Jason Del Rey has spent nearly two decades covering the companies and forces reshaping commerce—at Recode, at Fortune, and now through The Aisle, the publication he founded to focus on the intersection of AI and commerce. He also wrote the book on Amazon and Walmart. Literally.
When someone with that kind of resume leaves an established platform to launch their own publication squarely focused on AI in commerce, it’s a signal. The same conviction that led us to launch RetailClub led Jason to make a similar leap. Not because AI in commerce is a good story to tell. Because it’s the story.
In a recent conversation, Jason shared what he’s learned since making that call, and what he’s watching going forward.
It’s Not One Thing. It’s All of It, at the Same Time.
The case for AI in commerce isn’t built on any single development. It’s the convergence of several things happening simultaneously: consumers flooding AI apps and staying there, retailers building their own AI-powered concierge and assistant experiences, and a new generation of AI-native platforms emerging as potential sales channels.
As Jason put it: “It’s not just that the apps may become new sales channels. It’s not just that retailers are trying to figure out how they develop their own AI assistants. It’s that all of it is happening at the same time.”
That convergence is what makes this moment different from past technology cycles. There isn’t one stakeholder pulling everyone along. The energy and investment are coming from multiple directions at once.
And the starting point, in his view, is the consumer.
“I think it really is a case of working backward from customer behavior. How people are searching, how they’re researching products, how they’re expecting to be able to converse with a website or an app or customer service—all of that has changed.”
Whether or not everyday consumers end up checking out directly inside Gemini or an AI search interface, the underlying behavior shift is already real. That’s the foundation everything else is being built on.
The Talent Tension: AI Fluency vs. Institutional Knowledge
The conversation about AI in retail tends to focus outward—new sales channels, new customer experiences, new competitive threats. Jason thinks the internal transformation is just as significant, and maybe less understood.
It’s also creating real tension inside organizations. The people with the deepest institutional knowledge aren’t always the ones moving fastest with new tools. The people moving fastest don’t always have the context to apply them well.
Jason pointed to a conversation he had with DoorDash CEO Tony Xu that didn’t make it into his final Fortune story. Xu described the challenge of bringing in young talent who are now the AI experts, while retaining the value of machine learning specialists who’ve been with the company for a decade, and figuring out how to get those two groups not just to coexist, but to actually amplify each other.
“If a big tech-first organization is struggling with that, I think we’re going to see that in a lot of places.”
The leaders who will make careers in this moment, Jason argues, are the curious ones. Not necessarily the most senior, not necessarily the most technical, but the ones who thrive on uncertainty and are willing to move before everything is figured out.
Smart Retailers Are Engaging Early, Without Losing the Plot
There’s a version of AI strategy that’s focused on the press release or share price boost. Jason has seen enough of that to recognize when substance is missing.
The retailers he finds most credible are doing something harder: staying engaged with the major platforms while being honest with themselves about what actually drives their business today.
He recalled a conversation with leadership at The Home Depot. Their investment in delivery speed over the past year, and the returns it’s already generating, will dwarf anything an AI sales channel might produce over the next two years or longer. Same story at Lowe’s, where marketplace expansion is the real growth driver right now.
“The smartest companies are trying to be in the room with the conversations, and to get a little bit of the halo of being out on the frontier, but without diluting what really matters to them right now.”
That balance isn’t easy. There’s real value in being at the table when platforms like Google and OpenAI are building out commerce capabilities. Retailers who show up early get to shape the product, influence the data exchange, and establish positioning before it hardens. The ones who wait won’t just miss that window; they’ll find themselves on the wrong side of a gap that is going to widen quickly.
The winners and losers of the next decade are being sorted right now. But not at the cost of the fundamentals.
OpenAI Has More to Learn About Retail Than People Realized
The expectation, at least publicly, was that OpenAI’s move into commerce would be fast and decisive.
It hasn’t played out that way.
Jason has been “a little surprised by how much it seems like they have to learn.” The shopping-specific model came and went. Instant Checkout came and went. For a company with the resources and ambition of OpenAI, the pace of reversal has been notable.
“There’s only so much experimentation in public that you want a partner to be doing that doesn’t work out.”
The agentic commerce space certainly isn’t dead. But it’s messier and earlier than the headlines first suggested.
The Amazon-Walmart Question Is Getting Interesting Again
Two companies Jason has covered most in depth are now approaching AI from fundamentally different directions.
Amazon is still taking a controlled approach, and while they’re in conversations with third-party agents, CEO Andy Jassy has said those agents need to deliver a better shopping experience before Amazon opens up.
Walmart has moved aggressively in the opposite direction by striking partnerships with Open AI, Google, and Microsoft. The posture is open and collaborative.
“That dynamic between the two is always going to be somewhere I want to spend time.”
The Pace of Change Is Accelerating. The Window to Act Is Narrowing.
It’s been about a year since Jason launched The Aisle and we founded RetailClub. Both of us were hearing the same thing from people around us: aren’t you too early?
We weren’t. And Jason’s read on where we are now reflects that.
We’re past the moment of “is this real?” The experiments are real. The investments are real. The consumer behavior shift is real. But we’re still early enough that the proven playbooks, the clear winners, and the obvious case studies are mostly ahead of us.
What’s changing is the speed. The gap between organizations moving now and those waiting for more certainty is already widening, and the rate at which it widens is accelerating. Decisions made in the next year or two will matter more than most leaders currently appreciate, because by the time the playbook is obvious, the positioning will already be set.
The leaders who’ll be in the best position aren’t necessarily the most resourced or the most tenured. They’re the ones who stay curious, stay in the room, and keep building.
Author
Krystina Gustafson
Co-Founder & Co-CEO, RetailClub
Krystina Gustafson is the Co-Founder and Co-CEO of RetailClub, the only retail event built on the conviction that AI isn’t just transforming the industry, but is reshaping the economy, society, and culture that underpin it. She was previously SVP of content at Shoptalk and Groceryshop, a retail reporter at CNBC, and a web editor at Women’s Wear Daily.