The Watson Weekly: eCommerce Strategy & News March 9th, 2026: Shopify Middleware? Stripe Letter, Amazon-OpenAI Deal, & Thoma Bravo
The AI shopping revolution is here ā but who actually controls it? In this week's Watson Weekly, Rick Watson breaks down four stories reshaping the future of e-commerce.
The Watson Weekly is sponsored by Avalara. For more information on Avalara visit - https://www.avalara.watsonweekly.com/
š Shopify vs. AI Agents ā Shopify is making a bold bet: positioning itself as the back office of record for the agentic web. But if LLMs keep getting smarter, does the middleware even survive? Rick walks through two scenarios that every e-commerce operator needs to understand.
š³ The Stripe Annual Letter ā $1.9 trillion in payment volume, a "stablecoin summer," and a controversial vision for Level 5 agentic commerce (AI that buys things before you ask). Is this a consumer-friendly future or a payments provider's dream dressed up as progress?
The Watson Weekly is also sponsored by Mirakl. You don't need another tool; you need a growth partner. The Mirakl platform is powering the next era of retail for brands and retailers who are ready to move, powered by AI and built for what's next.
š¤ The Amazon-OpenAI $50B Deal ā What it means for AWS, Nvidia, and Alexa ā and the one glaring thing that's missing from the deal that tells you everything about how these negotiations really work.
š The Logistics Rollup ā Thoma Bravo is merging Auctane (ShipStation, Stamps.com, Metapack) with WWEX Group to build an end-to-end logistics intelligence stack. Could this be the most important supply chain bet of the decade?
Plus: this week's Investor Minute covers Salesforce's acquisition of Momentum, Aritzia's buy of Fred Segal, and two fresh seed rounds in supply chain tech.
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