Wayfair’s Fiona Tan on building teams and transforming how customers shop

Fiona Tan will be celebrated at the NRF Foundation Honors as one of the dynamic leaders on The List of People Shaping Retail’s Future 2027.

Technology is transforming how consumers shop, but the most exciting innovations aren't just about making things faster or easier; they're about creating experiences that better reflect what customers actually want. Wayfair Chief Technology Officer Fiona Tan joins Retail Gets Real to discuss the future of retail technology, the importance of building strong teams and how retailers can embrace innovation while keeping customers at the center of everything they do.

Wayfair Chief Technology Officer Fiona Tan

From solving puzzles to transforming retail

Tan's passion for technology began at MIT, where her first computer science class introduced her to a career built around solving problems. After starting as a software engineer at Oracle and spending years developing enterprise technology, she made the leap into consumer-facing retail technology at Walmart, where innovations like online grocery ordering, pickup and delivery made the results of complex engineering work tangible to millions of customers. Solving difficult problems is exciting, but seeing those solutions improve the customer experience makes the work even more meaningful.

Building successful teams starts with strong leadership

Leading global technology teams requires more than technical expertise. Tan credits her experience playing competitive sports with shaping her approach to leadership, particularly the importance of teamwork and playing to people's strengths.

"I feel like if you develop your team and if you help make them successful, then you're successful," Tan says.

A leader's success comes from helping others succeed — assembling strong teams, removing obstacles and creating an environment where colleagues support one another. That means having the right answer isn't enough if others don't understand the thinking behind it. Providing context, explaining ideas clearly and recognizing that people process information differently are essential skills for anyone moving into leadership.

Making shopping more intuitive with technology

With technology evolving faster than ever, retailers face the challenge of deciding which innovations are worth pursuing and which may not be ready for widespread adoption. Tan encourages her teams to take a hands-on approach by experimenting with emerging tools, reading research and learning directly from people working on complex technical challenges.

One of the biggest opportunities lies in changing how customers discover products online. Traditionally, shoppers have had to adapt to retailers' systems, using specific keywords, categories and filters to find what they need. New technologies are making it possible to reverse that relationship, allowing customers to express what they're looking for naturally while retailers do the work of understanding their intent. At Wayfair, that includes exploring more inspirational shopping experiences using natural language, images and video.

Embracing opportunities and the future of retail

Recently named to the NRF Foundation’s List of People Shaping Retail’s Future, Tan sees the honor as a reflection of her team's work at Wayfair and the importance of developing the next generation of leaders. Her advice for those building their careers is to embrace opportunities that feel uncomfortable, even when they aren't entirely sure they're ready.

Episode chapters

(00:00:00) From technology to retail

• How a passion for problem-solving led to a career in technology

• Early career lessons about teamwork and collaboration

• Why transitioning into retail technology was a big career risk

(00:05:06) Building strong teams through effective leadership

• The importance of recognizing individual strengths and encouraging teamwork

• Why a leader’s success depends on the success of their team

• The role of effective communication in becoming a better leader

(00:09:00) The rewards of solving problems in retail

• The satisfaction of tackling complex challenges and seeing results

• How retail technology innovations make a tangible difference in consumers’ lives

• Why embracing change is essential to succeeding in retail

(00:10:17) Navigating technology and innovation in retail

• Identifying which emerging innovations are worth pursuing

• How new technologies could transform the online shopping experience

• Why foundational technology and data remain essential for retailers

(00:14:22) How AI is reshaping shopping and product discovery

• Why AI-powered shopping is evolving differently than expected

• How new tools are changing the way consumers discover products

• Wayfair’s approach to creating more intuitive shopping experiences

Resources:

• Learn more about the NRF Foundation’s List of People Shaping Retail’s Future for 2027

• Get ready for Retail’s Big Show in NYC

• Become an NRF member and join the world’s largest retail trade association

• Find more episodes at retailgetsreal.com