Picture this: An improv comic, an NHL player, and a Fortune 500 CEO waltz into a theater. No, it’s not the setup for a poorly written punchline; it’s just another day in the corporate comedy circus known as Second City Works.
Yes, the illustrious Chicago-based comedy giant has taken a detour from its usual hilarity. Instead of crafting comedic gold, they’ve decided to sprinkle some improv fairy dust on corporate executives and professional athletes to make them better at something far more terrifying than stand-up: communication.
Now, this isn’t a new cash grab. Second City Works has been around longer than most of us can remember, and with social media on the rise, everyone now expects corporate suits and sports stars to be social butterflies. In 2025, forgetting how to form a coherent tweet could land you in hot water—or worse, a TikTok dance challenge.
“We’re not teaching you to be funny,” says Tyler Kempf, the creative director expecting to be hilariously misunderstood. “We just kind of infer it from the giggles and the occasional Shrek-themed improv game. But really, we’re here to show you how the art of spontaneous silliness can save your corporate life.”
Second City Works is now a linchpin in the company’s empire, which is now fancied up and under the watchful eye of Strauss Zelnick’s private equity firm, ZMC. They’ve opened training facilities faster than you can say “mediocre improv night,” stretching from Chicago to New York and Toronto. Because yes, the world absolutely needed more improv.
Surprisingly, the pandemic didn’t kill the vibe; it merely prompted a shift in revenue streams. Instead of just selling tickets to live shows, they leaned into the ever-lucrative marketplace of corporate training—because who wouldn’t pay to be taught how to avoid the abyss of awkwardness in a Zoom meeting?
More than 80 “improv facilitators” now roam the U.S. and Canada, trained in the noble art of making business meetings a little less depressing. They’ve conducted over 650 events recently, polishing the communication skills of clients like Uber and the Chicago Cubs. It’s the corporate equivalent of a motivational speaker, but with fewer cheesy quotes and more spontaneous group games.
Kempf often opens sessions by asking, “How many of you are scared right now?” and, to no one’s surprise, hands shoot up faster than a cat meme goes viral. Improvising is naturally terrifying—especially when it’s tied to giving a presentation without PowerPoint’s comforting glow.
The cornerstone of their method? The legendary improv phrase “Yes, and…”, which Kempf assures us isn’t just an invite to agree awkwardly. It’s more like accepting the existential dread of your current job and then building upon it—like a social media post that somehow, against all odds, becomes a trend.
Athletes, too, are getting in on the act, grappling with the reality of a media landscape that expects them to be social media superstars. Younger players might roll their eyes at the thought of TikTok, while veterans have to be coaxed into sharing more than just a picture of their dinner. Second City Works provides the guidance on how to do that authentically, so they don’t have to resort to posting sponsored content about protein shakes.
As the NHL’s deputy commissioner put it, “Second City just brings energy and humor!” Which, let’s be real, is exactly what the players need after a grueling season of oversized checks and over-the-top expectations. They’re turning serious topics into interactive sessions where candid conversations reign supreme—because who needs to focus on the game when you can workshop your personality?
Whether it’s coaching a Fortune 500 CEO on how not to sound like a robot during presentations or helping a rookie understand social media without their cringe meter exploding, Second City Works customizes content that meets the moment. Remember, improv is all about listening—and always having a snarky comeback ready for the audience.
It’s a delicate balance of genuine connection and performance, mirroring the structure of comedy. After all, engaging with the media isn’t just about landing a witty answer; it’s about making sure you don’t end up looking like a deer caught in headlights. Because let’s face it, failing to engage could very well spell the end of your corporate career—or at least make you the subject of a late-night talk show segment.
This saga appeared lovingly crafted in the Oct. 22 issue of The Hollywood Reporter magazine. Click here to subscribe and learn more about the absurdity of corporate improv.
