The Watson Weekly: eCommerce Strategy & News

Watson Weekly
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Stop reading the headlines and start understanding the frameworks. The Watson Weekly is the premier resource for eCommerce executives, delivering sharp, independent strategy on the industry's most critical developments. Join 20-year veteran Rick Watson as he cuts through the noise to help you understand not just what is happening, but why it matters to your business. Broadcasting three times a week: Mondays: Strategic deep dives into earnings, mergers, and market shifts. Wednesdays: Candid interviews with C-Suite luminaries and tech innovators. Fridays: Join the Watson Weekend for Spirited debates on controversial topics with co-host Jessica Lesesky. From AI implementation and marketplace dynamics to supply chain logistics and retail operations, we cover the entire commerce landscape. Whether you are a CEO, VP, or operator, this is your competitive advantage in audio form.

  1. 21h ago

    Amazon Blocks AI Shopping Agents as Oreos Climb From 10% to 70%

    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 right to keep agents out and points to Meta's record on account security as a reason to be careful about handing any agent your cards. Shopify and Walmart are going the other direction, though nobody is reporting what Walmart actually sells inside ChatGPT. They also cover who is on the hook when an agent buys something it shouldn't have, and what happens to retail media, a $170B business last year, when the shopper reading the page is a bot that never sees an ad. The back half is about Oreos. Mondelez found its cookies came up in about 10% of AI cookie recommendations, brought in AEO and GEO firms, and now shows up around 70% of the time according to the Goldman research. Rick and Jess also disagree on whether you separate the cookie before eating it. For brands that aren't showing up in agent results, part of the fix is technical work on their own sites, and some are blocking agents they don't know about. This episode is sponsored by Avalara.

  2. 2d ago

    Your Data Lake Won't Make You AI-Ready

    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 which system to trust, so the agent picks up the first answer it finds and presents it with full confidence. Ask a retailer for its customer count or gross margin and different teams will often give different numbers. People know which dashboard to believe. Agents don't. Abhi walks through what he thinks a semantic layer needs to include, and the piece he says most companies leave out, which is the history of how the data changed over time. Rick and Abhi also get into buy versus build. Abhi's view is that retailers should never build the control layer (governance, gateways, LLM monitoring, cost tracking) because it changes every time a new model ships. What retailers should own are their definitions and workflows. He thinks the big consulting firms are right to push master data cleanup and operating model work, and wrong when they spend 12 to 18 months building a bespoke agent data layer the client then has to maintain alone. On ownership, Abhi puts meaning with the business (merchandising, finance, supply chain), enforcement with technology, and a small product data team between them. By his estimate, about 5 in 100 retailers he talks to have that team in place. He also explains what happens when a marketing manager starts uploading customer CSVs to a chatbot on their own, and why the answer is governance rather than a ban. Abhi's company is built on the bet that data readiness is never finished. Weigh that accordingly. The last decade of retailers building and rebuilding their own checkouts suggests he has a point. This episode is sponsored by EKYAM. #AIAgents #Retail #Ecommerce

  3. Sep 25

    Amazon Wants to Handle Agent Payments While Blocking Agents

    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 from the places where it doesn't, and Rick says the startup alley has been the strongest part of the show. The booth he keeps coming back to belongs to Amazon. It used to be the Amazon payments booth. This year it's Amazon agentic payments, and the only change Rick can find is the added word. He has trouble with the idea that retailers should hand their agent payment strategy to a company he describes as blocking agents all over the internet. #watsonweekly #amazon #agenticcommerce #retailtech #ecommerce #aipayments #retailclub

  4. Sep 23

    Hairstory Collected Tax It Never Remitted, Then Fixed It

    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 largely to cofounder Erica Halliwell, who had taken on sales tax with no background in it and says it left her in tears at least once. Erica and Katie Overdevest, who runs Hairstory's ecommerce, tell Rick how the company got current and what that made possible. A cold call from DHL about its delivered-duty-paid service let Hairstory ship abroad from its one US 3PL without registering for VAT or GST in other countries, and Erica credits Avalara with calculating VAT and other local taxes in each new market. Later the company set up entities in Europe and Australia with local banking and fulfillment, moved to Shopify in 2023, and cut five websites down to one. Katie and Erica also talk through why Brazil and China are harder to enter and what consolidating subscription vendors meant for tax calculation and fixed local pricing. Erica says Avalara's managed filing still needs more manual work in Europe than in North America, and that her finance team, which is her and one bookkeeper, closes the books within ten business days. This episode is sponsored by Avalara. Learn more at avalara.watsonweekly.com. #watsonweekly #ecommerce #salestax #avalara #shopify #dtc #crossborder

  5. Sep 21

    Amazon's First Price Rate Went From 4% to Nearly 80%

    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 the inflation-adjusted price advertisers actually paid held flat. Both figures are Amazon's own. A 50% drop in winning bids should show up in what advertisers pay, and it did not. Amazon's internal documents call the mechanism a soft reserve, a floor applied after the bidding closes. Its own pricing page told advertisers they were in a second price auction where the winner pays a penny more than the runner-up and nothing beyond that. Under a soft reserve the winner pays their own bid. Amazon tracks how often that happens in a metric called first price rate, which sat at 4% in late 2020 and appears at close to 80% in the internal operating plan for 2024. Amazon says reserve prices kept placements priced at what they are genuinely worth. The FTC says the floor was set at whatever Amazon could collect without advertisers noticing. Also this week, Target's ad business and marketplace now report to a marketer who came out of hotels, and BigCommerce's parent is planning cost cuts worth a fifth of its revenue. PayPal is running its turnaround with two interim bosses. The Investor Minute carries five items from venture, M&A and the IPO market. This episode is sponsored by Avalara, which says its Agentic Tax and Compliance product automates tax calculation and gives sellers visibility into tariffs and duties across Shopify, BigCommerce and WooCommerce. Details at avalara.watsonweekly.com.

