Williams has helped steer The Rep through uncertain times, gaining victories in its successful Rally for The Rep campaign and in its search for new leadership—artistic director Kate Bergstrom was hired in 2024. Now four years into his tenure, Williams is both a familiar face and a trusted collaborator. “I’ve been fortunate to build a strong network of colleagues in different sectors of our community,” he says. “Although we have diverse backgrounds and areas of expertise, great things happen when we collaborate to address immediate and long-term challenges.”
2026 QUESTIONNAIRE
What advice would you give to the next generation of St. Louis entrepreneurs or leaders? Build your network and lean into collaboration. Since I arrived in St. Louis four years ago, I’ve been fortunate to build a strong network of colleagues in different sectors of our community. Although we have diverse backgrounds and areas of expertise, great things happen when we collaborate to address immediate and long-term challenges. Looking ahead, that collaboration and network building will need to continue to grow our collective impact in and out of our region.
What’s a risk you took in business that didn’t pan out—but taught you something valuable? Over the years, The Rep has piloted producing work in other parts of St. Louis, including Grand Center, Kirkwood, and the Delmar Loop. The concept had many strategic goals: expand programming outside of our home in Webster Groves and leverage facilities offering different space configurations and patron amenities. For many reasons, these endeavors have yet to be financially sustainable and for the moment, we are focusing our programming at our longtime home, the Loretto-Hilton Center. Each time, we learned valuable lessons like the power of innovation and how to think creatively about access and community.
What do you do when you’re feeling stuck or uninspired? When I feel stuck or uninspired, it’s a big sign for me to shift gears somehow. It could be a walk in Forest Park, wandering the Saint Louis Art Museum, or revisiting work by some of my favorite creators, such as Stephen Sondheim, Jim Henson, and Beyoncé. I know what you are thinking: That seems like a random list of artists, but for me, their breadth of work shares a common theme—what happens when heart meets craft. I come back to that concept to propel me forward, and it hasn’t let me down yet.
Who in your company (or industry) deserves more recognition for their impact? Leading our exceptional production staff is director of production Jayson M. Lawshee. With deep experience, an unshakable dedication to excellence, and a collaborative spirit that lifts every department, Jayson ensures every production not only runs smoothly but shines. His leadership turns ideas into reality, supporting designers and technicians in creating the unforgettable theatre our audiences love. Jayson is also a mega-talented lighting designer, with his work featured at The Rep, COCA, New Jewish Theatre, The Black Rep, and other venues throughout St. Louis.
What’s a local organization, nonprofit, or initiative that more people should know about—and why? One organization that I deeply admire is Prison Performing Arts (PPA). Because of the transformative power of storytelling and self-expression, the work they do in correctional facilities across St. Louis helps individuals rediscover their voice and their potential. Founded by Agnes Wilcox and currently led by Rachel Tibbets and John Wolbers, PPA opens doors to growth and rehabilitation—reminding us all that everyone deserves the chance to be seen, heard, and valued.
2025 QUESTIONNAIRE
PROFESSIONAL ACCOMPLISHMENTS & OPPORTUNITIES
What has you most excited about the future of your company or industry? As we look ahead, I’m incredibly excited about the possibilities for The Rep. The success of the Rally campaign reinforced just how deeply people believe in our mission and our place in the St. Louis arts landscape. At The Rep, we’re not just creating exceptional theater in St. Louis—we’re reimagining what a regional theater can be: a vibrant, inclusive space for creativity, dialogue, and connection. The future feels exciting, and we can’t wait to share it with our audiences!
If you could change one thing about your industry, what would it be and why? If I could change one thing about our industry, it would be the common perception that live theater always competes with streaming services or other on-demand entertainment. Theater offers something unique that can’t be replicated on a screen: an unfiltered, one-time-only experience that brings people together in real time. When audiences attend a live performance, they are part of a shared moment with an energy that’s truly irreplaceable. I’d love to see our field recognized not as an alternative to digital entertainment, but as an essential, immersive art form with its own magic and transformative power.
What’s the toughest business challenge you’ve had to overcome (excluding the pandemic) and why? One of the toughest business challenges we’ve faced is balancing the need for financial sustainability with our commitment to bold, adventurous programming. As a nonprofit arts organization, it’s essential to attract new audiences, foster innovation, and stay true to our mission‚ while making responsible financial decisions. Striking that balance isn’t easy, but I believe that taking these calculated risks is what keeps us relevant, inspiring, and impactful. It’s a challenge that requires vision, community support, and a lot of dedication, but the rewards—seeing our audiences moved, engaged, and growing—make it worth every bit of effort.
