Director, Advancement Strategy & Major Gifts

About CSS

Center for Supportive Schools (CSS) is a fast-paced, collegial, and team-oriented organization wholly committed to helping schools become places where students want to be. CSS is driven by the vision that one day, all students will thrive in schools that graduate them prepared for the rigors of college and lives filled with meaningful work, active citizenship, and personal fulfillment.

Our work directly addresses student disengagement, a root cause of diminished academic performance, students dropping out of school, and other high-risk student behaviors. Founded in 1979, we are a national organization currently impacting 65,000 students annually and committed to supporting every K-12 school in the country.

We know that we can only be truly mission-oriented by first building a safe, supportive, engaging, and inspiring internal culture. Thus, we focus on creating the conditions for staff to bring the full weight of their brilliance, skills, and past experiences, and to thrive personally. We work to ensure that all staff feel accepted, valued, affirmed, connected, safe to grow, and encouraged to advocate for progress.

For more information, please visit www.supportiveschools.org.

The Role

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).

Key Job Responsibilities

Major Gifts Strategy & Execution

• 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

Advancement Strategy & Leadership

• 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

Relationship Management & Donor Engagement

• 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

Collaboration & Internal Partnerships

• 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 understand impact stories and translate them into donor-facing opportunities for engagement and case for investment
• Coordinate with Finance to ensure accurate gift tracking and reporting

Qualifications and Experience

Required Qualifications/Experience:

• Bachelor’s degree in nonprofit management, business, communications, or related field
• 5–7+ years of progressive experience in fundraising, major gifts, or advancement leadership
• Demonstrated success securing $400,000 or more annually
• Proven track record of cultivating and closing major gifts of $25,000+
• Strong strategic planning, communication, and relationship-building skills
• Demonstrated ability to leverage digital platforms, thought leadership and professional networks to support donor engagement and pipeline development.
• Proficiency with CRM and donor management systems (Salesforce)

Location

The Director of Advancement Strategy & Major Gifts is a hybrid role and will require travel nationally, with frequent travel to the following major markets: Atlanta; Boston; Los Angeles; New York City Metropolitan Area; San Francisco/Oakland Bay Area; Washington, DC Metropolitan Area; among others.

Preferred Qualifications/Experience:

• Experience in capital campaigns or long-term fundraising initiatives
• Familiarity with fundraising research and campaign platforms (Classy and iWave)
• AI-fluency—understands and explores the impact of generative AI tools and their impact on fundraising efforts and messaging
• Master’s degree or CFRE certification

Core Competencies

• Strategic Planning & Execution
• Donor Relationship Management
• Communication & Storytelling
• Data-Driven Decision-Making
• Collaboration & Leadership
• Goal Orientation & Accountability
• Confidentiality & Professionalism

Performance Metrics

• Achievement of $400,000–$600,000 in secured gifts annually
• Growth of major gift donor portfolio
• Retention and increased engagement of donors
• Advancement of major gifts strategy and measurable pipeline development

Work Environment/Physical Requirements

• Prolonged periods of sitting at a desk and working at a computer, including participating in virtual videoconference meetings
• Communicating with others in writing and verbally to exchange information
• Traveling long distances by plane/car

To Apply

Interested applicants are requested to apply by emailing a cover letter and CV/résumé to resumes@supportiveschools.org. Please include (1) the title of the position in the subject line of your email and (2) where you found the position posting in your cover letter. If possible, please email all documents in PDF format.

Center for Supportive Schools is an equal opportunity employer committed to inclusive hiring.

Compensation and Benefits

The anticipated starting date for this position is April 2026. The annual salary range for this position is $75,000 - $85,000 per year.

CSS offers the following benefits:

• Comprehensive and competitive benefits plan, including health, dental, vision, flexible spending accounts, health reimbursement accounts, commuter and transit accounts
• 403(b) plan with employer match
• Generous paid time off
• Paid holidays and winter break
• Flexible work option based on job role eligibility
• Employee Assistance Program
• Reduced schedule on Fridays during summer months
• Phone stipend