Nov 03 2025
Artificial Intelligence

Money20/20 2025: How AI Is Changing the Way We Shop

Retailers are driving personalization efforts powered by artificial intelligence to enhance the shopping experience.

Artificial intelligence may not be as new to the retail sector as it is to many other industries — chatbots have been a staple of the retail customer service experience for years. But with the rise of agentic AI, new and powerful use cases are poised to make some pretty big waves.

IT leaders shared their thoughts on how AI will impact retail in a panel discussion at Money20/20 titled, “The Future of Shopping: How AI and Agents Will Rewrite the Rules of Commerce.” The panel discussion was moderated by J.D. Durkin, news host and NYSE journalist, and featured Michelle Gill, executive vice president and general manager of small business and financial services at PayPal; Matt Renner, chief revenue officer at Google Cloud; and Jody Kalmbach, group vice president for digital experience and e-commerce at Kroger.

Introducing the discussion, Durkin acknowledged that it was tough to have a conversation at Money20/20 without mentioning AI, and noted that even casual conversations are beginning to shift toward agentic AI. “When we consider what agents and commerce means, it sort of paints a picture of the future where AI assistants manage shopping, basically, start to finish.”

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AI Agents Can Usher in an Era of Increased Personalization

Renner began by noting the heightened expectations that retail shoppers have, saying, “I think one piece of it is just the constant strive to get more personal to the customer and how their expectations continue to go higher and higher.”

Kalmbach explained how that level of personalization is being realized at Kroger. “One of the things that’s been foundational for us was our loyalty program. And what was so important about that is that has now created this data asset that has really become foundational to the entire agentic commerce experience.”

The volume of data Kroger has been able to collect is allowing the company to hyperpersonalize its interactions with customers. “We have about a billion personalized touch points every month with customers, but many of those are sort of reactionary based on data that the customer has given us. We now have this new agentic shopping chapter. We’re really turning into something that’s much more proactive, something that can anticipate needs.”

Kalmbach also said Kroger sees agentic AI driving brand loyalty through increased personalization. “If you look at grocery shopping historically, it was a functional experience. You have your list, you go in, you buy your groceries. This next chapter, we’re really going into something that’s going to be much a more inspirational, more emotional connection with customers, deepening loyalty and actually expanding a relationship through discovery.”

The plan is to find ways AI agents can do more than just filling a customer’s grocery list. Services could expand to help with meal planning that involves dietary restrictions so that “agents are going to help solve problems for customers, develop the right plan and take it all the way through that e-commerce transaction.”

WATCH: Find out how to keep your agentic artificial intelligence use cases secure.

How AI Agents Can Reduce Friction To Make Shopping More Seamless

The benefits of agentic AI go beyond personalization and brand loyalty, however. Kalmbach spoke about the possibility of reducing friction in an omnichannel shopping experience so customers can go all the way from the discovery process to a final purchase in one visit.

“It’s really challenging to think about the start and finish all in one place, and yet, we’ve seen and expect that 40% of consumers for this holiday season will start their discovery online,” Gill said. “Wouldn't it be wonderful if, within that contextual first conversation that is personalized, they did complete that transaction as well, and you wouldn’t have all of this drop-off that happens in between.”

But Gill noted some significant challenges for merchants, such as how to ensure continued access to their data and their consumers while delivering a pleasant post-purchase experience that can bring back customers not only online but to physical stores, as well. “As we think about the rails that we’re collectively building and the protocols, it’s how do you make that experience seamless, but at the same time continue to give merchants control, and allow consumers to have the delightful experiences that they’ve come to expect.”

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Shoppers Demand Convenience, But They Also Require Trust

As with any AI use case, for any of these shopping enhancements to be successful, the underlying data must be kept secure.

Gill spoke about data security in terms of a seamless experience delivered with trust: “Consumers have expectations to be in lots of different services for lots of different reasons today, and we need to allow our merchants to serve consumers where they are. In an age where data and data privacy has become such a critical need for consumers, in particular, the notion of, ‘Which agents am I going to trust with my personalized data?’”

“This notion of trust and the depth and the time that you’ve been in market is actually pretty critical. And this notion of who are you going to trust with your personalized financials, I think it’s a really big thing,” Gill said.

Kalmbach agreed on the importance of consumer trust when offering advice to other retailers considering agentic AI: “Some of you may remember from decades ago when people were like, ‘Do you think e-commerce is here to stay?’ E-commerce is here to stay, and agentic shopping is going to continue to accelerate it. It’s probably the fastest acceleration we’ve seen in the consumer change.” 

But to harness that change to drive business success, she said, it’s critical to “build the right foundation, with data governance and all the other pieces. And then, line up that ecosystem that’s going to give you the confidence that you’ve got the right partners, but also that you can accelerate at pace.”

Keep this page bookmarked for articles from the event, and follow event highlights and behind-the-scenes moments on the social platform X @BizTechMagazine at @money2020.

Photography by Joe Kuehne
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