Confidence, Curiosity, and Commerce: Fiona Bora ’98 Shares Her Journey

From the classrooms and playing fields of Baldwin to executive leadership roles at some of the world’s most recognized retail brands, Fiona Bora ’98 has built a career defined by curiosity, analytical thinking, and creative leadership.

 

Today, Fiona serves as Chief Merchandising Officer at Tuckernuck, where she leads merchandising strategy and drives growth through data-driven decision-making and operational excellence. Before joining Tuckernuck, she held senior leadership roles at Nordstrom and Ralph Lauren, overseeing billion-dollar businesses and helping guide major retail transformations. Reflecting on her time at Baldwin, Fiona credits the School with helping her find her voice and develop the confidence that would shape her career.

 

“I loved Baldwin. Truly,” she shared. “It was an environment where being smart, curious, driven, funny, competitive, weird, creative — all of it — was celebrated.”

 

A three-sport athlete who played field hockey, lacrosse, and swam, Fiona says Baldwin encouraged students to think independently and speak confidently. “What Baldwin really gave me was the confidence to find my voice,” she said. “We were encouraged to speak up and challenge ideas. That foundation has stayed with me throughout my career.”

 

Fiona also vividly remembers the teachers who challenged and inspired her. “Mrs. Pressman in History — I can still name major Supreme Court rulings in chronological order, which feels both impressive and slightly concerning,” she joked. “Madame O’Neal in French. Mrs. Keshishian in Latin. Mrs. Cairns and Dr. Ledlie in English. Mrs. Willis in Math. Mrs. Pethick in Jewelry. I could keep going! They were brilliant, but more importantly, they challenged us, and they taught us how to think critically, write clearly, communicate effectively, and defend our ideas. Those are leadership skills.”

 

After Baldwin, Fiona attended the Wharton School of the University of Pennsylvania as a Nelson Scholar, studying Finance, Management, and Legal Studies. She later completed executive education at Massachusetts Institute of Technology focused on blockchain and artificial intelligence.

 

“I was incredibly lucky to be a Nelson Scholar, largely because I was good at math, and oddly enough, being good at math gave me the confidence to believe I could be good at other things too,” she explained. “There’s something powerful about learning how to solve problems logically. It teaches you not to panic, to make decisions, and to keep moving forward.”

 

What motivated her to explore the areas of blockchain and artificial intelligence (AI)? “You have to stay savvy,” Fiona explained. “Retail, technology, consumer behavior — everything moves fast, and I never want to be the person saying, ‘Wait, what’s happening?’”

 

According to Fiona, data analytics and online retail changed everything. “Now you can see exactly where customers click, what they linger on, what converts, what gets returned, what works in one region versus another,” she explains. “It’s honestly wild compared to how retail operated years ago. The speed is also completely different now. Today, brands can react much faster, test ideas more quickly, and adapt in real time. The art still matters enormously, but now the science behind it is much sharper.”

 

Her passion for retail began with a fascination for consumer behavior and the intersection of creativity and business. “I’ve always been fascinated by how people spend their money, what they value, what makes them feel confident or aspirational,” she said. “Also, I had a fairly serious shopping habit, so retail felt like a natural fit. If you have the opportunity to spend your days around beautiful things, inspiring environments, creativity, color, design, and storytelling … why wouldn’t you choose that? Retail at its best is incredibly inspiring.”

 

Throughout her career, Fiona has become known for balancing creative instinct with analytical rigor. Her leadership philosophy is grounded in recognizing patterns, moving quickly, and staying adaptable.

 

At Tuckernuck, Fiona approaches merchandising with a blend of intuition and data. “I’d say 80% of decisions should be driven by data and 20% should be driven by instinct,” she said. “Hopefully, those instinct-driven decisions become the next wave of data because you spotted something before everyone else did.”

 

She also credits collaboration and strong teams as essential to success. “The best teams challenge each other, communicate openly, and keep learning,” Fiona said. “I also believe strongly in surrounding yourself with people who are smarter than you in different areas.”

 

As technology continues to transform retail, Fiona remains energized by the possibilities of AI and emerging tools, especially their ability to expand creativity and accelerate innovation. “What’s fascinating is how accessible creativity has become,” she said. “You can now use Computer-Aided Design (CAD) in seconds — literally anyone can experiment with design ideas, concepts, silhouettes, prints, all of it, so instead of hand-sketching, you’re digitally building and visualizing products. That democratization of creativity is cool.”

 

For Fiona, however, the heart of retail still comes back to people. “I love seeing someone feel beautiful and confident in something I helped bring to life,” she shared. “Feeling good in what you’re wearing matters.”

 

That connection to community made it especially meaningful to see Tuckernuck pieces featured in the Baldwin Boutique. “Radhika Cobb (P ’34) has done such an amazing job curating everything for Baldwin’s Boutique. I’m genuinely proud of what she’s built. Seeing Tuckernuck represented at Baldwin feels very full-circle for me,” Fiona said. “Baldwin was such an important part of my life, so being able to contribute in some small way back to the community is really special.”

 

Her advice to current Baldwin students interested in leadership or retail is simple and direct:

“Go work in a store,” she said. “Observe customers. Watch how people shop, what frustrates them, what excites them, what makes them hesitate, what makes them buy. The best retailers understand human behavior, and there’s no substitute for seeing it firsthand. Almost every great merchant or retail leader started on a sales floor somewhere.”