The Watson Weekly: eCommerce Strategy & News

Anthropic has filed its S-1, and Rick Watson and Jessica Lesesky use the filing to ask whether software companies are in real trouble. Reported targets put the raise at $100 billion or more at a valuation of up to $2 trillion, which would top SpaceX. OpenAI, meanwhile, has pushed back its IPO and is reportedly raising $30 billion privately at about $1.4 trillion. Jess goes back to the software sel...

I asked the retailers and brands at Retail Club to raise a hand. About ten or eleven went up. When I asked who had good data, one hand stayed. This was our first Watson Live! The Retail AI Debates at RetailClub Presented by KIBO Commerce. Speakers argued assigned sides, some they don’t personally hold, and the room voted with red and blue plates after each round. Debate one asked whether retailers...

Salesforce agreed to pay about $5.7 billion in cash for Braze, the software brands like Instacart and Urban Outfitters use to send push notifications and texts. Rick works out what that comes to per customer. Salesforce hasn’t said how it will sell Braze alongside Marketing Cloud, the product a lot of Braze customers left to get there. ChatGPT referral traffic dropped out of analytics reports for...

Shopify has bought shop.com from Market America and won’t say what it paid. Rick Watson and Jessica Lesesky use the deal to work out where Shopify fits once AI agents do more of the shopping. Rick thinks Shop Pay matters most. If agents skip the storefront, Shopify may be left owning the checkout and not much else, and he thinks that could still be a very good business. Jess sees Shopify going aft...

PartsTree has sold replacement parts for lawnmowers and other outdoor power equipment for about 20 years, mostly on software its own team built. By this year the code had become something nobody wanted to touch. Some of it was written more than 20 years ago, and only one person could fix it when it broke. Vinny O’Brien sat down with Doug and Drew from PartsTree and Chris from Altus Nova at Shoptob...

Vinny O’Brien says e-commerce conversion rates have hovered around 3% for twenty years. He puts that to Darin Lynch at Shoptoberfest, and Darin’s answer is that a lot of B2B companies are measuring success in the wrong place. Darin started Irish Titan 22 years ago. He sorts commerce history into rough eras. He calls the early one Neanderthal commerce, when sites were difficult for merchants to bui...

UPS has now shed almost all of its Amazon volume. The 18-month wind-down took out about two million pieces a day and roughly $4.5 billion in expenses, leaving UPS with a smaller network that earns more per package but has less volume to set prices with. Rick looks at who held the leverage in that split, and whether a UPS focused on healthcare logistics is turning into a specialty carrier. BJ’s Who...

Rick thinks Starbucks has lost its way. Jess thinks Brian Niccol’s turnaround is working, and she points to four straight quarters of growth. Niccol has put handwritten Sharpie names back on cups and is spending $1.2 billion to make stores more comfortable. Rick says a better seat means nothing when you wait 25 minutes for burnt coffee. Jess says consistency matters more than quality, and that cak...

Keith Pires is CRO and co-founder of Boldest, an agency built on top of an agent platform called Pathfinder. Vinny O’Brien caught up with him at Shoptoberfest in Nashville, shortly after both of them came off the mechanical bull. Pires says his co-founder and CTO, Ramy Youssef, has been developing Pathfinder for many years with a team based in Egypt. He describes it as the foundation of the agency...

Naturepedic has made organic mattresses for years. Its three owners are engineers, and the marketing used to read like their spec sheets. Arin Schultz, the chief growth officer, changed the messaging before anyone approved it. He says sales were up 46% in May and close to 68% in July, and he puts the mattress category down by double digits over the same period. Arin runs sales and marketing as one...

C.H. Robinson is paying $5.8 billion in cash and stock for RXO, which Rick works out to more than 40 times RXO’s expected adjusted EBITDA for this year. The deal deck brings that down to about 13 times, but only by counting $300 million in cost savings that haven’t happened yet. Retail and e-commerce make up 37% of RXO’s revenue. Also this week, ChatGPT adds virtual try-on to its shopping results,...

Costco’s sales rose 11.2% last quarter, and Rick Watson and Jessica Lesesky talk through where that growth is coming from. Costco says members under 40 now make up more than a quarter of the base. Many of them live in apartments and order on their phones, and Costco says delivery orders arrive in under an hour on average. Rick joined recently and bought a mattress there. Jess isn’t a member becaus...

