Good morning. As AI shopping agents become more sophisticated and widely adopted, the retail landscape is poised for dramatic change.
These agents may soon make purchases online just as often as human customers—a topic my Fortune colleague Jason Del Rey explores in his new article, “How Amazon and Walmart’s retail dominance could be disrupted by ChatGPT and Perplexity.”
Del Rey spoke with Scot Wingo, an expert in e-commerce disruption and founder of ReFiBuy (short for research, find, buy). Wingo’s company is developing software to help consumer brands and retailers adapt to an emerging online landscape where AI shopping agents are as active as human shoppers. “Wingo is perhaps more bullish than many about how soon and severely new AI shopping tools may disrupt existing e-commerce giants and legacy retailers alike,” Del Rey writes.
Wingo says large language model companies such as ChatGPT and Perplexity are gaining significant consumer attention and, as a result, broad distribution. “When you get that consumer distribution, you have to figure out how to monetize it,” he explains. “It’s become pretty apparent to me—especially when Perplexity launched their first shopping feature—that this was going to be the next big wave of e-commerce.”
Wingo said Amazon’s new AI features, like its Rufus AI shopping assistant, are good efforts, but he believes ChatGPT will ultimately prove better. “For Rufus to improve dramatically, it would almost have to replace the existing search experience on Amazon,” he told Del Rey. “And that’s a chasm Amazon’s not going to cross because that would kill $60 billion of advertising revenue that’s essentially pure profit margin.”
Walmart, meanwhile, plans to take an open approach to shopping agents and welcome them. “In a way, that’s smart because they’re a challenger to Amazon, and I don’t think they have anything to lose,” Wingo says. For more on his recommendations for retailers and brands—including how their operations need to change—you can read Del Ray’s complete article here.
In the first quarter of 2025, Walmart’s e-commerce business reached profitability for the first time. E-commerce grew more than 20% across each segment of the enterprise, with consumers willing to pay for faster delivery despite the uncertain macroenvironment. During Oppenheimer & Co.’s annual consumer growth and e-commerce conference on June 9, Walmart EVP and CFO John David Rainey said he views this growth as sustainable.
“We’re now allowing customers to shop with us in the way they want,” Rainey said. “If you’ve got more eyeballs coming to our websites, you’re going to have more marketplace sellers wanting to sell there, more advertisers wanting to pitch their products there.” He added, “I feel like this is all working together within the broader omni ecosystem that we have, and I don’t see this stopping. I think we’ll continue to have the progress that we’ve seen here.”
The future of e-commerce is arriving fast—and retailers may soon find that some of their most loyal customers are AI agents.
Sheryl Estrada
sheryl.estrada@fortune.com
Leaderboard
Dave Bragg was appointed CFO of UDR, Inc. (NYSE: UDR), a multifamily real estate investment trust, effective July 24. Bragg succeeds Joe Fisher, who in January was appointed chief investment officer in addition to his responsibilities as the company’s president. Bragg brings over two decades of experience. He joins UDR from Roots Management Group, most recently serving as CFO and previously as chief strategy officer and head of investment management. Before that, Bragg served as managing director at Green Street.
Tarek Robbiati was appointed CFO of Pure Storage (NYSE: PSTG), an IT provider of data storage technology. Robbiati has more than 25 years of financial and leadership experience in the global technology sector. Robbiati has served in various business and financial leadership roles, including as CEO of RingCentral. Before that, he was the CFO of Hewlett Packard Enterprise Company (HPE). Prior to HPE, Robbiati served as CFO at Sprint Corporation.
Big Deal
Finance leaders are taking different approaches to tariffs based on their industries, according to Grant Thornton’s Q2 2025 CFO survey of over 260 respondents. Bankers are focusing on scenario planning and are concerned about a slowdown in M&A activity. Manufacturers are adjusting supply chains and renegotiating contracts to manage price volatility. In tech and telecom, leaders are turning to automation and AI to cut costs, though some clients are scaling back spending.
The survey also found a sharp increase in focus on customers: 53% of finance leaders are boosting sales and marketing budgets (up 13 points from last quarter), and 51% now rank customer acquisition and retention as a top priority.
Going deeper
“Trump says U.S. could send letters setting tariff rates rather than extend deadline—‘Dear Mr. Japan, here’s the story’” is a Fortune report by Jason Ma.
From the report: “President Donald Trump said that although trade negotiations are still ongoing, he would rather send countries a letter that lays out the tariff rates they face and not extend the July 9 deadline, when the halt on his ‘reciprocal tariffs’ will expire. Trump previously vowed to send similar letters in May and earlier this month, though talks continued.”
Overheard
“If you think you’re a failure, you’ll fail. If you think you’re a winner, you’ll win.”
—Sports legend Billie Jean King, 81, the American former world No. 1 women’s tennis player, told Fortune in an interview. According to King, the top 1% of professionals preach positivity to themselves. Much like Gen Z, who are proponents of manifesting success, King agrees that there’s power in thinking positively.
