New York —

When Jamie Iannone took over as eBay’s chief executive in early 2020, the company had undergone a leadership shakeup and was in the process of shedding businesses under pressure from activist investors. One of the internet’s original shopping sites, it had just lost its position as the second largest ecommerce platform to Walmart amid a decline in relevance.

But it soon got a boost from the Covid-19 pandemic. And now, the company wants to build on that momentum by investing in artificial intelligence. This year alone, eBay has introduced five new AI features, including AI-backed shipping estimates and a shopping chatbot, as well as a partnership with ChatGPT-maker OpenAI.

Investors appear optimistic about the strategy. eBay’s stock has surged 75% since 2020; this year, its shares are up more than those of tech heavyweights Microsoft, Meta and Amazon.

Still, reinventing a 30-year-old online marketplace is no small task, especially co

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