These Funders are Redefining Sustainable Grantmaking
The Sustainable Grantmaking Benchmark helps foundations move beyond traditional practices by asking: is your grantmaking flexible, long-term and innovative enough to drive system change, critical to racial justice grantees?
In this issue, three leaders reflect on how the Sustainable Grantmaking Benchmark resonates with their work and how they’re already putting its principles into practice.
Tomeka Hart Wigginton is the CEO of United Way of the Mid-South and a Schott Foundation Trustee. Michelle Morales is the President of the Woods Fund Chicago. Michelle Larkin is the Vice President, Program Management at Robert Wood Johnson Foundation.
These leaders show that the path to sustainable grantmaking isn’t a one-size-fits-all. Their experiences reveal practical steps funders can take and how to navigate cultural and institutional challenges along the way.
Philos: Tell us a little about yourself and your organization.
Tomeka Hart Wigginton: Since December 2024, I’ve served as President and CEO of United Way of the Mid-South, based in Memphis, Tennessee. We serve eight counties across Tennessee, Mississippi, and Arkansas. Our mission is to address poverty through scalable, community-rooted initiatives. I came to United Way because I see it as a public philanthropy with the infrastructure to drive population-level impact, if we strengthen the nonprofit ecosystem through flexible and sustainable funding.
Michelle Morales: I’m Michelle Morales, and I’ve been President of Woods Fund Chicago for six years. Before taking on this role, I spent my career in youth development and alternative education, and I also served as a volunteer organizer. Honestly, I didn’t know you could get paid to organize until I joined the Woods Fund! That experience shaped how I lead today because I know firsthand the challenges nonprofits face. Woods Fund is a privately endowed, place-based foundation with a corpus of about $60 million. Since our incorporation in 1993, we’ve focused on community-based organizing and public policy advocacy in Chicago and nearby suburbs.
Michelle Larkin: I’m Michelle Larkin, Vice President of Program Management at the Robert Wood Johnson Foundation (RWJF), where I’ve worked for over 26 years. Throughout my career, I’ve leveraged my experience and expertise as a nurse and attorney to center equity in practice and policy. At RWJF, we take bold leaps to transform health in our lifetime and pave the way, together, to a future where health is no longer a privilege, but a right.
“Start with bronze, aim for silver—even if you're not ready for gold. The Benchmark shows us how to move toward truly sustainable philanthropy, and that's powerful.”
Philos: What does Sustainable Grantmaking and the Benchmark in practice look like to you?
Tomeka Wigginton: The Benchmark is a nudge, not a stick. It’s aspirational but practical. Like Weight Watchers, it tracks streaks, encouraging progress without shame. I’ve seen too much “calling out” in philanthropy that doesn’t lead to change. This approach calls us in, showing what’s possible, and letting foundations choose their path—bronze, silver, gold—toward sustainable practices. It’s a way to say, “Look at what others are doing,” and inspire movement.
At United Way, I’m using the Benchmark to drive internal change. When I interviewed for this role, I was candid about the frustrations I had as a grantee. Annual applications, burdensome reporting, and lack of committed multi-year funding were barriers. We are transforming our approach, building a strategy to eventually shift toward unrestricted, multi-year grants where appropriate, reduce written reporting requirements, and incorporate more meaningful conversations.
I’ve set goals for our team to move from where we are to where we want to be. Change is hard, but I’m using the Benchmark to show what I mean when I talk about being easier on grantees. It’s not about boiling the ocean—it’s about taking the next step. Where we can, move organizations to unrestricted funding. Try three-year grants. Replace written reports with conversations. These are doable shifts.
Michelle Morales: Our sustainable grantmaking and embedding trust-based philanthropy started during Covid. Then, we also realized grant agreements are contracts, and even minimal requirements can create legal exposure. So, we shifted to gift letters. This aligns perfectly with trust-based philanthropy, making our process far more efficient. Payments go out faster, and we and our grantees aren’t stuck chasing signatures.
What’s surprising is how many myths exist in philanthropy. People think these agreements are legally required, but they’re not for privately endowed foundations. We confirmed this with our counsel and auditors. Removing that red tape has freed us to be more responsive and trust-centered.
We also utilize a three-year budget. Interestingly, the idea originated from our previous board treasurer, Kurt Summers, who previously served as Chicago’s city treasurer. He suggested that a three-year budget would provide transparency and lock in our commitment to grantees—without tying it to market performance. Many foundations make multi-year grants contingent on returns, but we decided to prioritize impact over returns.
That shift has been transformative. It allows us to plan ahead, move money faster, and reduce uncertainty for grantees. Today, 95% of our portfolio receives three-year grants. The only exceptions are organizations still building relationships with us.
We are also exploring other investments to strengthen the ecosystem. We’re looking at catalytic investments and operational support. For example, we hired a Black-led investment firm to help us analyze grantee budgets and identify major cost drivers like rent. If many organizations are spending heavily on rent, we want to explore investments in property ownership.
We’re also researching professional employer organizations (PEOs) that could offer benefits such as healthcare and retirement plans to grantees. These are practical steps to address sustainability and reduce turnover—because strong movements need strong organizations.
Michelle Larkin: Sustainable grantmaking is about listening and adapting. It’s about centering the grantee relationship and equity to determine how we can best support each other. Here’s what it looks like in practice for us at RWJF. We are examining how we can increase multi-year grants, deepen our relationships with partners, and use new tools to enhance a sustained approach.
