Chief Advancement Officer

About Winsor School

Founded in 1886, The Winsor School is an independent girls’ school serving students in grades five through twelve. Located in Boston’s Longwood Medical and Academic Research area, the school offers a rigorous college‑preparatory curriculum, commitment to diversity, inclusion, and a community of girls, alumnae, parents, faculty, and staff.

Winsor prides itself on creating a respectful and inclusive environment, supporting ethnic, racial, religious, and socio‑economic diversity through inclusive curriculum, diverse programs, and community engagement.

The Chief Advancement Officer (CAO) will lead a comprehensive advancement program—including annual giving, major and planned gifts, alumnae and parent engagement, donor stewardship, volunteer leadership, campaign planning and execution, and advancement operations—to expand philanthropic support in alignment with Winsor’s strategic vision.

The CAO partners closely with the head of school, board of trustees, senior leadership, faculty, alumnae, parents, and external stakeholders.

With flagship Winsor Leads Campaign ($100M definitive, >$75M raised), the CAO will spearhead the remaining execution and build major donor relationships.

• Serve as a member of the senior leadership team, contributing to institutional strategy and culture.
• Lead, mentor, and inspire the advancement team of 10, building a collaborative, accountable culture.
• Partner with the head of school and board to staff key board committees and align philanthropic priorities.
• Represent Winsor at external events, conferences, alumnae gatherings, and community functions.
• Stay current with advancement best‑practices and bring innovation.
• Oversee the complete execution of the Winsor Leads Campaign.
• Engage leadership supporters, provide strategy and coaching for donor experience.
• Provide strategic leadership to all advancement functions: annual giving, major and planned gifts, capital campaigns, alumnae and parent engagement, donor stewardship, operations, volunteer leadership.
• Identify, cultivate, solicit, and steward major donors and philanthropic partners.
• Enhance advancement operations: prospect management, gift processing, data analytics and reporting.
• Create volunteer structures and committees engaging alumnae, parents, and friends.
• Develop a robust alumnae engagement program to strengthen lifelong relationships.
• Collaborate with admissions, communications, athletics, arts, and academics to align advancement strategies.
• Craft compelling stories and digital content with Communications to deepen donor engagement.
• Model equity, inclusion, generosity, and global responsibility in all relationships.

• At least 10 years of progressively senior leadership in advancement, development, or fundraising—ideally within an independent school, higher education, or mission‑driven nonprofit.
• Demonstrated success in designing and executing major gifts, 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 build long‑term donor relationships.
• Experience managing advancement operations: prospect/donor databases, gift processing, reporting, and analytics.
• Familiarity with innovative alumnae and parent engagement programming that fosters lifelong connection.
• Excellent written and oral communication and presentation skills, conveying institutional values and philanthropic case compellingly.
• Previous experience advising or working with boards and senior leadership on advancement strategy.

• Strategic thinker able to align philanthropic efforts with institutional priorities and translate vision into measurable outcomes.
• Strong project‑management and organizational skills to manage multiple initiatives simultaneously.
• Analytical mindset, comfortable using data and insight to inform strategy, assess performance, and refine programs.
• Creative thinking, innovation, and continuous improvement mindset in advancement work.

• Collaborative,…