Job Description

About Winsor School

Founded in 1886, The Winsor School is an independent girls school serving students in grades five through twelve. Located in Bostons Longwood Medical and Academic Research area, the school offers a rigorous collegepreparatory 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 socioeconomic diversity through inclusive curriculum, diverse programs, and community engagement.

Role Overview

The Chief Advancement Officer (CAO) will lead a comprehensive advancement programincluding annual giving, major and planned gifts, alumnae and parent engagement, donor stewardship, volunteer leadership, campaign planning and execution, and advancement operationsto expand philanthropic support in alignment with Winsors 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.

Key Responsibilities

• 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 bestpractices 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.

Qualifications & Attributes

Professional Experience & Skills

• At least 10 years of progressively senior leadership in advancement, development, or fundraisingideally within an independent school, higher education, or missiondriven nonprofit.
• Demonstrated success in designing and executing major gifts, annual funds, planned giving, and capital campaigns, especially in a competitive urban independentschool environment.
• Proven capacity to cultivate, solicit, and steward transformational gifts and build longterm 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 and Organizational Abilities

• Strategic thinker able to align philanthropic efforts with institutional priorities and translate vision into measurable outcomes.
• Strong projectmanagement 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.

Personal Attributes

• Collaborative, inclusive, transparent leader grounded in integrity and empathy.
• Deep belief in Winsors mission and girls education.
• Strong talent for identifying, selecting, retaining, and inspiring advancement professionals.
• Professionalism, discretion, and confidentiality.
• Ability to navigate complexities and ambiguity within the community.
• Motivated, flexible, problemsolver with innovation commitment.
• Proficiency in inspirational presentationmaking.
• High emotional intelligence, cultural competency, and commitment to inclusion.
• Active listener with optimistic, curious approach.
• Warm, energetic, confident presence as public face.
• Active engagement across campus and community.
• Growth mindset and ongoing professional learning.
• Ability to inspire generosity through relationships, storytelling, and mission.

Education

• Bachelors degree required; advanced degree in relevant field strongly preferred.

Work Environment & Complexity

• Services involve managing complex projects, collaborating across leadership, operating in a typical office setting.
• Fastpaced environment requiring flexibility and proactive problem solving.

Physical Demands

• Must see, hear, speak, understand English, use computer; requires standing and walking, including stairs.

Travel

• Overnight travel expected; valid drivers license required.

Benefits

Winsor offers a competitive salary and a strong benefits package for employees.

Application Process

To apply, submit a cover letter, rsum or CV, and a list of professional references (use the provided link). Use the RG175 website. For inquiries contact James E. Pattison (jpattison@rg175.com).

EEO Statement

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 reflects the diversity of the Boston area.

Additional Application Information

Personal Information

• First name
• Last name
• Email
• Address
• City
• State
• Zip code
• Country
• Phone number

Attachments

• Resume
• Cover letter

Other Information

• Proof of legal right to work in the U.S. (Yes/No)
• Visa sponsorship requirement (Yes/No)
• How did you hear about this position?
• Years of experience in an independent school setting?
• List software programs, databases, and technical skills.
• Highest level of completed education.
• Prior relationship with The Winsor School?

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