Tom McFadyen has spent decades building marketplaces and commerce platforms at McFadyen Digital. His firm's new book, AI Best Practices for Commerce, runs more than 500 pages in print, and Tom says the printed version couldn't keep pace with how fast the material changed. I caught up with Tom at Retail Club. The book launched with 125 AI use cases, sorted into four phases of commerce that McFadyen...

Amazon now lets US sellers run their eBay, Shopify, TikTok and Walmart sales inside Seller Central, free of charge. Amazon says more than 95% of its independent sellers already sell elsewhere, and each of those outside orders now sits next to an Amazon shipping button. Rick Watson thinks most sellers will be reluctant to put their Walmart numbers inside Amazon's software. Oura postponed its NASDAQ...

Amazon is blocking nearly every AI shopping agent, starting with Perplexity. Rick Watson and Jessica Lesesky go through Goldman Sachs' 64-page report on agentic commerce, which opens on Amazon's blocking and includes a section on agent liability that is labeled TBD. Rick reads the blocking as a negotiating position, the same move Amazon made with Buy With Prime and Shopify. Jess thinks Amazon is r...

Every retailer wants AI agents, and very few have data an agent can use. Abhi Sachdeva, co-founder and CTO of EKYAM, has spent 18 of his 24 years in technology inside retail, running tech at 1-800-Flowers, Tory Burch and QVC. He joins Rick to explain what data readiness requires and where retailers keep getting it wrong. A data lake stores rows. It doesn't tell an agent what those rows mean or whi...

Rick Watson reports from the Retail Club AI event in Huntington Beach, which he's calling the source of the agentic fog he first described at Shoptalk. This is the second stop in the on-location series that started there. It's hot, there isn't much shade, and lunch is small portions from a handful of food trucks. The talks are better. More presenters are now separating the places where AI fits fro...

Hairstory launched at the end of 2015 selling online to consumers and hairdressers across the US. It collected sales tax from launch but registered in only a handful of states, so for about a year the tax it owed everywhere else sat in a separate bank account and kept growing. Catching up, even with Avalara's help, took months of pulling order-level data for each state's forms, work that fell larg...

The FTC says Amazon ran an ad auction, got an answer, then replaced it with a higher price it set itself. The complaint landed in Seattle on August 31 with 22 state attorneys general attached and runs 181 pages. The agency puts the money involved above $20 billion. Amazon answered the next day with a blog post. Average winning bids on its search ads fell 50% between 2019 and 2025, it said, while t...

The FTC and 22 state attorneys general are suing Amazon over its ad auctions. They say an undisclosed soft reserve pushed up what 1.2 million advertisers paid and cost them more than $20 billion since 2019. Amazon says CPCs stayed flat after inflation, conversion went up, and nobody was harmed. Rick Watson and Jessica Lesesky go through the complaint, Amazon's same-day rebuttal and its Genesis-sty...

Every CIO has been told to invest in agentic AI. Nobody has told them how much to spend or when. Shawn Mandel is working through that decision right now as CTO of Dentalcorp, which supports more than 650 dental practices across Canada and, since July, the US. He joins Rick Watson for a Watson Weekly webinar on technology decisions in the agentic era, alongside Jason Cottrell, founder and CEO of Or...

Dollar Tree's everyday basics grew almost 6% last quarter. The discretionary side, toys and seasonal and party goods, grew under 2%. Dollar Tree and Dollar General reported the same day, and both chief executives worked hard to tell analysts the spread doesn't mean what you think it means. Dollar General credits its share gains to households making over $100,000 a year and raised full year guidanc...

Anthropic has moved into commerce. On September 2 it put an open-source blueprint on GitHub for building a shopping agent and a merchant agent on Claude, with demo builds for retail, travel, telecom and ticketing. Rick Watson and Jessica Lesesky have about 50 years of e-commerce experience between them. By their count, the co-authors behind Anthropic's commerce memos add up to roughly four. Anthro...

Andy Hoar thinks the industry is fighting over the wrong ground. The storefront and the last mile get the budget because those are the parts a customer can see. Andy's case is that in B2B the money sits in the middle miles, the stretch between the click and the dock where pricing gets calculated, inventory gets allocated and orders get tracked. Bots are already good at that work, in part because t...

Retail's second quarter doesn't compare to anything, and the reason is a refund. In February the Supreme Court ruled that the emergency powers law behind the White House tariffs never granted the authority to impose them. Importers of record filed to get the money back and it landed in Q2. Walmart was eligible for roughly $2.9 billion. Home Depot took $730 million. Target booked a $994 million pre...