It’s all about striking a balance— and for gymnast Jordan Chiles, that’s sometimes literal. The two-time Olympian has brought sass, precision, and undeniable athleticism to every aspect of her incredible journey. From the taking on vaults to producing viral media moments, Chiles has been *that girl* and more.
As a new judge for the 31st Annual Webby Awards, we spoke with Chiles about what winning content looks like, how the best stories stand out, and the exciting opportunities for athletes looking to go from the floor to the feed.
Tell us a bit about your path as an athlete, and what’s been motivating you recently.
Gymnastics was my first love. I loved the energy, the challenge, and being able to do things others couldn’t. That journey took me to the Olympics twice and UCLA— some of the biggest stages in the world, but it also opened doors into fashion, content, and storytelling. People started getting to know me outside of the leotard, and I love that.
What keeps me excited is knowing I can keep growing. I can be an athlete, be creative, support the next generation, and explore things I haven’t done before. I’ve always said I’m more than my sport and getting to show people what that means has been such a special part of my journey.
This year’s Webby Talks theme, “By Popular Demand,” looks at the difference between work that captures attention and work that earns it, especially now that AI makes it easier than ever to optimize toward what’s already popular. In your industry, what does that trap look like in practice, and how do you spot work that’s chasing a formula versus work that’s genuinely breaking through?
In sports and brand content, that trap can look like deciding what an athlete’s story should be before you actually get to know them. There’s the big win, the emotional moment, the motivational quote. Those things can be powerful, but you can feel when someone is just checking boxes.
For me, the question is: Could you put any other athlete in this and have it feel exactly the same? If the answer is yes, we probably haven’t gone deep enough. The work that breaks through gives someone room to be themselves. Let me bring my humor, my style, my perspective. Sometimes the thing that connects most is the part you couldn’t have scripted.
With infinite iterations of content through AI, standing out – and creating something people remember, not just see – has never been harder. What do you look for to identify real cultural resonance versus something that’s just well-optimized to perform?
I pay attention to what people do after they watch. Are they sharing their own experiences? Sending it to someone because it says something they couldn’t find the words for? Bringing it up again after that first moment has passed? A lot of views can tell you something caught people’s attention. I want to know what stayed with them.
With athletes, people might come for the performance, but there’s an opportunity to connect through everything around it: confidence, pressure, identity, joy. When people see themselves in your story, or it helps them understand someone else a little better, that means something to me. Honestly I struggle with the pace of sharing because I’d rather share what’s impactful.
What’s your criteria for evaluating breakthrough work? What specific elements will make you think ‘this deserves a Webby Award?
I want to feel a clear point of view. Who made this, what are they trying to say, and why was this the right way to say it? Then I’m looking at the execution. The visuals, the storytelling, the sound, the way you experience it online. Do those choices actually make the idea stronger? You can have an amazing message, but how you bring people into it matters.
I also love work that takes a chance and trusts the audience. Something funny can deserve that recognition just as much as something emotional. If it surprises me, feels intentional, and gives me a reason to remember it, I’m paying attention.
How do you identify work that’s ahead of the curve? What signals in a project tell you ‘this is what the future looks like’ versus ‘this is just catching up to the present?
I look for work that makes me think, “Why haven’t we been doing this?” Especially when it gives people more ways to participate or brings in voices that haven’t had enough space.
In sports, that might mean letting fans experience more of an athlete’s world, or giving athletes more ownership of how their stories are told. There’s so much personality and creativity there that we’re still discovering. New technology gets my attention when it makes an experience better. I want to understand what it allows someone to do, feel, or access that they couldn’t before. That’s what makes me excited about where something could go next.
What are the biggest challenges facing creative in your industry today? What strategies are key to navigating these, and making work that has an impact?
One of the biggest challenges is the pressure to constantly produce. There’s always another post, another trend, another moment you’re supposed to jump on. As an athlete, you’re balancing that with training, competing, and actually living the life you’re sharing. For me, it helps to stay grounded in who I am and work with people who respect that. Have the conversation before the cameras come out. Ask what matters to the person whose story you’re telling. Give them room to contribute.
This interview has been edited for clarity.
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