Retiring Philanthropy Leader Was Always ‘a Step or Two Ahead of the Pack’

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 the 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 grassroots 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.

Commitment to Racial Justice

When Hayling was growing up in Cocoa Beach and Fort Lauderdale, Fla., in the 1960s and 1970s, civil rights and racial justice were frequent topics of conversation at the family dinner table. And from an early age, she was taught that she had a responsibility to change the system.

Her father, a dentist and local civil-rights leader, led wade-ins, bringing Black people to segregated beaches, pools, and state parks to demand equal access. Her mother, a middle-school teacher, was active in the local teachers union.

Hayling’s father was severely beaten while monitoring a Ku Klux Klan rally. The family’s St. Augustine home was later shot up by Klansmen, killing the family dog and narrowly missing her mother, who was pregnant with Crystal at the time.

“We were raised to think about the ways that our lives could be committed to improving our democracy, improving the lives of folks we know in our community, just everyday working folks who didn’t really have equal access to opportunity,” she says.

Related Content

1. Special Report

   Grant Makers Join Together to Learn About — and Fund — Racial Justice

2. Video

   General Operating Support Is Vital to Advancing Equity, Strengthening Nonprofits, Say Leaders

Hayling, who went on to graduate from both Yale and Stanford, says she never shied away from utilizing both her elite education and her experience as a Black woman from the South in her work.

“I think about my parents and my lineage all the time when I’m making decisions in this field,” she says.

A Start-up Leader

Hayling has helped model trust-based approaches to philanthropy long before that became a sector buzzword. Trust-based philanthropy might include giving grantees multiyear general operating support, reducing the bureaucracy of applications and reporting requirements, and creating feedback loops to build more collaborative relationships and reduce the power imbalances between donors and beneficiaries.

“We didn’t call it trust-based philanthropy then, but it’s been an evolving way of incorporating more of the opinions and the say of people who are most impacted,” Hayling explains. “That’s kind of been how I’ve been approaching this work ever since.”

She considers herself a “start-up” specialist, and she has been part of the founding teams of a number of other grant-making organizations.

In the 1990s, as violent crime by young people surged in Los Angeles and other major California cities, she worked with the California Wellness Foundation to launch an initiative to reduce gun violence by reframing it as a public-health issue rather than as a criminal-justice concern.

That work was considered controversial at the time, she says. “Not only were we talking about funding what many people saw as dangerous young people — sometimes funding gang members to work on neighborhood peace initiatives — we were also naming easy access to cheap handguns as being a major vector of the public-health problem.”

At the California Health Care Foundation, she helped found and lead the Medi-Cal Policy Institute. That effort provided key policy support for major Medicaid expansion and the launch of the state’s first online Medicaid application. During that time, says Hayling, the institute conducted the first-ever survey of Medicaid beneficiaries in the state to assess what people thought about the program and incorporate their input into how it was run.

Under her leadership, the Blue Shield of California Foundation provided general operating support to community clinics throughout the state and launched a training program to help grow the pipeline of leaders to run those clinics. In addition, the foundation became a major funder of domestic-violence prevention, Hayling says, recognizing that for many women, their primary-care doctor was better positioned to spot signs of domestic violence than anyone else.

Robert Ross, CEO of the California Endowment, has known Hayling since they both entered health philanthropy more than two decades ago. “You could always depend on Crystal for clear-eyed sober analysis about the policy issues that were in front of us and what it would take to cross the bridge to universal health care in this nation,” Ross recalls.

She was also just fun to work with, he says. “She’s someone who took the work seriously but did not take herself too seriously.”

Hayling also worked at the Evelyn & Walter Haas, Jr. Fund, served as a senior adviser at the Marguerite Casey Foundation and as managing director of the Aspen Institute’s Environment Leaders Fellowship. She spent nearly eight years consulting for grant makers and nonprofits in areas such as strategic philanthropy, social entrepreneurship, and community engagement.

Jean Melesaine, Libra Foundation

“She’s one of the most important and inspiring foundation leaders of the last two decades,” says Phil Buchanan, president of the Center for Effective Philanthropy, where Hayling served on the board from 2008 to 2017.

