Crystal Hayling found her way into philanthropy in an old-school way: by answering a classified ad in the Los Angeles Times. The new Los Angeles Women’s Foundation was seeking its first program staffer, and Hayling, a recent college grad, got the job.

This was in the early years of the women’s funding movement, which was trying to bring women together across race and class to advance gender justice in their communities. Women’s funds aimed to challenge the philanthropy field and make it better and more relevant to more people.

Over the next three decades, Hayling has remained in positions on the cutting edge of philanthropy and has pushed against the status quo. She has led initiatives at organizations such as the California Wellness Foundation and California Health Care Foundation on a wide swath of causes, from health-care access and violence prevention to climate and racial justice. Hayling has not only diversified the leadership ranks in philanthropy by virtue of being a Black woman from the South; she also has changed the sector by continually challenging its credo and conduct with grantees.

“It’s been a big surprise to me that I’ve had a career in philanthropy,” she says. “In every job that I’ve had, I’ve been aware that I might at some point, say or do something that might result in me no longer having that job. And yet it felt important to know that I was the voice for the people who weren’t in the room.”

This spring, she will retire from her post as executive director of the Libra Foundation, where she spent six years leading the San Francisco-based family foundation in its support of groups working to build grass-roots power. During her tenure at Libra, Hayling launched the Democracy Frontlines Fund, a racial justice initiative that has catalyzed $74.5 million in commitments to Black-led grassroots groups and challenged philanthropy to think bigger about how to break down power dynamics to achieve meaningful and lasting change. Colleagues say she was ahead of the curve in calling for philanthropy to embrace trust-based practices and modeling that work at the foundations she led.

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