Director, Strategy & Major Gifts

The Center for Supportive Schools (CSS) is in search of a senior fundraising leader who will be responsible for developing, managing, and executing enterprise-wide major gifts and advancement strategies that will drive major philanthropic investments to support the mission and long-term sustainability of the organization. In this role, the Director of Advancement Strategy & Major Gifts will partner closely with the CEO, in ensuring that CSS is positioned as a celebrated organization poised for transformative philanthropic investments.

This colleague will provide leadership for and execution of the major-gift strategy, cultivating high-value donor relationships, and building and providing oversight of a portfolio of prospects—both individual and institutional, qualified to make gifts of $25,000 and above. With direct support from the Executive Advisor to the Office of the CEO, the Director of Advancement Strategy & Major Gifts will also partner closely with the Manager of Advancement Operations and Annual Fund(s) to meet and exceed philanthropic revenue targets for CSS.

The ideal candidate is known for their meticulous attention to detail, engaging and inspiring connections with donors and champions, and excellence in execution of initiatives and campaigns. This leader will have demonstrated success in securing major gifts in the nonprofit space, and deep alignment with and connection to education and youth development causes. As a hybrid/remote colleague, there will be some travel required to support the CEO and trustees in specific markets (Atlanta;
Boston;
Los Angeles;
New York City Metropolitan Area; San Francisco/Oakland Bay Area; Washington, DC Metropolitan Area; among others).

• Develop and implement a comprehensive major gifts strategy aligned with organizational priorities
• Manage and continuously refine a portfolio of ~75–125 qualified major gift prospects with the capacity to give $25,000+
• Conduct regular donor cultivation, solicitation, and stewardship activities to meet or exceed annual philanthropic revenue targets
• Create individualized cultivation plans and solicitation strategies for top prospects
• Collaborate with executive leadership and trustees to support high-level donor engagement, including, but not limited to the following: network mapping and connections; special events and acknowledgments; fulfillment of incentives at varying giving levels; among others
• Provide leadership and expertise in strategic planning initiatives that strengthen long-term fundraising capacity and pipeline development
• Partner with the CEO, Trustees, and program leaders to identify mission‑aligned funding opportunities and prepare supporting materials to equip organizational leaders for engagement with potential funders
• Use data‑driven insights to shape donor engagement strategies and ensure a healthy pipeline of prospects
• Track giving trends (within the organization, education field, and especially across peer institutions), assess fundraising performance, and adapt strategies to ensure goal attainment

• Build meaningful, lasting relationships with donors, securing multi‑year commitments where possible
• In partnership with the Executive Advisor and Managing Director of External Affairs & Engagement, craft compelling donor materials, proposals, and impact reports
• Ensure and track regular touchpoints and deliver exceptional stewardship that deepens donor commitment
• Provide high quality data inputs, management, and reporting to ensure accurate and timely summary of progress to goal achievement for the CEO and for reporting to trustees
• Identify and suggest key events and opportunities for executive leadership presence, including attending donor meetings, community events, and other strategic engagements

• Work closely with External Engagement team to align messaging and donor engagement collateral, including design projects/visual representation of key initiatives, giving levels, campaigns, among other tools for consistency of storytelling and impact
• Partner with program staff to…