Heart & Hustle: Continuing a Legacy of Stewardship and Servant Leadership
by Sarad Davenport | Photos by Rebecca George
Service isn’t just something Kimberly Sheffield does—it’s woven into her very DNA. Raised in rural Madison County, Virginia, Sheffield grew up steeped in a tradition of quiet, tireless community leadership. Her mother, a minister, modeled a profound level of selflessness, fostering between 20 and 25 children over the years and adopting several directly into their home. Meanwhile, her father provided the blueprint for her entrepreneurial grit, landing high-level commercial cleaning contracts decades ago that brought in unheard-of financial security for a Black family in the region at the time. “I was born and raised in the boonies,” Sheffield recalls with a laugh. “I come from a very religious background… community service and being a servant leader was something that I saw a lot of.”
Looking back at her upbringing, Sheffield recognizes the two pillars that shaped her path and gave her a clear direction early on. “I think I got the best of both of them while I got my heart from my mom, my grind came from my dad,” she reflects. Her father was the epitome of an entrepreneur, operating at a level that set a lasting example for what dedicated hard work could achieve. “My dad was doing big things 30, 40 years ago… this man could do anything and he didn’t do it low level, he did everything at a very high level.” Watching her parents navigate their respective callings taught her early on what it truly meant to show up for others. “I saw a lot of folks giving of their time, talent, and treasure, and yeah, so I think that it was inevitable for me to pick up the torch and be a servant leader in my own career.”
For 17 years, Sheffield channeled that inherited drive into corporate America as an insurance specialist. Her focus was deliberate: educating Black and Brown families on asset protection, homeownership, and building generational wealth. Yet, beneath that professional fulfillment lay a heavy emotional toll as she found herself battling vicarious trauma and anxiety at times while guiding families through grief, death claims, and unexpected loss. Sitting with a family after a sudden loss meant walking through the full cycle of grieving alongside them, and looking at countless death certificates made her realize how fragile life is. “I spent 17 years in the insurance industry and I was burnt out,” she admits. “My niche was Black and Brown folks and educating them on insurance… but I always wanted more, I always wanted to be more involved in the community.”
She needed a shift to clear her head and restore her well-being. What began as a short-term, six-month contract to help oversee administrative operations at the Jefferson School Foundation turned out to be a life-altering turning point. Stepping through those doors reignited a spark that corporate sales had slowly dimmed, reconnecting her to a deeper sense of community. “I think coming to Jefferson School saved my life in more ways than one because I was in a very dark place,” Sheffield shares. “I had forgotten what fueled me, and people and community is what fueled me—this place really reignited that fire in me.”
Today, as executive director of the foundation, Sheffield stands as one of the stewards of that historic legacy. This summer, the foundation marks a momentous century celebration for the 1926 building that houses the Jefferson School African American Heritage Center. The milestone is designed as a living bridge between historic memory and future generations, featuring an alumni reception where elders and descendants can reconnect over shared stories, followed by a community-wide Legacy Run, live performances from Hip-Hop scholar A.D. Carson, interactive art, and a time capsule project. “This place means a lot to a lot of people,” Sheffield explains. “I hear the stories and feel the stories and they make me want to work harder here in preserving this space because it’s not just a building.”
Her dedication to uplifting others doesn’t stop at the historic building’s doors. Through Kenley’s Mission—an organization named after her daughter—she quietly supports families navigating sudden economic crises through bill assistance, backpack drives, and holiday meals. She also coaches youth travel cheer as commissioner of the Pom Squad, leads local blood donation drives for sickle cell awareness with the American Red Cross, and chairs the Charlottesville Minority Business Alliance. “I currently serve as the commissioner and coach for Madison County Youth Cheerleading. I truly believe in elevating and activating the young people,” Sheffield says, summing up her broad approach to community work. “I’m an all-serving leader… here to serve.” Through every effort, she continues to honor the heart and hustle passed down to her, ensuring that space, resources, and legacy remain preserved for generations to come.
To RSVP for the Alumni Reception, please use the link below. Come be part of the history!
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