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Director of Annual Giving

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The Winsor School

Director of Annual Giving

The Winsor School

Onsite Boston, Massachusetts
Apply Now Leadership Profile

For nearly 140 years, The Winsor School has been one of the nation’s premier independent schools for girls, preparing intellectually curious and motivated students in grades 5–12 to think critically, lead with integrity, and pursue lives of purpose. Located in Boston’s Longwood academic and medical community, Winsor combines a rigorous academic program with an enduring commitment to innovation, belonging, and the development of confident young women ready to shape the future.

Today, Winsor is entering an exciting new chapter. Under the leadership of Head of School Meredith Legg and Chief Advancement Officer Emily Gurry, the school is building on the remarkable success of its historic Winsor Leads campaign while preparing for the next era of philanthropic engagement. With more than $80 million raised toward a $100 million goal, strong alumnae participation, and significant investment in student support, faculty excellence, and endowment growth, Winsor offers an exceptional opportunity for a fundraising leader to help sustain this momentum and shape the future of girls’ education.

The Opportunity

As the institution prepares to complete its landmark comprehensive campaign and transition into its next phase of philanthropic growth, the school seeks a strategic leader who can elevate annual giving from an already successful program into an even more dynamic engine for long-term donor engagement and institutional support.

Reporting directly to the Chief Advancement Officer, this leader will guide the future direction of the Winsor Fund while expanding participation, strengthening donor loyalty, and building innovative strategies that connect every segment of the Winsor community to the school’s mission.

The Director will oversee every aspect of annual giving, from multi-channel fundraising campaigns and Giving Day strategy to volunteer engagement, leadership annual gifts, stewardship initiatives, and data-informed fundraising.

For an experienced annual giving professional, Winsor offers the chance to make a lasting impact at one of the country’s most respected independent schools.

The salary range for this position is $120,000–$165,000.

The Winsor School

Past searches and placements for The Winsor School

  • Director of Major Gifts

The Lindauer Team Leading This Search

Contact Us Directly

Jackie Sullivan

Jackie Sullivan

Senior Vice President
Alexandra Barber

Alexandra Barber

Senior Consultant
Dianne Cullinane

Dianne Cullinane

Senior Search Administrator and Executive Assistant

    Apply Now

    To apply for this position, complete this form and upload your resume. Your information will be kept confidential.








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        By admin|2026-09-23T21:28:15-04:00July 29, 2026|Comments Off on Director of Annual Giving

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        A respected professional services leader and a sought-after advisor to organizations across the nonprofit sector, Jackie Sullivan draws on an extensive toolkit of problem-solving strategies to consistently deliver innovative solutions and actionable recommendations for her clients. With a focus on tactical implementation, big-picture thinking, and high-touch relationships with stakeholders, she has earned the trust of numerous organizations engaged in life-changing work around the world.

        Known for approaching challenges with tenacity and determination, Jackie brings a wealth of experience in independent school, higher education, and global and social nonprofit leadership and consulting that positions her as the ideal partner for recruiting top-tier talent.

        Expertise

        Jackie’s core strengths lie in her profound understanding of organizations and their operational intricacies, coupled with her ability to assess and fulfill the unique needs of development offices within these institutions. Her deep well of knowledge regarding the inner workings of institutions allows her to navigate their complexities with precision and insight, while her breadth of experience gives her an industry-level perspective.

        Jackie has partnered with the full range of independent schools, including boarding and day schools, faith-based schools, single-gender schools, and specialty programs, as well as an array of higher education, global, and social nonprofits.

        Experience

        Jackie’s experience as a seasoned development officer within independent schools and higher education, as well as her extensive experience as a strategic consultant partnering with these institutions, uniquely positions her as a top expert and advisor for leaders in education.

        Before joining Lindauer, Jackie honed her expertise in navigating the complexities of a range of educational and nonprofit environments working both in-house in development offices at institutions like Syracuse University, the Pingry School, and Delbarton School as well as externally as a principal consultant at Graham-Pelton, a global leader in nonprofit consulting.

        Her commitment to the field includes serving on the Board of Directors for The Giving Institute and, previously, on the board of the Morris Education Foundation.

        Education

        Jackie holds a BA in Math and Psychology from Syracuse University.

        As a Senior Consultant at Lindauer, Alexandra Barber brings 10+ years of experience in higher education fundraising, development, and enrollment.

        Prior to joining Lindauer, Alex spent three years at UNC Asheville in a variety of roles within University Advancement and the Chancellor’s Office. Most recently as Executive Assistant to the Chancellor and Chief of Staff, Alex worked with the University leadership and the Board of Trustees to carry out major strategic initiatives including a comprehensive fundraising campaign, institutional revitalization plan, and campus master plan. As Assistant Director of Donor Relations, she was charged with thinking creatively to improve stewardship and create long-term, sustainable solutions for Donor Relations. Among the results were the creation of more customized donor experiences, an implementation of the divisions first-ever major donor satisfaction survey, and the creation of a six-month campaign feasibility/readiness study comprised of 20 virtual focus group sessions with 250 donors and community members.

        Before her tenure at UNC Asheville, Alex spent five years in Graduate Admissions and Recruitment for the Milken Institute School of Public Health at George Washington University, improving the campus visit experience and increasing enrollment across 30+ graduate degree programs through personalized recruitment strategies.

        Alex graduated with a Bachelor’s degree in Mass Communications from the University of South Florida and has a Master’s degree in Higher Education Administration with a focus in finance and policy from George Washington University.

        As Senior Search Administrator and Executive Assistant, Dianne Cullinane acts as the liaison between Lindauer clients, candidates and consultants. She provides high-level strategic coordination and detailed administrative, client service and communications support to facilitate each search, balancing an array of clients and assignments.

        Dianne brings over 35 years-experience as an Executive Administrative Assistant, with a decade of those years spent in higher education fundraising. Dianne began her time at Simmons in the President’s Office, working with the Board of Trustees, Corporators and President’s Council. She learned all aspects of fundraising as the Executive Assistant to the Vice President of Advancement at Simmons College while earning her Bachelor’s degree. She also served as Associate Director of Institutional Programs and Special Events in her tenure at Simmons, handling all the strategy, planning and implementation of all institutional events. Known for her high level of organization and relationship-building, she facilitated cross-campus collaboration, helped build external visibility for the university’s brand, and identified opportunities for new events and expanded audience engagement. Before Simmons, Dianne worked at Blue Cross Blue Shield of Massachusetts supporting the Senior Vice President of Corporate Relations, at Choate Hall & Stewart in the corporate legal arena, and in the Human Resources office of The Ritz-Carlton Boston.

        Dianne holds a Bachelor’s in Psychology from Simmons University in Boston, Massachusetts.

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