The Watson Weekly: eCommerce Strategy & News

The Swift–Kelce wedding turned into a marketing free-for-all, and Rick and Jessica sort the brands that pulled it off from the ones that face-planted. The Knot circled Madison Square Garden with billboard trucks. A fake antique-shop ad about furniture rolling into the arena still racked up 11,000 likes. From there they get into Target finally waking up to the marketplace it's ignored for years, an...

The era of the weird, different storefront is over. On Shopify, design that converts beats design that surprises. That is the argument in the third and final episode of our Enterprise Shopify series. Rick Watson sits down with Elara Verret, Chief Digital and Customer Officer at Reitmans, and Isaac Newton, Co-Founder of Pattern (part of Domaine). Reitmans is a 100-year-old retailer with roughly 400...

Every big commerce name put up growth in the first half of 2026. Rick's question is what it cost them. Shopify had its best quarter in years and passed $100 billion in GMV, though loan losses at Shopify Capital crept up over the same stretch. Amazon beat estimates and then turned around and spent $44.2 billion in three months on AI infrastructure. UPS is doing something stranger. It's shrinking re...

Half of 2026 is behind us. We went back through the first six months and split the big commerce and AI stories into two groups, the bold moves and the cold ones. Start with Anthropic. While the attention stayed on OpenAI, it kept its head down and aimed at one customer, the enterprise buyer. The Snowflake deal landed. Opus shipped over the holidays and picked up real developer momentum. Claude Cod...

Unified commerce is a data strategy first and a Shopify decision second. Rick Watson tests that idea with two operators who have lived it. In episode two of the Shopify roundtable series, Rick talks with Elara Verret, Chief Digital and Customer Officer of Reitmans and Max Rolon, CTO of Domaine, about what enterprise retail runs into on the way to unified commerce. They get into the back-end system...

This week on the Watson Weekly, four stories about who controls what you see and what you buy. Papa John's wanted to reach you the moment your fridge runs empty, so it bought the data to know when that happens. Instacart supplied it. The company confirms this is the first time it has handed first-party purchase data to a brand outside packaged goods, served on NBCU streaming inventory. The targeti...

Tourists flew in for the World Cup and went viral filming trips to Buc-ee's and Waffle House. Rick Watson and Jessica Lesesky unpack what that attention is actually worth, then move to two bigger bets. The Watson Weekly Weekend episode is sponsored by Avalara. Its Agentic Tax and Compliance automates behind-the-scenes work for ecommerce brands, enabling accurate checkout tax calculation, clearer t...

Most brands still evaluate enterprise Shopify on license cost. The operators in this conversation evaluate it on opportunity cost, and that reframe changes the whole decision. Rick Watson opens a three-part series on the business case for enterprise Shopify with three people who have actually run the migration. Elara Verrett, Chief Digital and Customer Officer at Reitmans made the move to get clos...

Shopify wants to be the checkout layer under every AI agent, and its Spring 2026 edition shipped 150-plus updates to prove it. Meanwhile air freight spot rates climbed 41% year over year while demand grew 4%. Somebody is paying for that gap. Shopify Spring 2026: building the plumbing for agents Checkout now runs inside Microsoft Copilot, paid with Shop Pay. There's a universal commerce protocol bu...

TikTok Shop moved $4.4 billion in beauty and wellness. Saks wants $9 billion by 2030. Castle claimed $1.4 billion and was worth $16 million. This week is about which numbers actually hold up. Three companies put big figures on the table. Only one of them earned it, and even that one comes with an asterisk. Rick Watson and Nick Kaplan have a thought provoking conversation on these 3 stories. TikTok...

Salesforce renamed Commerce Cloud to Agentforce Commerce and calls this its biggest release in years. Rebrand, or substance? Nitin Mangtani makes the case. Every enterprise vendor is bolting "agentic" onto its roadmap this year. Salesforce went further and renamed the whole product. Nitin Mangtani, who runs Commerce and Retail Cloud, came on to defend the release line by line. We get into Storefro...

She told investors $440M. The real number was $15.7M. This week: the CaaStle fraud, Walmart's Subway play, and Shopify's $5B bet. In this episode: Walmart + Subway. Walmart folded Subway into its delivery app, with express orders coming off the Subway counters already sitting inside its stores. Live now in six states (Connecticut, Florida, Georgia, Ohio, Pennsylvania, Texas), with roughly 1,400 lo...

