From Michigan Ross to Retail Revolution: Stitch Fix CEO Matt Baer Shows How AI Empowers Personal Style

A proud Michigan Ross alum, Baer is known for his action-oriented, forward-focused leadership style. His leadership has taken him across continents, disciplines, and industry verticals, scaling operations and building diverse, talented teams. During his conversation with Sharon F. Matusik, the Edward J. Frey Dean of Business at Ross, attendees gained valuable insights into Baer’s business acumen and personal journey, and he also provided advice for future business leaders. 

A Personal Journey Shaped by Technology and Risk

Baer’s retail roots trace back to his family’s furniture business in Florida. In his talk with Dean Matusik, he recalled that, in the late 1990s, e-commerce was a tough sell. But Baer saw the opportunity to use technology to deliver a better customer experience. That vision ultimately became his personal pursuit, and he left a lucrative legal career path to explore it.

That risk paid off. 

After working at three retail startups, one of which Baer led to unicorn status, he took a leadership position at Walmart, where he played a critical role in transforming Walmart’s digital business. After Walmart, he led the long-term digital strategy for both Macy's and Bloomingdale's, while driving initiatives to deepen customer relationships. Today, he’s at the helm of Stitch Fix, the leading personal styling service.

Stitch Fix: Disrupting Retail

Baer was drawn to Stitch Fix because he saw a unique opportunity to continue his pursuit of innovation and to leverage the company’s strategic advantage: deep client knowledge.  

“In retail, there's this holy grail out there, and that's how much you know about your client. At Stitch Fix, before your very first transaction, we know everything about your style preferences. We know everything about your fit. We know everything about your budget preferences, and that gives us this very unique competitive advantage,” said Baer.  

We are taking something that is so personal—your individual style—and using AI and data science to create unprecedented client experiences that no other retailer can touch.

Leveraging AI Across Its Business

Baer shared that Stitch Fix was an early adopter of AI and that the company uses it across its business, from inventory management to merchandise product design and client experiences. At Stitch Fix, AI is used as a valuable tool to empower the team, and the company is currently executing or exploring hundreds of AI-use cases.

One example is Stitch Fix Vision, a style-visualization tool that provides clients with GenAI imagery of them in the latest styles and trends based on their own style profile.

The Irreplaceable Human Element

While Baer spent a lot of time sharing how the company uses AI to create better client experiences, he also reinforced the importance of the human element in building brand trust.

Human empathy is critical to building personal relationships between our stylists and clients. That’s at the core of everything we do. Even as we innovate with technology, the importance of keeping humans in the loop—especially in such a personal domain as clothing—is what sets us apart.

Baer knows firsthand how powerful the relationships between clients and stylists are, as he is a stylist himself.

“It’s really remarkable the relationships you build as a stylist,” he shared. “You're the first person to find out whether your client is expecting, whether their son or daughter is getting married, or whether they are moving to a new geography. There's a human element there where they're excited to tell you. They have that unique trust or bond with you.

We're going to continue to lean in and continue to build platforms that empower both the stylist and the client. We’ll have AI-driven experiences and human-driven service.”

Leadership Lessons and Advice for Students

When asked if Baer’s hiring philosophy has shifted in the age of AI, his answer was an emphatic no. He shared how AI is a skill that can be learned, and will be learned, by those who embody what he’s always looked for: intellectual curiosity, entrepreneurial spirit, strong communication skills, grit, and passion.

He closed his talk by urging Ross students to pursue happiness and fulfillment, not just financial reward. “Those who follow their passion end up in the right place,” he said, reminding the crowd that confidence and self-trust are critical to success

Ross Momentum and AI in Business

Dean Matusik highlighted Ross’s ongoing efforts to explore AI’s role in business and society. The 2026 AI Business Transformation Speaker Series offers students the opportunity to learn from visionaries shaping manufacturing, retail, and beyond—including Matt Baer and Mary Barra, GM's CEO. As AI redefines every industry, insights from alumni like Baer help propel Michigan Ross—and its students—into the future.

Culture, Curiosity, and Courage

Baer’s journey from Ross BBA to CEO of Stitch Fix isn’t just a story about retail disruption—it’s about leadership, risk-taking, and the power of pairing innovative technology with authentic human connection. As he told students, the real magic happens when you trust yourself and pursue what makes you happiest.

Whether you’re shopping for clothes or charting your own career path, Ross alumni like Baer are proof that culture, curiosity, and courage are truly in style.

About 100 students, faculty, and staff attended Baer's talk on February 23, 2026, including undergraduate and graduate students from multiple Ross degree programs. Students from across the university also attended, including those involved in the Michigan Fashion Summit.