Wayfair CMO Paul Toms isn’t quietly inching into the AI era—he’s rearchitecting the entire customer journey around it. From personalized discovery to real-world measurement, the brand launched an AI-powered “Discover” tab this summer that lets users visualize their dream rooms and then shop the look. Backed by large language models and a hefty product catalog of 30+ million items, the experience is built to solve the paralysis of choice—and turn inspiration into transaction with minimal friction. Toms, working closely with CTO Fiona Tan, ensured the marketing arm was dialed into tech development from day one.
He’s also eyeing a future beyond phones and screens where purchases might be made via wearables or voice. It’s a bold vision, but Toms knows that with every new platform comes the marketing challenge to match. That’s why he’s leaning on AI to map the messy, cross-channel customer journey—from social click to final cart. Traditional metrics aren’t cutting it in this fragmented environment, so Wayfair is now tracking first-party signals to figure out what’s actually driving business impact. For Toms, success isn’t about staying early—it’s about staying measurable.
Perhaps most radically, he’s broken down the wall between creative and media teams. Instead of handing over assets and hoping for the best, creatives are now responsible for tracking performance, spotting trends, and adjusting in real time—all with a little help from AI. This feedback loop has accelerated testing cycles and created a culture where everyone owns the outcome. Is AI finally helping to bridge the gap between the art and science of marketing?

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