Winsor School
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.
Role Overview 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.
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 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.
Qualifications & Attributes Professional Experience & Skills
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 and Organizational Abilities
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.
Personal Attributes
Collaborative, inclusive, transparent leader grounded in integrity and empathy.
Deep belief in Winsor’s 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, problem‑solver with innovation commitment.
Proficiency in inspirational presentation‑making.
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
Bachelor’s 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.
Fast‑paced 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 driver’s license required.
Benefits Winsor offers a competitive salary and a strong benefits package for employees.
Application Process To apply, submit a cover letter, résumé 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?
#J-18808-Ljbffr
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.
Role Overview 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.
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 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.
Qualifications & Attributes Professional Experience & Skills
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 and Organizational Abilities
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.
Personal Attributes
Collaborative, inclusive, transparent leader grounded in integrity and empathy.
Deep belief in Winsor’s 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, problem‑solver with innovation commitment.
Proficiency in inspirational presentation‑making.
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
Bachelor’s 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.
Fast‑paced 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 driver’s license required.
Benefits Winsor offers a competitive salary and a strong benefits package for employees.
Application Process To apply, submit a cover letter, résumé 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
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?
#J-18808-Ljbffr