Leigh Bailey
Director of Advancement @Sasha Bruce Youthwork
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WORK HISTORY
Director of Advancement @Sasha Bruce Youthwork
DC, US
Lead and execute comprehensive advancement strategies that drive individual giving, institutional philanthropy, and community engagement to achieve organizational revenue goals. Oversee the annual fund, mid-level and major gifts, and signature events—including the annual Gala—to deepen donor relationships and maximize philanthropic impact.• Manage a portfolio of key donors and prospects while mentoring advancement staff and fostering a collaborative, accountable team culture. Partner across departments to align advancement goals with program, communications, and finance priorities, ensuring mission-driven outcomes and operational excellence.• Advance institutional fundraising by overseeing the development and submission of foundation, corporate, and select government proposals. Engage Board members and senior leadership as active partners in fundraising, cultivating strategic relationships to sustain long-term partnerships and organizational growth.
EDUCATION
Institute for Multi-Sensory Education
Certificate - 30-Hour Orton-Gillingham Multi-Sensory Training, Orton-Gillingham
American University
Master of Arts, Arts Management
LADO
TESOL Certification, Teaching ESL
College of Charleston
Bachelor of Arts - BA, Art History
Center for Inspired Teaching
Elementary Education and Teaching
ABOUT LEIGH BAILEY
I\'m an experienced expert in securing funds from foundations and corporations for nonprofit organizations and a strong advocate of radical kindness in leadership and practice. With over 20 years of experience in driving institutional fundraising, marketing, and communications strategies, I have helped mission-driven organizations raise more than $20 million through foundation, corporate, and government support. I bring deep experience across every aspect of the development cycle, from grant writing to stewardship to strategy.At Sasha Bruce Youthwork, I\'ve helped grow institutional revenue from to over $1.1 million in just three years by strengthening relationships with funders, leading multi-year proposals, and aligning messaging across program teams. I also support internal communications and storytelling—writing donor communications, reports, web content, and strategic materials for campaigns and events.As a leader, I\'m committed to preparing the next generation of diverse nonprofit leaders—creating space, support, and mentorship for professionals whose perspectives and contributions are vital to a more equitable sector. I thrive in fast-moving, collaborative environments and bring a hands-on, get-it-done approach to every project. Whether launching a new campaign, closing a budget gap, or mentoring a new team member, I offer both strategic vision and practical experience.🧩 Skills: Institutional Fundraising | Grants Strategy | Funder Stewardship | Proposal & Report Writing | Internal Communications | Campaign Messaging | Cross-Team Collaboration | Budgeting Recent Wins:• Raised over $20 million in institutional funding over the course of my career• Grew foundation and corporate giving from $313K to $1.1M at Sasha Bruce Youthwork• Managed grant portfolios of $900K–$2M across multiple organizations• Secured six-figure grants from Capital One, CareFirst, and TD Charitable Foundation
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