close

Rev. Jen Bailey

Rev. Jen Bailey

This past August, in recognition of Black Philanthropy Month and the global call to honor the theme of Sankofa — a West African principle that urges us to “go back and get it” — we proudly welcomed the next class of Gamechangers: Black philanthropic leaders and bold collaborators shaping the future through innovation, generosity, and trust.


bailey-screenshot play_arrow
Rev. Jen Bailey


Rev. Jen Bailey is the executive director of the Dan and Margaret Maddox Fund and a nationally respected faith leader, writer, and advocate for justice. She carries forward a lineage of Black women who built communities through service, spiritual grounding, and quiet acts of generosity. Born into a family shaped by the Great Migration and raised among church mothers who could turn a simple meal into a feast for an entire neighborhood, she learned early that service to mankind is both a responsibility and a joy.

Jen’s work in philanthropy is rooted in that legacy. Whether guiding the Maddox Fund, preaching in her church community, or nurturing collaborative leadership across Middle Tennessee, she brings a steadfast commitment to youth, to the environment, and to the collective well-being of the region. She leads with clarity, radical joy, and a belief that every person carries wisdom worthy of honor.


Tell us your story. (Your journey, your work, or what brought you to where you are today.)

When I reflect on my journey into philanthropy, I always return to the definition of philanthropy as service to mankind. My understanding of service was shaped by my childhood in the Midwest, where I was raised by the second wave of the Great Migration and surrounded by church mothers who lived out generosity every day.

These women did not always have financial resources, but they embodied a spirit of giving that fed entire communities. I often say I knew the miracle of the loaves and fishes was real because I watched women like Sister Weldon and Sister Watson stretch spaghetti and dinner rolls into a meal for anyone who needed it. Their faith, resilience, and commitment to community are in my bones. They guide how I show up for Middle Tennessee and how I understand the responsibility of caring for others.

Name a person, tradition, or community value from your past that guides how you give or serve today.

A value that guides me is the practice of radical joy. We live in a world that often pulls our attention toward chaos, confusion, and pain. The women who raised me survived Jim and Jane Crow, survived deep personal trauma, and survived relationships and systems that were not designed for them to thrive. Yet they still celebrated. They held joy as a discipline, not an afterthought.

That practice taught me that joy is a principle that sustains hope. It is a form of resistance and a way to imagine a better future. I carry that value into every space I inhabit today.

Sankofa teaches us to look back so we can move forward. If you could speak to your younger self or to future generations of Black gamechangers, what lesson or moment from your past would you share?

If I imagine myself as a future church mother with a big hat, sitting on the front pew with hard candies in my purse, I would tell the next generation that it is okay to grow deep and wide instead of fast and long.

Many of us are taught to hustle, to climb quickly, and to carry the weight of lifting everyone with us. That pressure is real, but when we push forward without tending to our holistic well-being or staying connected to community, it leads to burnout and isolation.

To grow deep and wide means to invest in your people, to build collective strength, and to honor the fact that success is shared. It means trusting that when you step back, someone else will step in. That is how Black communities have survived for generations, and it is how we will continue to create justice and belonging.

The parable of the talents teaches us to grow and share what we’ve been given. How have you used your gifts — whether time, talent, or resources — to make an impact in your community?

I understand my gifts as something that did not begin with me. They are offerings entrusted to me by my ancestors and by spirit. Whether I am serving in my church on Sundays or leading at the Maddox Fund, those gifts only matter when they serve a larger purpose.

I am always learning, growing, and discovering new abilities. One of the greatest gifts I have received is the wisdom to know that we never reach the point where we know everything. There is always something to learn from what I call my senior saints and my playground prophets. Everyone has a lesson to offer if we are willing to receive it.

How have you seen Black generosity and community investment show up in ways that might not always be recognized as philanthropy?

When my mother passed in 2016 after a long battle with cancer, our community surrounded us. She spent her last months at home on hospice, and we never went hungry. People showed up with pans of food, with prayer, with blessing, with presence. That care held us together.

This kind of generosity is not often acknowledged in the same way that writing a large check is acknowledged. But to me, it is the foundation of true philanthropy. It is service rooted in love, community, and shared responsibility.

How do you define “being a Gamechanger” in collaborative efforts or philanthropy?

A gamechanger is someone who sees the world as it is and refuses to accept that it must stay that way. It is a person who aligns their values with action, whether the action is large or small. Gamechangers use imagination and conviction to move toward what can be, not just what is. They do the work with courage, with vision, and with commitment.

What wisdom or encouragement would you share with someone in Nashville who’s just beginning their journey here locally as a philanthropist or community leader?

Pay attention to those who came before you. Middle Tennessee is full of people with deep wisdom and lived experience. Their stories and lessons contain the knowledge needed to understand who we are as a community and what we can become.

Seeing yourself as part of an unfolding story is the foundation for any real transformation you want to create.

What are you curious about, excited to see unfold, and/or looking forward to initiating over the next year?

I am energized by the work happening at the Dan and Margaret Maddox Fund as we reimagine ourselves as a foundation for the future. Our commitments to youth and the environment feel especially urgent in a time when both areas of work face significant threats.

What gives me hope is the creativity and imagination of our partners. They are envisioning futures that break from harmful patterns of the past. They are planting seeds in what Mia Birdsong calls toxic soil, trusting that something new and beautiful can emerge. I am excited to witness what grows from that courage and that collective vision.

Black Philanthropy Month: Sankofa Now!

The past holds the key to our future. As we navigate growing challenges, we must draw strength from those who came before us. For this year’s Black Philanthropy Month recognition, we must:

  • Remember our philanthropic roots, built on collective care and community-driven investment. 
  • Reclaim our power to shape the future, ensuring Black-led change is not just recognized but sustained.
  • Rise by reinvesting in our people, our movements, and our solutions, because the future of Black philanthropy (and all humanity) depends on what we do today.

A thriving Black community benefits everyone. The fight for equity, opportunity, and justice strengthens our collective future, creating a world where all can prosper. Black philanthropy has always been a catalyst for change. In a time when progress is at risk, we need all hands on deck.

The greatness of a community is most accurately measured by the compassionate actions of its members.

Coretta Scott King
Community Foundation of Middle Tennessee Logo

This site uses cookies to offer you a better browsing experience. If you continue using our website, we'll assume that you are happy to receive all cookies on this website and you agree to our Privacy Policy.

close