Pinterest CEO Bill Ready Is Taking Big Swings to Win Gen Z
Pinterest operates on what Ready calls a taste graph, meaning it doesn’t trust AI to make style recommendations, but does use the tech to pull what other Pinterest users have curated and suggest a similar outfit to others, Ready explains. “The AI on its own would say things like, ‘Oh, you picked a handbag in this pattern. So here’s a dress and a pair of shoes in the same pattern.’ But how many people dress that way?”
Gen Zs are also increasingly engaging with AI chatbots to assist them in their shopping journeys.
Three‑quarters of Gen Zs say they’ve used a generative AI tool like ChatGPT, Gemini or Midjourney, with 58% using these tools at least weekly. Gen Zs are twice as likely to research products via AI‑powered assistants or chatbots (34% of Gen Zs vs 17% of millennials), according to Archrival data.
Pinterest launched its own AI chatbot, the Pinterest Assistant, in the US in late October. Being in London, I can’t yet try, but Ready explains how it’s differentiated from other AI models. “Most chatbots, if you ask them for shopping advice, they’ll respond with a PhD thesis. We want our assistant to be more like the person you love shopping with, you know, the sister, the best friend, or the great rep at the boutique,” he says. “If you ask them, ‘Hey, I’m looking for the killer outfit for the holiday party,’ they will find something based on your taste that looks great on you.”
Ready is also keen to resist removing all the friction from the shopping experience. Two weeks ago, Shopify announced “agentic” storefronts, signaling a future where AI agents will complete the entire purchase journey for its users. “When [agentic providers] say ‘great news’, this AI agent will just go do all your shopping for you. [But] I look at that and say, you’re building shopping for people who hate shopping,” he explains. “We want to build shopping for people who love shopping, which means don’t automate it all the way. We want to give the friendly assist, but let [our users] be in the driver’s seat.”
As the market changes — and as consumer behavior evolves — Ready is ready to adapt. “We’ve hit a major scale. “We have more than 600 million users,” he tells me. “We’re big enough to matter; we’re big enough that we can influence the industry, influence culture and taste and what’s appropriate in these places, but we’re small enough that the die is not yet cast, and I think that’s a really, really interesting place to be.”
