The Creative Leader Behind Urban Outfitters

A sit down with Urban Outfitters' Head of Brand Marketing & Communications, Cyntia Leo

Author

Carlo Palomino
May 09, 2025

Welcome back to The Friday Fortune! The sun is out, the iced coffee’s kicked in, and the group chats are already scheming Memorial Day plans, which means it’s officially time for your favorite end-of-week distraction. Step away from the 97 tabs you swear you’re getting to.

We’ve got stories that will make you laugh, rethink your career path, and possibly start a five-year vision board.

Each week, we spotlight bold thinkers, creative risk-takers, and CMOs who actually like spreadsheets (and somehow still have taste). This week is no exception.

Here’s what’s on deck this week:

  • A deep dive with Cyntia Leo, Head of Brand Marketing & Comms at Urban Outfitters

  • Manscaped’s successful partnership with OpenFortune

  • How Sprite surpassed Pepsi as the third most popular soda in the U.S.

📈 Marketer of the Week

If there’s anyone combining creative soul with cultural savviness, it’s Cyntia Leo, Head of Brand Marketing & Communications at Urban Outfitters.

With a background that spans Disney magic, Nike grit, and now leading Urban’s next chapter, Cyntia’s journey reflects her authenticity, daring creativity, and deep conviction that stories bring people together.

Growing up in Washington Heights in a traditional Dominican-Chinese household, Cyntia was expected to follow a practical path. Think accounting or education. But an unexpected ticket to The Lion King on Broadway changed everything. That moment lit a creative fire that would guide her into high school theater, marching band, and eventually The New School, where she pursued cultural and media studies on a full scholarship.

Her first writing gig? Playgirl magazine—a detail that raised more than a few eyebrows at home. But Cyntia was chasing her voice, wherever it led. That voice brought her to Disney, and serendipitously, back to the very stage where she’d watched The Lion King as a child. It was her first real taste of full-circle magic.

Cyntia had always been an athlete, and while her Disney role gave her access to show-stopping moments, it didn’t scratch her competitive itch. That pull led her to Nike, where she spent over ten years shaping experiences and campaigns that lived at the intersection of sport, culture, and emotion. At Nike, Cyntia helped launch major campaigns like Virgil Abloh’s Off-White collaboration and produced events that brought out icons like Serena Williams, Maria Sharapova, and Andre Agassi for a street-side tennis match in NYC.

Her bold ideas didn’t go unnoticed. She transitioned from experiential roles to brand marketing, embracing the opportunity to set the narrative, shape strategy, and lead cross-functional teams. “You are essentially creating the strategy and the vision of the message you want to get to your consumer,” she explained. This shift positioned her as a true quarterback, guiding everything from social content to store activations with a clear sense of purpose.

When it came time to leave Nike, she turned to her trusted five-year plan. Her next move needed to align with her energy drivers, her personal values, and her purpose: creating space for kids who look like her to imagine bigger futures. Urban Outfitters checked every box. As a college student in New York, the Union Square store had been a sanctuary of self-expression and creativity. Now, she had the chance to shape its future.

At Urban, Cyntia is focused on reaching the next generation, bringing a modern spin to the brand’s legacy while preserving the tactile magic of in-store discovery. She's not interested in sticking to conventional campaigns either. Her approach is experimental, purpose-driven, and refreshingly real. “We want to be unexpected,” she shared, hinting at what’s to come.

Cyntia’s Takeaway

“Hold onto your voice… but make sure you’re backing that up with strategy and data.” That’s the advice she gives to women navigating leadership and it’s advice she lives by. She’s also a fierce advocate for normalizing discussions around working motherhood, sharing her journey through IVF and the emotional balancing act of career and parenthood with vulnerability and strength.

To hear how Cyntia Leo is reshaping Urban Outfitters through empathy, edge, and unapologetic creativity, listen to the full episode of CMO Weekly.

Crack open a handful of the week’s best marketing links—because good fortune favors the curious.

That’s a wrap for this week’s Friday fortune.

If you enjoyed the read, pass it along to your favorite marketer who could use a little extra inspo in their inbox.

Until next time, may your marketing be memorable and your cookies always be fortunate!

— The OpenFortune team