Disclaimer: The views and opinions expressed by the guest speaker in this episode are their own and do not necessarily reflect the official policy or position of any organization they may be affiliated with.
Philanthropy, at its core, is about uplifting communities and supporting societal progress. But for many communities, especially those historically underfunded and excluded, philanthropy is distant—another system weighted by power dynamics and inequities. That’s where voices like Roland Kennedy Jr. come in, calling for a shift in how we approach equity within the sector.
In a recent episode of the Untapped Philanthropy podcast, we sit down with Roland Kennedy Jr., Grants Director at the Carnegie Corporation and board member of PEAK Grantmaking and Barbershop Books. Through his career, Kennedy has championed a new vision for philanthropy—one that centers on the communities it serves, builds trust, and dismantles longstanding barriers.
Here are some of the most impactful takeaways from their conversation.
Roland Kennedy Jr. has spent a decade in philanthropy, but his roots in North Philadelphia have always guided his approach. His upbringing in a community focused on organizing and activism shaped how he views the relationship between philanthropy and equity. “I grew up in a community talking about what the needs are of your neighbors, how you impact a network in terms of those that really need food or paying the bills or dinner table conversations focused on what is really good for your city,” Kennedy shares. It’s these personal experiences that inform his work as a leader today.
Kennedy’s journey into philanthropy wasn’t traditional. After starting his career in government, he found himself applying for a corporate foundation role. Although he didn’t get that job, it opened a new door for him. Reflecting on that pivotal moment, he notes, “I applied for the job, did not get it, but got a call back about two to three weeks later for another role as an analyst that I did get... I didn’t realize that that was a good jumping off point for opportunities that I didn’t even have an imagination for in terms of informing what my future would look like in this work.” Since then, he has leveraged his background in policy and governance to drive impactful change in philanthropy, always keeping the needs of marginalized communities in focus.
For Kennedy, equity isn’t just a trendy term—it’s the foundation of his work. Throughout his career, he has strived to redirect philanthropic capital to communities that historically have received less support. “I don’t say charity, I don’t use that word as much because the more I’ve learned about this work, it really is a capital structure,” he explains. This distinction is important because it reframes how funders should think about their work—not as handouts, but as investments in the future of underserved communities.
Kennedy emphasizes that true equity in philanthropy means addressing who gets funded, why they get funded, and how. It’s about not just acknowledging the barriers that exist but actively working to remove them. He points out that less than 5% of Black leaders are represented in philanthropy and even fewer in grant management roles. “I represent less than 5% of Black leaders in philanthropy and even less than 1% of Black leaders in the grant management side of philanthropy,” Kennedy explains.
This personal connection to equity motivates Kennedy to push for changes that ensure more voices are heard, particularly those from the communities philanthropy aims to serve. And this requires intentionality. “Philanthropy often operates in a space of privilege... but we need to recognize the unequal power dynamics and work to change that.”
In discussing the complexities of equity, Kennedy stresses the importance of trust. For many marginalized communities, particularly Black and Hispanic communities, trust in philanthropic institutions is low. This stems from a history of exclusion and a lack of representation in decision-making processes. Kennedy emphasizes that philanthropy must work harder to build trust by showing it through actions, not just words.
One of the key barriers Kennedy highlights is the uneven playing field between funders and grantees. “We are not equal. When your organization has millions and billions of dollars and you’re going to nonprofits and communities that don’t. That is not equal. That’s not even equitable.” He believes philanthropy must start by acknowledging this imbalance and working to create more genuine partnerships.
Building trust isn’t easy, and Kennedy is clear that it goes beyond surface-level gestures. It requires funders to shift how they think about their role in the process. By recognizing the power dynamics at play, funders can begin to engage more equitably with grantees, centering community voices in their decision-making processes.
In today’s digital world, technology can either reinforce existing barriers or help dismantle them. Kennedy sees tremendous potential in leveraging technology—especially grant management systems (GMS)—to promote equity. However, he also points out that tech companies have largely been missing from the equity conversation. “Why have we not engaged GMS companies on conversations around equity? Why are they not at the table?” he asks, noting that despite processing billions in grants annually, these platforms aren’t always part of the discussions around diversity and equity.
Kennedy delivered a call to action during the PEAK Grantmaking conference, urging GMS companies like Fluxx to engage more deeply in equity conversations. “If you keep bringing the same people to the same table for the same conversations and expect a different outcome, that’s not likely to happen,” he explains. By incorporating technology platforms into these discussions, philanthropy can create systems that better reflect the needs of all communities.
At Fluxx, which processed $23 billion in grants last year, Kennedy’s words struck a chord. As organizations strive to make their processes more equitable, GMS companies have a critical role to play in ensuring capital flows equitably. Kennedy challenges both funders and technology providers to ask tough questions about their practices and to innovate toward more inclusive solutions.
Philanthropy often operates in its own bubble, but Kennedy is a strong advocate for learning from other sectors. During his career, he has sought insights from government, the private sector, and nonprofit organizations, recognizing that they often approach problems with a different sense of urgency. “There’s this narrative that there aren’t any emergencies in philanthropy,” he says, “but yet even some data points that I just shared with you all earlier, that there are a number of Black, Brown, and Native-led nonprofits that need resourcing... that sounds like an emergency to me.”
By engaging with sectors that are used to navigating urgent challenges, Kennedy brings new perspectives into philanthropy. He encourages other leaders to adopt this cross-sector mindset and seek out lessons that can help break the inertia in traditional philanthropic approaches.
As Roland Kennedy Jr. makes clear, philanthropy has a lot of work to do if it’s to live up to its mission of driving equity. He offers several concrete steps for moving the sector forward, including diversifying leadership in GMS companies, creating equity-focused fellowships, and adopting more flexible, community-driven funding models.
The future of philanthropy, according to Kennedy, is not just about words—it’s about taking real, tangible actions to dismantle the barriers that have kept marginalized communities on the sidelines for too long. By building trust, embracing equity, and harnessing technology, philanthropy can finally begin to realize its potential to create meaningful, lasting change.
The conversation with Roland Kennedy Jr. is a timely reminder of the importance of centering equity in everything we do. His insights challenge us to reflect on how we approach philanthropy, urging us to move beyond the status quo and push for a future where every community is seen, heard, and supported.
To learn more about Roland Kennedy Jr.'s work, visit Carnegie Corporation or explore the Black Voices in Grant Management journal.
For a comprehensive list of all Untapped Philanthropy episodes, visit the Fluxx blog, or your favorite podcast listening station, including Apple Podcasts and Spotify.
Download the transcript here.
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