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. 3d ago

    Why DIY Retail Chatbots Break After the Demo

    Most shoppers don’t want to talk to a chatbot. Zoovu CEO Jonathan Taylor says the ones who do convert at a higher rate. He argues retailers have to serve both groups, and a chatbot that wins over one group by driving off the other hasn’t gained anything. Taylor took over at Zoovu in January and joined Rick Watson in the Watson Weekly Manhattan studio. He says about half of Zoovu’s business is B2B, including fire suppression valves and breathing apparatus for firefighters. In that work a bad answer is a safety problem. It pushed the company to get its product data right long before chat was common on retail sites. Rick and Jonathan get into self-built bots that demo well and then say wrong things to real customers. Taylor says you can now get a chatbot 70% of the way there in an afternoon. Prompt injection protection and PII handling come after that, and he says the real cost shows up in years two and three. On measurement, Rick compares chat counts to the impression numbers retailers chased in the early 2000s. Taylor wants retailers to split their traffic into cohorts and track total conversion across the site. He describes one B2B customer that tested conversational search on its own sales and support reps before buyers ever saw it. Taylor is less convinced by agentic shopping. He thinks people want help finding their next laptop and would still rather choose it themselves, which leaves open what retail agents will actually be used for. This episode is in partnership with Zoovu.

  2. 5d ago

    Amazon Ads Slow to 11%, FedEx Raises Outlook, Shopify’s AI Orders, Walmart’s $6B Robot Bet, Klaviyo Beats Guidance

    Amazon’s ad business grew 11% to $19.6 billion last quarter. Media reports called it Amazon’s first ad miss in seven quarters. Amazon says moving Prime Day into June took 8.5 points off third-quarter ad growth. Rick compared that claim with the six-month numbers and mostly accepts it. He is less comfortable with the fourth-quarter guide of high-teens ad growth, which is still below the 22% to 23% Amazon posted a year ago. AWS grew 39% to $46 billion, and by Rick’s math it produced 63% of Amazon’s operating income. FedEx raised its 2026 profit outlook on 2% domestic volume growth and 7% higher revenue per package. Parcel rates go up another 5.9% on January 4. Shopify processed $119 billion in merchant sales and says orders from AI channels grew 3.3 times, without giving a base number. Its CFO said about 1.5 points of the four-point free cash flow margin gain are structural and the rest is temporary. Walmart committed about $6 billion more to Symbotic warehouse robots across 25 regional distribution centers. The two companies first agreed in 2022 to put Symbotic in all 42 of Walmart’s regional DCs. Klaviyo beat its own revenue and profit guidance, raised its full-year outlook and launched Klaviyo Headless, which lets AI assistants like ChatGPT and Claude pull Klaviyo data. Rick is hosting a live event at NRF 2027 on Saturday, January 9, in New York City. Register your interest at watsonweekly.com/events. #watsonweekly #amazon #shopify #walmart #fedex #klaviyo

  3. Nov 6

    AWS Grew 39% and Jassy Now Sees Two Trillion-Dollar Businesses Within 10 Years

    Andy Jassy told investors and analysts that Amazon may have two trillion-dollar revenue businesses within five to 10 years, though it doesn’t have one yet. Rick Watson and Jessica Lesesky run the numbers on both. AWS grew 39% to $46 billion in Q3 2026, and Jassy says it can grow more than 40% in each of 2027 and 2028. If that holds, AWS gets close to a trillion around 2031. The retail side takes more work to get there. Jess walks through the Watson Weekly napkin Math to a trillion-dollar stores business by 2036, where Amazon’s existing businesses cover most of the distance and grocery has to add about $45 billion. If seller fees and ads keep slowing, grocery needs another $15 to $20 billion on top of that, and Amazon would have to compete with Walmart and Costco to be the country’s top grocer. Rick and Jess also discuss why Amazon says it will work with horizontal shopping agents but won’t pay for placement, and Rick tries to square Jassy’s new AWS flywheel with a data center power gap that neither party seems keen to close. Jess introduces her shopping agent, Didle. Subscribe to the newsletter at watsonweekly.com. #watsonweekly #amazon #aws #grocery #walmart #alexa #ecommerce #agenticcommerce

  4. Nov 4

    Retailers Say Under 5% by 2027. Shopware’s Co-Founder Says 30% by 2030

    Shopware co-founder Stefan Hamann thinks about 30% of buying will be in the hands of agents by 2030, and probably more in B2B than B2C. Rick opens with a state of the union drawn from six months on the road, including an NRF combined councils meeting of CIOs and chief digital officers. Today agentic commerce mostly means discovery: whether an agent finds your product in the first place. Rick sorts retailers into four buckets (watchers, foundation fixers, pilots and deployed) and explains why about three in four of the NRF council members won’t let AI generate creative for brand-critical imagery. Stefan Hamann, now Shopware’s Chief Agentic Officer, explains why he started the Agentic Commerce Alliance and how its free readiness scanner works. He also suggests an exercise every merchant should run: ask your own staff for every reason a customer should not buy a product. An agent usually shows a shopper about three options, so it needs to know what your product is bad at. He thinks an agent that buys on your behalf is months away, not years. Then four agency and merchant pairs show what the work looks like: Keith Pires of Boldest and Lori Lash Valencia of The Mall Street on a New York premium marketplace with no sponsored placements, no private label, and brands that get their customer data. Chris Hedge of Altus Nova and Zach Frost of Peak Capital on moving PartsTree off a 25-year-old custom platform. That meant 450,000 models, more than 4 million parts and 150-plus OEM data feeds, with AI used to check every migrated record.Darin Lynch of Irish Titan and Sean White of ElleVet Sciences on running two audiences across three sites, launching wholesale for vets first, and moving pet supplement subscriptions to a new platform with no customer re-entering a card.Jonathan Tenpenny of AmericanEagle.com and Eric Nettleton of SANY America on dealer-branded catalogs for heavy equipment. Most of these projects are foundation work, and Rick argues that’s the right order. Sponsored by Shopware Agentic Commerce Alliance: https://www.agentic-commerce.org/ Agentic Readiness Scanner: https://agenticcommerce.shop Agentic Commerce Maturity Index: https://acmi.agentic-commerce.org/