  6. Sep 18

    Amazon Isn't Your Friend. The FTC Says It Overcharged Sellers $20B

    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-style blog post, why Chair Andrew Ferguson picked this fight in a midterm year, and what Amazon's struggle to grow CPCs means for the fees and ad formats sellers will see next, including sponsored prompts. Sponsored by Avalara: avalara.watsonweekly.com Get the free Watson Weekly newsletter: https://www.watsonweekly.com

  7. Sep 16

    How to Buy AI Agents Without Getting Stuck on One Model

    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 Orium and president of the MACH Alliance, and Anatolii Iakimets, director of product marketing at KIBO. Shawn has lived through cloud, mobile, big data and the first round of enterprise AI, and he thinks the old playbook still holds. You start with the business outcome and work backward. The speed is new. So is the position a lot of mid-sized companies are in, making these calls with small engineering teams. His argument is that a lean shop has to choose its first use case carefully, because that use case ends up funding the infrastructure everything after it depends on. Jason says people are the slow part, and rethinking processes takes years, well past any single model release. He would rather see a company running five agents on safe, permissioned access to its systems and data than one running hundreds without it. Anatolii sat across the table from Shawn a decade ago selling big data. His advice to buyers is to show up knowing the exact prompts and roles they want automated, then press vendors hard on permissions and audit logs. The panel also gets into model lock-in and why narrowly scoped agents tend to succeed where big general-purpose builds stall. Shawn points out the category is roughly ten months old. When Rick asked what good looks like, his first answer was that maybe nobody knows yet. #AgenticAI #MACHAlliance #EnterpriseAI #KIBO #WatsonWeekly

  8. Sep 15

    Costco Said Next Was Growing, Then Deleted It Over a Weekend

    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 guidance. Rick's read is that a retailer winning because the economy is bad has borrowed the quarter and pays it back later. The more durable move is the $1 frozen set sitting on top of DG Fresh, because a dollar store with a working cold chain is a grocery store in places that don't have one. Costco shut down the Costco Next marketplace at the end of August, over a weekend, with no notice. Members who bought through it can no longer return the item to Costco. Customer service hands them a vendor phone number. The last thing Costco said publicly about Next was on the third quarter call last May, when CFO Gary Millerchip said a single quarter's sales matched the program's entire fiscal 2022. There has never been a dollar figure for Next in any filing, and a growth rate without a denominator is what you hand analysts when the absolute number is small. Fourth quarter and full year results land September 24. Greg Foran is rebuilding Kroger with the people he ran Walmart US with. Nate Faber, who cofounded Jet.com and ran supply chain for Walmart's US eCommerce, started as eCommerce chief September 1. Mark Ibbotson, formerly central operations at Walmart and COO at Asda, starts in stores today. Earnings landed between the two start dates. eCommerce grew 20% and turned a profit for a second straight quarter. Identical sales excluding fuel grew two tenths of 1%, and the full year outlook for that measure got cut. Foran called the price work a glide path funded by cost savings rather than margin, which raises the question of what actually pays for it when almost all of roughly $147 billion in revenue is food, operating profit is a little over 3 cents on the dollar, and more than 400,000 associates work under UFCW contracts. Anthropic published a commerce agent blueprint on September 2, a public GitHub repo with two working reference builds, one shopping agent and one merchant agent. The company says retailers running these see carts up to 35% larger and shoppers 60% more likely to complete a purchase. Those numbers come from the vendor giving the code away, with no baseline and no outside auditor. The blueprint is also silent on payment. Visa and Mastercard are quoted in the announcement talking about trust, and neither shipped code. Shopify's Vanessa Lee says they're building a reference storefront connecting the blueprint through catalog, the universal commerce protocol, and Shop sign-in, which puts Shopify's own login layer inside someone else's agent framework. Somebody could run this in production before December and find out what a 35% lift looks like when it's measured by a party that didn't build it. Plus the Investor Minute with four raises: Locus Robotics Series G, Atorie in seed, Advizar pre-seed, and Overroute in seed. The Watson Weekly podcast is sponsored by Avalara. Learn more at: avalara.watsonweekly.com #watsonweekly #dollartree #costco #kroger #anthropic #ecommerce

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Stop reading the headlines and start understanding the frameworks. The Watson Weekly is the premier resource for eCommerce executives, delivering sharp, independent strategy on the industry's most critical developments. Join 20-year veteran Rick Watson as he cuts through the noise to help you understand not just what is happening, but why it matters to your business. Broadcasting three times a week: Mondays: Strategic deep dives into earnings, mergers, and market shifts. Wednesdays: Candid interviews with C-Suite luminaries and tech innovators. Fridays: Join the Watson Weekend for Spirited debates on controversial topics with co-host Jessica Lesesky. From AI implementation and marketplace dynamics to supply chain logistics and retail operations, we cover the entire commerce landscape. Whether you are a CEO, VP, or operator, this is your competitive advantage in audio form.

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