In coming to the Libra Foundation, Hayling saw an opportunity to re-envision what a foundation can be. The foundation drastically simplified its application process and reduced burdensome reporting requirements for grantees, all of whom receive general operating support. In surveys, Libra grantees said the changes allowed them to focus even more energy on their work.

In a field that often talks about change, Hayling offered a blueprint, says Angie Chen, Libra’s former chief program officer, who now leads the Skyline Foundation. “She really created a model for the field of what it looks like to truly be in relationship with grantee partners, what it looks like to truly do trust-based philanthropy from the board on down.”

The changes she made at Libra to put more trust in the instincts and experiences of grantees also helped spur other grant makers to action. Ross, with the California Endowment, said leaders at his foundation had been thinking about how to bring more trust-based practices to their own work. “Once I heard that Crystal and the Libra Foundation were already on their way there, that gave me confidence,” he says. “She was at least a step or two ahead of the pack on trust-based philanthropy.”

More progressive grant makers are exploring ways to give grantees increased control over their funding — or at least paying lip service to trust-based giving practices. But top-down approaches guided by foundation leaders and expert consultants still reign supreme at institutions like the Rockefeller Foundation. Debates about donor power and grantee agency continue to roil the nonprofit world, from higher education down to grassroots nonprofits.

Implementing Trust-Based Philanthropy

The Libra Foundation was started in 2002 by members of the Pritzker family, who built their fortune through the Hyatt hotel chain and holdings in such companies as Braniff International Airways, Royal Caribbean Cruises, and Ticketmaster. When Hayling joined the staff in the summer of 2017, the foundation was in a moment of transition, having recently relocated from Chicago to San Francisco.

It was also in the process of moving from a fund led by the family and consultants to one led by staff.

“She had exactly what we needed, not only to see what was happening and to respond to it, but to also bring us as a family and as a board along with her in her vision,” says Susan Pritzker, board co-president at the Libra Foundation.

That involved learning some new language and new ways of being, Pritzker says, adding that Hayling “was a perfect teacher of those things.”

Hayling brought to Libra a firm faith in the power of movements and supporting community activists. The foundation funds groups working across intersecting issues of community safety, gender, and environmental and climate justice. Hayling convinced Libra’s trustees to double annual grant making to $50 million in advance of the 2020 election, a decision that proved prescient when the pandemic hit and calls for racial justice filled the streets in the wake of George Floyd’s murder by a police officer.

Democracy Frontlines Fund

During her time in Los Angeles, when Rodney King was beaten and large parts of South L.A. burned, Hayling saw how philanthropy rushed in and then retreated. She says those patterns of the ebb and flow of funding for racial justice have continued.

In 2020, she says, “I wanted to not have that one-year boom and then immediately go away.”

When she founded the Democracy Frontlines Fund with its initial three-year $36 million commitment, she saw it as an opportunity to change practice over time, going beyond the additional one-time support to racial justice or Black-led organizing that other foundations pledged.

A dozen grant makers, most of them family foundations like Libra, each initially pledged $3 million in general operating support for a minimum of three years and agreed to give up control over how that money would be spent. Money went to a slate of 11 Black-led intermediaries, including Black Voters Matter and the Communities Transforming Policing Fund, which distributed the funds to Black-led community organizations serving Black people. The donors are also participating in training sessions to dig deeper into how they can be better partners to movement leaders.

Hayling hears from many of Libra’s grantees that nonprofits are starting to see their dollars dry up. As some foundations move their racial-equity work into all their program areas, there’s no clear champion or voice within the organizations, she says. But the Democracy Frontline Fund donors — a group that has expanded to 14 grant makers — recently committed $37.5 million for an additional three years through 2026.

Democracy Frontlines Fund

Hayling will continue to serve as an adviser to the Fund after stepping down from Libra.

As she prepares to retire, Hayling says she believes the country and U.S. democracy is on a precipice. In a field that can be polite at the expense of being direct, she offers this encouragement for the next generation of leaders: “Step up, be bold, and be the people that we want to be remembered for being in the great arc of history.”

Reporting for this article was underwritten by a Lilly Endowment grant to enhance public understanding of philanthropy. The Chronicle is solely responsible for the content. See more about the Chronicle, the grant, how our foundation-supported journalism works, and our gift-acceptance policy.