Position Overview

The Director of Annual Giving is a strategic fundraising leader who will shape the future of philanthropy at The Winsor School. Reporting to the Chief Advancement Officer, this highly visible role provides leadership for the Winsor Fund, guiding annual giving strategy, volunteer engagement, donor stewardship, and a talented advancement team. Building on the momentum of a historic comprehensive campaign, the Director will strengthen donor participation, cultivate leadership-level annual gifts, and develop innovative, data-informed fundraising initiatives that inspire lifelong engagement across the Winsor community.

What You’ll Do

• Lead the strategic vision and execution of the Winsor Fund, driving annual fundraising performance, donor participation, and philanthropic growth.
• Manage and mentor the annual giving team while partnering with school leadership, trustees, faculty, volunteers, and Advancement colleagues.
• Develop and execute multi-channel fundraising campaigns, including Giving Day, direct marketing, stewardship initiatives, and reunion giving.
• Cultivate, solicit, and steward a portfolio of leadership annual giving donors while strengthening the major gift pipeline.
• Leverage fundraising analytics, donor segmentation, and emerging technologies to inform strategy and maximize fundraising success.

What You’ll Bring

• Bachelor’s degree and at least five years of fundraising or development experience, including annual giving and frontline fundraising.
• Demonstrated success leading fundraising programs, managing staff, and engaging volunteers.
• Proven ability to cultivate, solicit, and close leadership annual gifts while building strong donor relationships.
• Excellent communication, presentation, organizational, and project management skills.
• Experience using fundraising databases such as Raiser’s Edge (or comparable CRM) and applying data to fundraising strategy.

Compensation & Benefits

• Salary range of $120,000–$165,000.
• Opportunity to join one of the nation’s leading independent schools for girls during an exciting period of philanthropic momentum.
• Work alongside an experienced leadership team while helping shape the future of fundraising at a nationally recognized institution.