Leadership and Legacy Underscore 5th Annual Women’s Summit

In June, the Kentucky Chamber’s 5th Annual Women’s Summit, presented by Fifth Third Bank, brought together more than 600 attendees to celebrate and learn from women shaping the Commonwealth, including the 2025 Woman in Leadership award honoree Diane Medley.

Kentucky Chamber President and CEO Ashli Watts said the Chamber is proud to convene women from diverse industries and backgrounds to share their experiences, insights, and strategies for success. 

“Our goal is to empower each other, celebrate our achievements, and work collaboratively to overcome the challenges we face in our professional and personal lives,” Watts said.

In a video message, Kentucky First Lady Britainy Beshear celebrated women’s leadership across the Commonwealth and emphasized the importance of lifting one another to build stronger communities and a better future for all Kentuckians.

As presenting sponsor, Kentucky Regional President of Fifth Third Bank and Kentucky Chamber Foundation Board Chair Kim Halbauer spoke on the company’s commitment to supporting women in business and leadership roles.

Opening Keynote: Lessons from Coaching Women’s Basketball

University of Kentucky Women’s Basketball Head Coach Kenny Brooks, the 2025 Sporting News National Coach of the Year, spoke on his personal journey and calling to coach women’s sports. Brooks spoke about his responsibility not only to win games but to shape and empower young women.

Brooks emphasized the importance of building a culture that focuses on character, sacrifice, and support. With deep appreciation for the fan base, administration, and his own family, Brooks said he uses his role to help women lead, thrive, and inspire.

“I don’t want to be anywhere that can’t empower women. And it’s my calling to give these wonderful young women who got an opportunity to go out and run our country, run our world. Because I think it would be a better place with more women in positions of power.”

Miss Kentucky and USA, Tara Conner

Miss Kentucky 2006, Miss USA 2006, and recovery advocate Tara Conner talked with Kim Halbauer about how she has turned her challenges into purpose. Reflecting on the pressures of her public image, Conner spoke candidly about her experience with substance use disorder, which began at age 14, and the trauma she carried long before pageantry. After making headlines for failing a drug test in 2006, she said her most difficult moment became a turning point.

Conner said she uses her platform to advocate for recovery, share her personal journey, and remind others they are not alone. Now 18 years into her sobriety journey, she says her proudest title is mother, and her focus is on building a future based on honesty, service, and support.

“Healing is not linear. But it’s a lot easier when you say it out loud than trying to do it alone,” Conner said.

Jennifer Barber on Leadership, Legacy, and Lifting Others

Jennifer Barber, Louisville Partner in Charge at Frost Brown Todd LLP, shared how her upbringing as the daughter of Chinese immigrants shaped her approach to leadership. Raised in her family’s restaurant in Frankfort, Barber spoke about the courage, work ethic, and resilience instilled in her from an early age. These values laid the foundation for her career, ranging from law, diplomacy, and public service.

“As women, we have unique strengths that make us exceptional leaders. Our empathy, resilience, and collaborative skills are invaluable assets. So embrace it. With every step of my journey, I have been blessed to have great family, friends, mentors, and colleagues who believed in me, motivated and encouraged me,” she said.

Reflecting on moments of doubt early in her legal career, Barber said her turning point came when she began leading with authenticity. She emphasized the power of intentional mentorship, empathy, and lifting others while rising through the ranks.

“Make your legacy not just about what you achieved, but what you enabled others to achieve,” Barber told the audience. “Be the person in the room that adds value—or the one who listens and is open to experiences different from your own.”

A Conversation with Damaris Phillips

Kentucky native and celebrity chef Damaris Phillips joined Seema Sheth, Senior Vice President and Regional Executive at the Louisville Branch of the Federal Reserve Bank of St. Louis, to talk about her journey from culinary school to national television and highlight her passion for food, hospitality, and lifting up others.

Phillips reflected on the highs and lows of her career, including the cancellation of her Food Network show Southern at Heart. With the help of mentors like Guy Fieri and Bobby Flay, she has redefined her purpose by leaning into what makes her unique. “There’s not always going to be someone there to tell you to take the stage,” she learned. “Sometimes, you have to do it yourself.”

Woman in Leadership Award

Diane Medley, Principal and Managing Member of Waterfront Financial Group, was honored as the 2025 Woman in Leadership Award recipient for her decades of service, business excellence, and longstanding contributions to Kentucky’s economic landscape. In a conversation with Ashli Watts, Medley reflected on her journey from rural Kentucky to building Mountjoy Chilton Medley and serving as chair of the Kentucky Chamber Board of Directors in 2022.

Medley co-founded Chilton & Medley in 1988, which turned into MCM CPAs and Advisors in 2010. In the years after, MCM CPAs and Advisors grew through a series of mergers and acquisitions to become the largest CPA firm in the region. As the Managing Partner and Co-Founder, she was the first woman in the region to have this leadership position within a major firm, and one of only three in the U.S. Top 100 at that time.  In 2023, after the three named partners had retired from firm leadership, MCM was acquired by Cherry Bekaert LLP. In 2024, Diane and another partner launched Waterfront Financial Group, a firm specializing in comprehensive tax planning and advisory services for high-net-worth, professional, or entrepreneurial individuals with complex tax and accounting needs. 

Medley has made a significant impact on the University of Louisville as Chair of both the University Board of Trustees and the UofL Foundation, among many other civic and community leadership roles. She emphasized the importance of mentorship, community service, and empowering people to grow beyond what they believed possible.

“People want to follow an inspiration,” she said. “You have to find a way to inspire them to be better and do something wonderful.”

A Conversation with Women in Media

Journalists Kirby Adams, lifestyle reporter at the Louisville Courier-Journal; Sarah Ladd, health and policy reporter at the Kentucky Lantern; Amber Philpott, news anchor and reporter at WKYT News; and Kerri Richardson, president of C2 Strategic Communications, shared their experiences in local journalism and the evolving role of women in media. From covering major events like the COVID-19 pandemic and natural disasters to highlighting issues such as child care and Kentucky’s growing film industry, the panelists emphasized the importance of community storytelling in informing and connecting people across the state.

The journalists, representing diverse news sources, discussed the challenges of shrinking newsrooms, misinformation, and the rise of artificial intelligence. They also shared that women in the newsroom bring power through diverse voices and angles, empathetic reporting, and broader coverage. 

A Conversation with the Women of the Kentucky Supreme Court

For the first time in state history, women hold the majority of seats on Kentucky’s highest court. Kentucky Chamber Senior Vice President of Public Affairs Kate Shanks, Chief Justice Debra Hembree Lambert, Justices Angela McCormick Bisig, Pamela Goodwine, and Michelle Keller shared their personal journeys, insights from the bench, and the importance of broad perspectives in shaping Kentucky’s legal landscape.

The panel reflected on the importance of mentorship, resilience, and public service, especially for future lawyers and judges. They discussed overcoming early career barriers, navigating a male-dominated field, and the role of education and support systems in their success. Several emphasized their work to expand access to justice and address mental health challenges within the court system.

“I want to be the role models we didn’t have,” Justice Goodwine said.