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MENTORS & PEERS
To whom or where do you go for sound business advice? I rely heavily on my team at The Rep, many of which are experts in their fields and contribute to how we steer the operations and strategic vision of the organization. I also have a dedicated and committed Board of Directors who are well established and experienced in industries across the metro. Last but certainly not least, I have strong relationships with the other arts leaders here in St. Louis — at other theatres, museums and cultural centers in the city and the county. We rely on each other for collaboration, conversation and innovation as we advance our sector forward to continued success.
Do you have a business mentor? If so, who and why? Patrick Willingham, Executive Director of The Public Theater in NY. He was my boss for over a decade and taught me how to strategically and tactically lead while maintaining a collaborative environment. Together, we were able to grow The Public over time and improve our business operations and infrastructure, complementing and supporting celebrated theatre onstage. He taught me how to trust your team, anticipate challenges and create opportunities for the business to thrive.
What piece of advice has had the most significant impact on your career? I performed improv in college and in New York City. One of the main tenets of improv is “Yes, and…” In improv, it encourages you to accept what your scene partner(s) have establish and expand on that line of thinking. In my career, I have used it to foster effective communication, stronger teamwork and an openness to ideas — qualities that have proven invaluable in my day to day life.
If you could have dinner with any two area business leaders, who would you choose and why? I’ve been very fortunate to share many a meal with the great business leaders in St. Louis. It’s hard to pick just two, but I will share that I deeply admire the work of Ken Kranzberg (and his wonderful wife, Nancy) for their transformation work in Grand Center. Penny Pennington is another name that comes to mind. What she has done at Edward Jones and in giving back to the arts community is truly remarkable.
Who is the most interesting under-the-radar/emerging business leader in St. Louis and why? I have to give a shout out to a dear friend and colleague, Charmian Aaron — who is Vice President of Engagement at Greater St. Louis, Inc. She is doing amazing work to engage with communities and businesses as we work towards a thriving metro region. She also loves theatre, which is always a plus!
What is one thing you would change about the St. Louis metro area business environment and why? It’s not a change per se, but I admire the work of Greater St. Louis Inc. My hope is that as civic and business leaders, we continue to support their many initiatives to expand inclusive economic growth in the region, including a focus on downtown St. Louis as a major center for opportunity and business attraction.
BACKGROUND
Where were you born? I was born on Long Island, NY, about an hour from Manhattan.
What was your childhood aspiration? For many years growing up, I wanted to play second base for the New York Yankees. That’s before I tried my hand at acting, which led me to aspirations of being a famous actor. The business side of theatre came as a surprise to me once I learned that all of the magic onstage has a team of savvy and creative folks offstage adding to experience.
What was your first job, and what did you learn from it? My very first job was as a photographer assistant for weddings. I learned a lot about photography, how focusing on others can lead to improved well-being, improved performance, and a greater sense of purpose. And that regularly wearing a polyester tuxedo in the middle of summer is not ideal.
What educational degrees do you hold, and where were they earned? I have degrees in Theatre and Marketing from Fairfield University in Fairfield, CT. I also studied at Regents University in London, where I merged my business acumen for my love of theatre.
HOBBIES & INTERESTS
If you were not in your current profession, what would you be doing and why? I would love to run a restaurant that’s both a local hang out and a destination for good food and amazing service. There’s something about the energy, the atmosphere and the experience of a lively restaurant that really appeals to me. I love to work hard and I love to entertain and interact with the many wonderful community members here in St. Louis.
What is your favorite St. Louis-area restaurant, and what do you typically order there? We have so many amazing restaurants here in St. Louis, it’s hard to pick just one, so here are three dishes at three of my favorite places to eat: the Isaan Hamachi at Sado, the Roast Chicken at Louie, and the Samoa at Sydney Street Café.
What is one item you recently crossed off your bucket list? I’ve been to three of the four tennis grand slams: Wimbledon, Roland Garros, and The US Open. I’m planning to travel to Melbourne for the Australian Open in the next few years.
What is one book you think everyone should read (or podcast everyone should listen to) and why? I am very big on organizational culture and communication. I’ve recommended Crucial Conversations: Tools for Talking When the Stakes Are High by Kerry Patterson to almost everyone who will listen. At all ages, and in many aspects of our lives, communication is key. I’ve seen the lessons in this book unlock collaboration and confidence in many colleagues over the years.
What’s your hobby/passion? I am a huge tennis fan. I follow both the men’s and women’s tours and make annual trips to as many tournaments as I can.
What is your most prized possession? I have a collection of programs and ticket stubs from every movie, concert, play and sporting event I have attended. It’s a collection over 30 years in the making, and each one celebrates a unique moment in my life, mostly shared with loved ones and close friends.
What would people be surprised to learn about you—a fun fact? I once shared the stage with legendary actor Paul Newman in a production of Our Town at The Westport Country Playhouse over 20 years ago.
What is your go-to karaoke song? “Believe” by Cher. It’s a fun song and most people know the words, so it becomes a group sing-a-long very quickly—but what can I say? I’m a great collaborator!