We are working to center equity and our grantee relationships. That requires us to ask different questions, to listen closely to grantee guidance, and adapt our processes to meet their needs while advancing shared goals.
We use a variety of funding mechanisms, including general operating support (GOS), project grants, flexible funding, endowments, and program-related investments (PRIs). We often pair GOS or project grants with another type of funding to ensure organizations can thrive now and in the future. It’s all about matching the right tool—or combination of tools—to the strategy and the organization’s needs.
Internally, we’ve made several shifts. We’ve challenged ourselves by asking: are we perpetuating the starvation cycle by spreading ourselves too thin? How are we supporting the grantee beyond the check? We’ve empowered staff to make longer, larger grants, and we’ve created equity rubrics to guide those decisions – Who benefits? Who doesn’t? How are the communities most impacted engaged? We’ve also standardized a 30% indirect rate for most organizations (excluding universities and healthcare institutions) to ensure that we are covering the true costs of working with us for our grantee partners.
The Benchmark is a good first step, and I’m hopeful that it will evolve to capture insights into how and where we can increase the equitable flow of resources, build trust and shift power to community. It’s all about how we support our grantee partners and improve our philanthropic practice.
“Sustainable grantmaking isn't just good for grantees—it makes foundations more effective.”
Philos: How can foundations ensure that Sustainable Grantmaking remains grounded in the needs and voices of the grantees and the communities they serve?
Tomeka Wigginton: Foundations must ground their grantmaking in community needs. That means listening, learning, and trusting. At Gates, I moved from compliance to relationship. I asked grantees what brought them joy, what kept them up at night, and how I could help. That built trust. When grantees feel safe, they share real challenges—and that’s when we can truly support them.
We must also rethink how we measure impact. Meetings aren’t metrics. Results are. I challenged grantees to promise less and deliver more. I asked for three-page proposals that focused on the problem, their solution, and the impact. It’s about clarity and trust, not bureaucracy.
Michelle Morales: Organizing and movement building are the least funded and most “risky” areas for philanthropy, especially direct-action organizing. But these are the strategies that create systemic change.
We’re issue-agnostic; our focus is on strengthening the organizing ecosystem. That means asking: What does the ecosystem need to thrive? Sometimes it’s money, but often it’s operational support, legal counsel, or crisis communications. We lend our own consultants and staff expertise to grantees because their survival matters.
After the murder of George Floyd, money poured into organizing—but as usual, it pulled back. That’s devastating because base-building requires consistent investment, not just election-season funding. Communities know when you only show up for a campaign. Sustainable grantmaking—multi-year, flexible funding—is what allows organizers to build trust and power over time. Without it, we’re stuck in cycles of reaction instead of transformation.
Michelle Larkin: At RWJF, we are dedicated to advancing systems-level change, which inherently requires long-term investment. We’ve always believed that relationships are critical to success, but we haven’t always been the best listeners. Over the years, we’ve shifted from a compliance orientation to one that centers relationships and shared strategy.
We ask ourselves: who has benefited from our funding, and who hasn’t? That reflection helps us make better choices and deepen our equity lens, listening to community, and shifting funds to the communities we seek to serve. Deeper relationships with grantee partners allow us to show up beyond the check—offering technical assistance, making connections, amplifying voices, and working together to create a future where health is no longer a privilege, but a right.
You can. What's getting in your way?
Philos: What advice would you give to other funders/trustees interested in sustainable grantmaking but aren’t sure about adopting it or where to start?
Tomeka Wigginton: As a trustee, I believe we play a significant role in shaping the culture and values of philanthropic organizations. Trustees don’t implement strategy, but we influence it. At the Schott Foundation, we’ve committed to sustainable grantmaking—longer-term investments, flexible dollars, capacity building, and reducing burdens on grantees. I’m proud that Schott participated in the Sustainable Grantmaking Benchmark report. It’s powerful when funders hold themselves to the same standards they expect of grantees. That’s real power-sharing.
As a CEO who wants to champion sustainable grantmaking, I say: listen to your grantees. Understand what is hindering them. Ask how you can make it easier for them to succeed. Challenge your foundation’s practices. Why do we require people to reapply every year? Why are we overburdening them with reports? Our job is to get money out the door and support impact. Let’s not make that harder than it needs to be.
I’m proud to be part of this movement. Consider me a champion. Let’s not let this report sit on a shelf. Let’s use it to build trust, shift power, and drive lasting change.
Michelle Morales: Unrestricted funding frees organizations to use resources where they’re needed most. As a former nonprofit leader, I know the pain of piecing together restricted dollars. At Woods Fund, we’ve eliminated applications and reports. Instead, we require one annual check-in meeting, and our program officers document the conversation. That’s our report. It fosters trust and enables everyone to focus on making an impact.
Ultimately, sustainable grantmaking isn’t just good for grantees—it makes foundations more effective. It lets us move money faster, respond to crises, and spend time on what matters: supporting organizations, amplifying their voices, and building power for systemic change.
Michelle Larkin: Interrogate why you’re hesitant. If it’s about control or compliance, ask whether that’s truly serving your mission. Multi-year funding reduces burden—for grantees and staff—and allows for deeper relationships and more meaningful impact. Systems change doesn’t happen in 12 months. You can still be a good steward of resources while trusting your partners. Ask them how they want the grant to be structured. Listen. Be flexible.
And remember, not everything is a nail—general operating support isn’t always the right tool. Use the tool or tools that best supports the work.
For more information on the Sustainable Grantmaking Benchmark, learn how to benchmark your organization, and find out which philanthropies have been benchmarked: