real-world 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.

Fast Facts

• Founded: 1886 by educator and innovator Mary Pickard Winsor

• Location: Boston, Massachusetts, in the Longwood Medical and Academic Area, adjacent to the Museum of Fine Arts and many leading universities and research centers

• Enrollment: Approximately 475 students in Grades 5–12

• Student-to-Faculty Ratio: 7:1

• Average Class Size: 13 students

• Faculty: About 70 full-time teachers, more than 80 percent with advanced degrees

• Diversity: Roughly 62 percent students of color; over 50 towns and cities represented

• Financial Aid: 25 percent of students receive need-based aid; total aid exceeds $6 million annually

• Campus: 7 acres with 215,000 square feet of academic, arts, and athletic facilities—including the Lubin-O’Donnell Center for Performing Arts, Athletics, and Wellness

• Athletics: 14 team sports, 2 interscholastic sports, and 2 club sports; member of the Eastern Independent League (EIL) and NEPSAC

• Arts: Comprehensive visual and performing arts program featuring the Goel Theater, Baldwin Recital Hall, and Koppel-Haynes Music Lab

College Matriculation: 100 percent of graduates attend four-year colleges and universities; alumnae pursue leadership across the arts, sciences, math, journalism, medicine, public service, business, education, and beyond.

Head of School and the Board of Trustees

Head of School

Meredith Legg brings a uniquely powerful blend of engineering mindset, educational innovation, and girls-school 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 STEAM-team lead, and even as a teacher of physics, engineering, and environmental science. Meredith holds a B.S. in civil engineering from Iowa State University and a Ph.D. in civil engineering from Cornell University. Before entering education leadership she worked as a structural engineer. She frames her leadership through listening and community-building, describing school leadership as “much like great teaching… it starts with a deep curiosity about how and why people come together to do inspired work; builds the trust and support of a community; and consistently inspires reflection and growth.” 

Board of Trustees

Supporting Meredith is the school’s active and engaged board of trustees, whose stewardship is anchored by President of the Winsor Corporation Allison Kaneb Pellegrino ’89, P’21, ’22. A Winsor alumna herself, Allison has brought both institutional loyalty and strategic acumen to the role, having chaired the board since 2015. Under her leadership the board has guided the school through a historic campaign, elevated alumnae engagement, and renewed focus on access, diversity, and future-ready advancement.

Together, Meredith, Allison, and the broader Board of Trustees — are positioning Winsor for its next chapter of growth: refining its signature program; powering philanthropic momentum; strengthening faculty, student, and alumnae engagement; and telling the story of an historic, inner city girls’ school, rooted in tradition and boldly forward-looking.

Living in Boston

Located on an urban campus in the heart of Boston’s Longwood Medical Area, Winsor offers an extraordinary backdrop for the student and professional experience. The school’s location places it in one of the nation’s richest cultural, academic, medical, and research ecosystems, with neighbors including major universities, such as Boston College, Boston University, Harvard University, MIT, Northeastern University, and Tufts University; world-class museums; performance venues; and dynamic neighborhoods. Living in Boston means access to an unparalleled mix of city amenities, green space, public transportation, and historic neighborhoods. For faculty and staff, this context offers intellectually stimulating environments, rich professional networks, and deep community engagement opportunities. Joining Winsor means engaging in this exciting, urban educational environment while contributing to a community that celebrates curiosity, leadership, and inclusion.

Opportunities, Challenges, and Key Responsibilities for the Chief Advancement Officer

The Winsor School seeks a visionary, strategic, and collaborative chief advancement officer to partner with Head of School  Meredith Legg, the board of trustees, and the senior leadership team in advancing the next phase of Winsor’s educational mission. Building on a legacy of excellence and a strong financial foundation, the CAO will play a vital role in strengthening the culture of philanthropy, deepening community engagement, and ensuring that Winsor has the resources and agility to respond boldly to emerging opportunities and challenges.

Working in concert with the head of school, the CAO will help articulate and fulfill a shared vision for philanthropy that is mission-driven, inclusive, and aligned with Winsor’s enduring commitment to empowering young women to lead lives of purpose, courage, and joy. By amplifying the stories that define the Winsor experience, the CAO will inspire alumnae, parents, and friends to invest in the school’s continued success.

Winsor’s next chief advancement officer will bring a deep appreciation for girls-only education, a record of strategic and successful fundraising, and a passion for mentoring and empowering teams. A leader who is both disciplined and empathetic, this individual will elevate collaboration across advancement, communications, and engagement functions; foster alignment with admissions and academic leadership; and build a culture defined by shared purpose, trust, and accountability.

A seasoned fundraiser and team builder, the CAO will be energized by the opportunity to design and execute the next generation of Winsor’s advancement strategy. The successful candidate will be a confident relationship-builder, an exceptional listener and communicator, and an inspiring advocate for the transformational power of girls’ education. In partnership with the head of school, board of trustees, and senior leadership team, the CAO will help define Winsor’s next set of institutional priorities—ensuring that philanthropy continues to shape the lives of students, faculty, and the broader Winsor community for generations to come.

Leadership and Governance

• Serve as a member of Winsor’s senior leadership team, contributing to institutional strategy, culture, and high-level decision-making.

• Lead, mentor, and inspire an advancement team of 10, cultivating a culture of collaboration, accountability, and professional growth while elevating sights and creating an organizational context for success.

• Partner closely with the head of school and board of trustees, staffing key board committees to both build an engaged, informed culture of philanthropy amongst trustees and volunteers and ensuring clear alignment of philanthropic priorities with institutional goals.

• Articulate and champion Winsor’s mission, vision, values, and strategic priorities in internal meetings and external forums.

• Represent and be a powerful voice for Winsor at external events, conferences, alumnae gatherings, and community functions, enhancing the school’s visibility and cultivating meaningful and productive relationships with major stakeholders.

• Remain current with advancement industry best-practices and trends, bringing new ideas and innovation to Winsor’s philanthropic efforts.

Fundraising and Advancement Strategy

• Lead the remaining execution of the comprehensive Winsor Leads Campaign—a $100 million initiative with over $75 million raised to date, ensuring a successful conclusion that celebrates the transformative impact of collective community generosity.

• Engage the head of school in building and enhancing key relationships with potential and current leadership supporters; provide strategy and coaching to create an exceptional donor experience. 

• Provide strategic leadership to all advancement functions: annual giving, major and planned gifts, capital campaigns, alumnae and parent engagement, donor stewardship, advancement operations, and volunteer leadership.

• Work with the head of school and trustees to identify, cultivate, solicit, and steward major donors and key philanthropic partners aligned with Winsor’s mission and future vision.

• Enhance advancement operations to maximize efficiency—including prospect management, gift processing, data analytics and reporting, and donor communications—to ensure inspirational, transparent, and effective outcomes.

• Create and sustain volunteer structures and committees that engage alumnae, parents, and friends in meaningful philanthropic leadership and activity.

• Design and further develop a robust alumnae engagement program that strengthens lifelong relationships, inspires giving, and expands the network of many-generational donors and adds value to their lives.

• Serve as a compelling ambassador for Winsor’s mission, values, and philanthropic needs, inspiring investment in the school’s future.

Collaboration and Community Engagement

• Collaborate closely with admissions, communications/marketing, athletics, arts, and academic divisions to ensure that advancement strategies align with and bolster school?wide goals.

• Collaborate with Communications team to craft compelling stories, digital content, and campaigns that highlight Winsor’s impact and deepen donor engagement.

• Engage faculty, staff, students, alumnae, and parents in strengthening the culture of philanthropy, helping the community understand how individual and collective giving drives mission-critical work and ensures that Winsor is equal to the aspirations of its students.

• Model and uphold Winsor’s principles of equity, inclusion, generosity of spirit, and global responsibility in all advancement relationships and practices.

Winsor considers all qualified applicants for employment and does not discriminate on the basis of race, color, religion, identity, national origin, ancestry, age, sexual orientation, gender identity, and gender expression, or any other characteristic protected by law. The school is committed to having a faculty, staff and student body that reflect the diversity of the Boston Area. Ideal candidates are those with a demonstrated dedication to collaboration, innovation and student-centered education to apply.