This week on the Watson Weekly weekend edition, Rick Watson and Jessica Lesesky discuss: Shopify pushes its buyback to $5 billion while every other tech giant pours cash into AI. We ask the obvious question: built for the AI era, or built for the next earnings call? Then Apple's new Siri arrives at WWDC running on Google Gemini, a roughly $1 billion-a-year arrangement that sits next to the $20 bil...

Software agents are now the highest-converting shoppers on the web, and most stores are built to lock them out. Rick Watson sit down with Stripe's Danny Smith, who leads global agentic commerce solution architecture, to work through what changes when your buyer is a piece of software. The Watson Weekly interview is sponsored by Avalara - the agentic AI platform automating global tax and compliance...

It's June 8th, 2026, and Rick Watson breaks down the week's e-commerce news with his usual habit: put the press release down and look at the calendar. This week: Amazon yanks Prime Day forward to June 23rd–26th and blames the World Cup and America's 250th birthday. Rick isn't buying it. With Q2 closing June 30th and a nervous consumer pulling back, this looks like a P&L decision aimed squarely...

Rick Watson and Jessica Lesesky sit down to unpack a busy stretch across tech, shipping, and commerce. They open with Anthropic's confidential IPO filing, submitted to the SEC on June 1st, and what it signals about the AI lab's trajectory. After a $65 billion Series H that pushed its valuation to $965 billion, Anthropic now sits ahead of OpenAI on that measure, and Rick and Jessica dig into how it...

Christina Hagopian has spent 24 years running her own brand strategy and creative practice. In this episode she joins Rick Watson to explain why a brand is far more than a logo: it's what people think and feel about you before your message ever lands, and it has to trace back to a company's actual mission, vision, and values. She and Rick talk through the real and the overstated parts of AI in mar...

Rick Watson runs through a busy week in retail. Walmart posted a $177.8 billion quarter, with revenue up 7.3%, U.S. comps up 4.1%, and global e-commerce up 26%, yet free cash flow landed at negative $1.9B as automation capex climbed. Advertising grew 37%, marketplace sales jumped close to 50%, and new shoppers skewed upper-income. At Sam's Club, more trips but smaller baskets. Authentic Brands Gro...

Rick Watson and Jessica Lesesky break down Walmart's Q1 numbers and what they say about where retail is heading. Revenue was up 7.3%, U.S. comps rose 4.1%, and global e-commerce grew 26%, but the more telling figures sit elsewhere: advertising up 37% globally and the U.S. marketplace up nearly 50%. Rick and Jessica make the case that Walmart is quietly becoming a digital services business, pulling...

In this Watson Weekly interview episode, Rick Watson is joined by Lennart Stevens, VP of Product Management for Agentforce Commerce at Salesforce, who walks through Storefront Next, the latest evolution of Salesforce's commerce storefront. Storefront Next is built for developers and for a world where AI and agentic coding are the default. You can spin up a new storefront inside Business Manager wi...

Two big retail earnings reports, two very different stories. Home Depot grew total sales 4.8% to $41.77 billion, but comparable sales barely moved (up 0.6%) and net income slipped to $3.29 billion from $3.43 billion a year ago, a sign of margin pressure. Target posted the louder top line, with net sales up 6.7% to about $25.15 billion and comps up 5.6%. The catch: net income fell 24% to $781 milli...

Home Depot just told the market it's treading water, and Rick Watson and Jessica Lesesky dig into why the remodeling boom never showed up. People are tapping their home equity to consolidate debt, not rip out the bathroom. Paint and outdoor are fine. Lumber, flooring, mill work? Not so much. So Home Depot is quietly walking away from the consumer and betting the house on pros, HVAC, and a $700 bil...

The Watson Weekly for May 18, 2026. Amazon launched a 30-minute delivery to take on DoorDash. eBay shuts down GameStop's bid. OpenAI puts $14 billion behind an enterprise AI play. The Watson Weekly is sponsored by Avalara. For ecommerce brands, tax compliance gets more complicated with every new channel, state, product, and market. Avalara Agentic Tax and Compliance helps automate the work behind...

Three retail moves worth talking about this week. Amazon is retiring the Rufus name. The shopping chatbot has hit roughly 300M users since its 2024 beta, but Amazon is folding the whole thing into Alexa and calling it "Alexa for shopping." We get into why that branding choice is risky given Alexa's history with kids accidentally ordering things and the privacy lawsuits, and what it signals about a...

Logicbroker brought back Connected Commerce this year, set up outside Central Park, because the conversations the team has been having with customers couldn't wait for the usual conference cycle. The pace of change forced the issue. Rick Watson had the opportunity to speak with Logicbroker CEO Omar Qari at the event. The dominant theme was the agentic shift, and it landed in a specific way for Log...