  5. Nov 2

    DoorDash Buys Instacart, Anthropic Files to Go Public, and PayPal, UPS Earnings, and $300B in PE Debt

    DoorDash agreed on October 29 to buy Instacart for $65 a share, about $17 billion in equity value. It promised grocers they can keep using any delivery platform. Rick thinks grocers should still worry. Instacart built their websites and apps, and it’s going to a company that runs its own DashMart stores. The promise doesn’t say who gets the shopper data. PayPal processed 6% more payment volume in the third quarter and grew revenue 2%. Rick sees Venmo as the business with momentum and PayPal as the drag on it, and he names Stripe, Shopify, Amazon and Google as owners that could do more with it. UPS charged 6.1% more per US package while daily volume fell about 3%. Most of that price increase went to cost, which rose 5.5% per package. Carol Tomé told Reuters the logistics opportunity tied to data centers is worth $15 billion a year. RFID now moves 1.9 million packages a day with no hand scan, which matters with the Teamsters contract up in 2028. Anthropic filed its S-1 to list on Nasdaq as ANT, with $16.3 billion in revenue for the first half of 2026. Rick’s view is that companies now build the software they used to buy, and that the mid-tier tools are the most exposed. CRM and ERP should hold up better. The Wall Street Journal counts about $300 billion in risky loans to private equity backed companies coming due in 2028 and 2029, about a third of it in software. If a PE-owned vendor wants you on a multi-year contract this quarter, ask them about it. WatsonLIVE at NRF 2027 is Saturday, January 9 in New York. This year it’s about brands in the middle of a turnaround. Register your interest at watsonweekly.com/events. #doordash #instacart #paypal #ups #anthropic #watsonweekly

  6. Oct 30

    Anthropic Files to Go Public at Up to $2 Trillion. Is Software Doomed?

    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 selloff earlier this year, when investors decided Claude Code and Cowork would kill SaaS, a prediction that hasn’t come true yet. Rick thinks the old buy, build or partner decision now comes down to build, because marketing teams believe they can vibe code their own tools. Jess expects systems of record like NetSuite and Salesforce to hold up and worries more about the small and mid-tier apps someone could rebuild overnight. They also get into what a moat means when code is cheap, and a website that lets prospects check whether your product is just a markdown file. The IPO race splits them. Rick says OpenAI is making a mistake by waiting while Dario Amodei takes Anthropic public. Jess thinks Sam Altman is playing it like Apple, letting someone else go first and arriving later with something better. Subscribe to the newsletter at watsonweekly.com. #watsonweekly #anthropic #openai #saas #claude #ipo #ecommerce

  7. Oct 28

    Retailers Admit Their Data is Bad, Then Vote to Start AI Anyway

    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 should rebuild workflows around AI before their data is ready. Gireesh Sahukar took the yes side and won the vote. His point was that chasing clean data first never ends, and that bad inventory data starts with someone scanning blueberry yogurt instead of strawberry. Kelly Goetsch of Pipe17 argued against, partly from conviction, and pointed to Target at one point running seven master systems of record for inventory. Casey Golden of CI&T and Kevin Reese took on whether companies will regret AI-driven layoffs. Casey said retail never wrote down what anyone actually does, so cutting people removes the context AI would need. She used Dollar General pulling back on self-checkout as an automation regret that had nothing to do with AI. Kevin won the room by arguing that companies will regret how they ran layoffs much more than the decision to make them. For the third debate I stepped in against Danny Smith, who leads agentic commerce at Stripe and worked on Rufus at Amazon. I argued retailers should build their own agents first because it forces you to connect inventory, product data, service and delivery dates, and I don’t think you should hand that data to Sam Altman. Danny’s case was that shoppers want one agent that knows them across every store, so money spent on a branded chatbot nobody visits is wasted. I won the vote, and Danny had already said I would because I was the host. We closed with Anatoli Iakimets from KIBO Commerce, who argued for starting now with a vendor and keeping the budget small until the technology settles. This Watson Live event was presented by KIBO Commerce, and supported by Power Digital and Ekyam AI. Most of the room admitted their data is a mess and still voted to start. I don’t know yet whether that was the right call for retailers whose inventory counts are already wrong.

  8. Oct 26

    Salesforce Buys Braze, Walmart Bundles Sam’s Club, Amazon Drops Grocery Storefronts

    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 about a week in October. Profound traced the missing tracking tags to ChatGPT’s new Intelligent UI. The visits still arrived but were counted as direct traffic until the tags came back on October 16. Walmart now sells Walmart+ and Sam’s Club+ together for about $120 a year, $19 less than Prime. Rick thinks it’s aimed more at Costco than Amazon. Google’s universal cart is rolling out in Search and the Gemini app, with Nike, Sephora, Target and Walmart on board. Google has tried shopping checkout before and shut down Buy on Google in 2023. It hasn’t said what retailers pay. Amazon is closing the storefronts it ran on amazon.com for Winn-Dixie, Metropolitan Market, Weis Markets and Morrisons. It wants those grocers to host Amazon lockers in their stores instead. #Ecommerce #Retail #MarTech #RetailMedia #AgenticCommerce

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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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