Director of Development

About Free Spirit Community Arts + Media

Free Spirit Community Arts + Media (“Free Spirit”) partners with young storytellers to transform media and society. We do this through our holistic programming which focuses on community-building, skill-sharing, and career and education pathways that support young people to envision and build their futures within the media industry and beyond. Free Spirit’s goal is to support young storytellers as they form robust and sustainable support systems, gain the skills needed to pursue employment in their creative fields, and understand the powerful and important gifts they bring to the world.

Free Spirit’s media arts education and creative workforce investment programs are designed to break down barriers to access, success, and leadership for emerging media makers and storytellers from Chicago’s West and South sides. Our collectively realized organizational values are: Young Artist Leadership, Creativity, Belonging, Transformation & Intergenerational Collaboration.

Position Overview

Are you a visionary, equity-driven leader and fundraiser who believes in the power of young people to drive social change? Free Spirit Media seeks a Director of Development to spearhead our resource mobilization strategy with a community-centric approach. The Director of Development is the primary architect of Free Spirit’s financial sustainability. This role provides high-level strategic management of all revenue streams. You will serve as a thought partner to the Executive Director, ensuring that our fundraising efforts are not just a means to an end, but an authentic extension of our mission to partner with young storytellers to transform media and society.

Core Responsibilities

Strategic Leadership & Revenue Growth

• Fundraising Strategy: Design and lead a multi-year comprehensive fundraising plan to meet or exceed an annual goal of $1.5M+, diversifying revenue across individual major gifts, corporate partnerships, and private/public foundations
• Organizational Strategy: Partner with the Executive Director and Free Spirit staff to align development goals with programmatic needs and long-term organizational health
• Board Engagement: Serve as the primary liaison to the Board’s Development Committee; coach Board members in their role as ambassadors and solicitors

Major Gifts & Individual Giving

• Portfolio Development & Management: Develop and manage a portfolio of high-capacity donors, moving them through the stages of identification, qualification, cultivation, solicitation, and stewardship
• Campaign Oversight: Strategize annual appeals and peer-to-peer initiatives, shifting focus from “transactional” giving to “transformational” community-centric philanthropy
• Legacy & Planned Giving: (New) Begin the foundational work for long-term sustainability through multi-year pledges and planned giving programs

Institutional Partnerships & Grant Management

• Grant Strategy: Direct the institutional giving pipeline, working with a contracted grant writer to ensure all proposals are high-quality, mission-aligned, and reflective of youth voices
• Grant Writing: Manage a portfolio of grant reports and renewals outside of those produced by the grant contractor
• Grant Management: Maintain the grant calendar, including the cultivation of new prospects, the tracking of deadlines and timely acknowledgements
• Funder Relations: Maintain high-level relationships with program officers at major foundations and government agencies

Integrated Communications & Community Narrative

• Brand Alignment: In partnership with the Operations & Communications Manager, ensure all external messaging (annual reports, social media, website) reinforces the dignity and agency of our young storytellers
• Events as Cultivation: Oversee the strategy for the annual fundraiser, ensuring that the event serves as powerful cultivation tool as well as a successful revenue source

Team Management & Mentorship

• Staff Supervision: Manage and mentor the development team (Associates and Interns), fostering a culture of professional growth, accountability, and intergenerational collaboration
• Budgetary Oversight: Build and manage the Development Department budget with high integrity, providing regular reports and forecasts to the Executive Director and Board

Qualifications & Requirements

• Experience: 7+ years of progressive fundraising experience, with at least 3 years in a leadership or management role (social justice nonprofit and/or arts education experience preferred)
• Strategic Vision: Proven track record of growing a donor base and successfully soliciting five- and six-figure gifts
• Equity Mindset: Deep understanding of Community-Centric Fundraising (CCF) principles and a commitment to dismantling traditional, power-imbalanced philanthropy models
• Communication: Exceptional storytelling skills; ability to translate complex social issues into compelling cases for support
• Writing & Analysis: High-quality writing and spoken communication skills, with a deep understanding and analysis of systems of power and oppression and a commitment to systems change
• Technical Proficiency: Advanced experience with Salesforce or similar CRM to drive data-informed decision-making
• Leadership: A mentorship-based leadership style that empowers staff and respects the inherent agency of young people
• Location: Must be based in the Chicago area