A conversation with Fiona Tan, Chief Technology Officer of Wayfair.
Our Executive Function series features perspectives from leaders driving transformation through AI.
Wayfair(opens in a new window) is a U.S. ecommerce company based in Boston, Massachusetts, specializing in selling a wide range of furniture, home decor, and other household goods online and, more recently, in physical stores. We spoke with Fiona Tan, Chief Technology Officer, about AI reshaping the customer experience, streamlining operations, and its impact on employee upskilling.
What priorities made it important for Wayfair to invest in AI?
At Wayfair, strategy drives everything. We start by identifying areas where AI can enhance efficiency, accelerate processes, or innovate the customer experience.
As a digitally native ecommerce retailer, marketing was one of our earliest AI applications—specifically, optimizing ad spend and improving attribution. We focused on traditional machine learning techniques, such as predictive modeling. The early work provided a strong foundation for Wayfair’s broader AI adoption over the past several years.
Today, AI plays a pivotal role not just in marketing, but also in areas like supply chain optimization, product recommendations, and customer experience design.
The rise in popularity of OpenAI has significantly increased our emphasis on AI, pushing us to explore more advanced applications and leverage new capabilities.
“We really think about our company strategy first, and then underneath it, which are the areas AI can help accelerate, disrupt, etc.”
Why do you think AI is especially critical for ecommerce?
Personalization has always been a major goal in ecommerce. AI has allowed us to move beyond basic keyword-based searches to sophisticated conversational interfaces.
For example, multimodal AI integrates text, images, and customer preferences, enabling a richer and more personalized shopping experience. This is especially crucial for product categories like ours, where items are often unbranded and slightly more difficult to describe—think of a “green couch” rather than a familiar AA battery brand.
AI helps us enrich our product catalog and deliver more meaningful customer interactions.
Beyond customer improvements, how is Wayfair fostering AI fluency within the organization?
We’ve developed specialized training programs for both technical and non-technical teams. For technologists, the focus is on equipping them with advanced tools and skills. For non-technical teams, like legal or HR, the goal is to unlock productivity through tailored training. Often, these teams identify use cases that technologists might not foresee. For example, our legal team uses AI to analyze customer feedback for potential risks, such as product safety concerns.
Generative AI has also been instrumental in addressing technical debt. Legacy systems and databases, which are traditionally neglected due to their complexity, can now be modernized with AI tools. These capabilities allow us to accelerate projects that would have otherwise been resource-intensive.
How do you measure the success of these AI initiatives?
The impact has been clear. Our legal team has drastically reduced the time required to review customer reviews for liability concerns while improving accuracy. On the technical side, AI has enabled us to understand and modernize outdated codebases, saving time and resources. In one instance, we were able to create new APIs 85% faster as a result.
Additionally, generative AI is enriching our product data, ensuring higher accuracy and better customer experiences.
“…because of the nature of generative AI, and the capabilities there, I would say that the training for the general population is potentially even more important.”
What’s next for AI at Wayfair?
The potential applications are nearly limitless. As models grow more advanced, we’re exploring agentic capabilities that could handle complex tasks autonomously. We’re also committed to empowering every department, from finance to operations, to creatively leverage AI.
Beyond internal use, we’re focused on transforming customer experiences. By integrating conversational interfaces, multimodal search capabilities, and hyper-personalization, we aim to set new standards for ecommerce.
“Inasmuch as we can allow folks to become more and more familiar with what the capabilities are, it’ll allow us to make some of these disruptive changes.”
How do you see AI reshaping the future of ecommerce?
I envision two distinct trends.
For straightforward needs, customers will rely on conversational AI for quick, precise purchases.
On the other hand, immersive, interactive shopping experiences will become increasingly prevalent, offering personalized recommendations and inspiration through advanced technologies like AI-powered video and image searches. Meeting customers where they are—whether they want efficiency or a rich shopping journey—is the future.
AI will also play a critical role in backend operations, optimizing everything from supply chains to customer service workflows, ensuring a seamless and consistent experience.
By blending operational efficiency with customer-centric innovation, Wayfair is building an ecommerce ecosystem that not only meets but exceeds customer expectations. AI is at the core of this vision, driving transformative changes across every facet of the shopping experience and positioning us as a leader in the industry.
“We’re committed to empowering every department, from finance to operations, to creatively leverage AI.”
Wayfair uses ChatGPT across its organization in departments like legal, research, and marketing. The company also powers its customer service platform using OpenAI APIs.