Prior to submitting your resume for this position, please read it for accuracy. RG175 verifies academic credentials for its candidates and conducts a thorough review of candidates’ social media presence. Winsor will conduct thorough background checks prior to finalizing an offer. 

TO APPLY Start Date: July 1, 2026 |
The Winsor School is partnering with RG175 to identify exceptional candidates. Interested applicants should submit a cover letter that clearly articulates their interest in and fit for this role, a current résumé or CV, and a list of professional references (references will not be contacted without candidate permission). Please submit materials to the RG175 website. For inquiries about the search or to nominate a candidate, please contact: James E. Pattison: jpattison@rg175.com

Salary Range $250,000-$300,000

Qualifications & Attributes

Professional Experience & Skills

• At least 10 years of progressively senior leadership experience in advancement, development, or philanthropic fundraising—ideally within an independent school, higher education, or mission-driven nonprofit.

• Demonstrated success in designing and executing major gifts strategies, annual funds, planned giving, and capital campaigns, especially in a competitive urban independent-school environment.

• Proven capacity to cultivate, solicit, and steward transformational gifts, and to build long-term, meaningful donor relationships at scale.

• Experience managing advancement operations including prospect/donor databases, gift processing, reporting and analytics.

• Familiarity with innovative and aspirational alumnae and parent engagement programming that fosters lifelong connection and giving.

• Excellent written and oral communication and presentation skills, with an ability to convey an institution’s values, story, and philanthropic case compellingly to diverse audiences.

• Previous experience advising or working with boards and senior leadership teams on advancement strategy.

Strategic and Organizational Abilities

• Strategic thinker who can align philanthropic efforts with institutional priorities and translate vision into measurable outcomes.

• Strong project-management and organizational skills with the ability to manage multiple initiatives simultaneously in a fast-paced, urban setting.

• Analytical mindset and comfortable using data and insight to inform strategy, assess performance, and refine programs.

• Ability to bring creative thinking, innovation, and continuous improvement mindset to advancement work.

Personal Attributes

• Collaborative, inclusive, and transparent leader grounded in integrity and empathy.
  Deep belief in the mission and values of the Winsor School and in the power of girls’ education to change the world.

• Superior talent for identifying, selecting, retaining and inspiring outstanding advancement professionals—supporting, guiding and championing their growth.

• Professionalism and discretion; ability to maintain confidentiality.

• Ability to navigate the complexities and ambiguities of leading and inspiring others in a complex, deeply invested community.

• Motivated, flexible, problem-solver with a strong commitment to innovation.

• Comfort and proficiency with inspirational and informative presentation-making.

• A collaborative and collegial leadership style rooted in integrity, empathy, and discretion.

• High emotional intelligence, cultural competency, and strong commitment to community and inclusion.

• An active listener with a curious, optimistic approach.

• Warm, energetic, confident presence; comfortable as a public face of the school in donor and community settings.

• Interest in fully engaging in the school community—a visible and active member across campus. 

• Motivated, flexible, and solutions-oriented; embraces a growth mindset and ongoing professional learning.

• Ability to inspire others to give generously through authentic relationships, storytelling, and a clear sense of mission.
  
  

Education

• Bachelor’s degree required; an advanced degree in a relevant field (e.g., nonprofit management, business, communications, education) strongly preferred.

Work Environment & Complexity

• The duties and tasks associated with this position are both varied and complex. The role involves managing entire problems or projects, often requiring the direction of initiatives and the resolution of challenges through complex, precedent-setting solutions. Collaboration is essential, as is operating within a professional school setting. All functions are carried out in a typical office environment, with no known hazards. This is a fast-paced environment

Physical Demands

• The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this position, such as the ability to see, hear, speak and understand English and use a computer. This position is active and requires standing and walking, including stairs.

Travel

• Overnight travel will be expected in this position. A valid driver’s license is required.

In addition to a competitive salary, Winsor also offers a strong benefits package for employees.

This position statement is not designed to cover or contain a comprehensive listing of activities, duties or responsibilities that are required of the employee.  Other duties, responsibilities and activities may change or be assigned at any time with or without notice.

About The Winsor 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.

Connections working at The Winsor School