Board Member Spotlight: Richard Stephens

A Strategic Heart for Impact 

Few individuals blend professional accomplishment with heartfelt philanthropy quite like Richard “Rich” Stephens, current Board Chair of the Unbridled Charitable Foundation (UCF). With more than three decades of experience in the insurance and employee benefits space and an unwavering commitment to children’s causes, Rich plays a pivotal role in shaping the foundation’s vision, voice, and value. 

A Fortuitous Introduction That Shaped a Model 

Rich’s story with Unbridled began serendipitously, but its impact would ripple far beyond that initial connection. At an early Unbridled Eve Gala, Rich was introduced to Blessings in a Backpack, a nonprofit dedicated to feeding food-insecure children over weekends. That introduction wasn’t just meaningful, it was catalytic. 

Moved by the mission and impressed by the organization’s leadership, Rich quickly deepened his involvement, ultimately becoming Chairman of the National Board. Under his stewardship, Blessings significantly expanded its reach, delivering over 1 million hunger-free weekends to children nationwide. 

For Unbridled, this was more than a philanthropic success, it became a prototype. The model of connecting high-impact individuals with aligned causes through unforgettable events has since become core to how UCF builds partnerships and pursues its mission. 

A Career of Leadership, Clarity, and Connection 

Professionally, Rich has helped shape the modern benefits industry. Today, he serves as the U.S. Health & Benefits Chief Broking Officer at Aon, guiding client strategy across a national platform. His earlier leadership roles at industry giants like Cigna, Marsh, and Willis gave him a deep well of experience in creating distribution systems, nurturing client relationships, and simplifying complexity in a notoriously layered industry. 

If there’s one thing he’d change? Rich would eliminate the overwhelming complexity in healthcare delivery systems, a challenge he’s been chipping away at throughout his career. 

His career is also marked by his belief in storytelling as a leadership tool. “If you can’t tell a story that is meaningful and drives toward an outcome,” he once said, “you’re wasting time.” That mindset infuses his role at UCF, where he helps sponsors, donors, and beneficiaries see themselves in the larger narrative of lasting impact. 

Wisdom, Humor, and the Heart of a Mentor 

Rich isn’t just a strategist; he’s a natural mentor. As he describes it, part of the joy of longevity in business is the ability to pass on knowledge and elevate those just entering the field. A self-proclaimed comedy fan with a dream of being on stage, he credits Robin Williams as one of his personal heroes. He values Williams’ mastery of seemingly spontaneous brilliance, underpinned by deliberate preparation. 

That humor doesn’t go unnoticed at home. “Fifteen years ago, I was hilarious,” he laughs, “Now I’m just embarrassing.” The proud father of twins and a third child, Rich speaks candidly about the challenge of raising independent spirits—and the joy of family adventures, including driving to 47 of the 48 continental states as a child with his own parents. 

His other hero? Walt Disney, a figure he admires for turning big, bold visions into reality. “He understood the value of good storytelling, which we’ve now all brought into our lives and business.” 

Living the Unbridled Vision 

At UCF, Rich is a key architect in helping us grow with purpose. He brings clarity to our sponsorship approach, helps refine our organizational strategy, and ensures that our partnerships, like the one with Blessings in a Backpack, are built for depth, not just duration. 

He exemplifies what Unbridled is all about: making memorable connections that transform lives. Whether it’s connecting a donor with a mission, a company with a cause, or an organization with a leader, it’s all about impact that lasts. 

Thank You, Rich 

As we spotlight Rich Stephens, we honor a visionary board member and a deeply valued friend. His introduction to Blessings in a Backpack was more than a coincidence. It was the spark that helped us define a blueprint for meaningful, sustainable giving. 

Thank you, Rich, for your leadership, your stories, and your unwavering heart. You’re helping all of us live and give Unbridled. 

Recent Articles

• 2 weeks ago

Sponsor Spotlight: The Galt House Hotel

Since 2012, the Unbridled Eve Derby Gala has taken place at the Galt House Hotel, Louisville’s only hotel on the Ohio River and one of the city’s most iconic landmarks. What began as a client-vendor arrangement has developed into a...

Article • 2 min read

• 2 weeks ago

From Velvet Cushions to Velvet Grit: The Unbreakable Journey of Dr. Laverne Cox

Dr. LaVerne Cox is a fervent Unbridled supporter and has been there since the beginning.  LaVerne has been overseeing Unbridled’s VIP gift bags for years and embodies what Unbridled is about.  Laverne’s life reads like a novel you can't put...

Article • 3 min read

• 2 weeks ago

Churchill Mae: Tammy York Day’s Next Bold Chapter

After a distinguished career spanning more than two decades, Tammy York-Day has launched a new venture that blends her deep philanthropic roots with her unparalleled eye for elegance and style. Best known for her leadership at Delta Dental of Kentucky...

Article • 2 min read

• 2 weeks ago

The Big News: A Historic Shift for the 2026 Running of the Oaks, and a Bold New Chapter for Unbridled Eve

If you haven’t yet heard, a major change is coming to one of Louisville’s most beloved traditions. Churchill Downs has officially announced that the 2026 Longines Kentucky Oaks will be run at 8:40 PM, marking a significant shift from the...

Article • 3 min read