

The Watson Weekly: eCommerce Strategy & News
Watson Weekly
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.
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.
Episodes
Mentioned books

Nov 3, 2025 • 14min
November 3rd, 2025: Walmart Holiday Plans Shows There Will Be Blood, UPS Gains Margin, Plans Strong Peak, But Remains Mired in Uncertainty, Amazon All In On Agentic - Reports Great Earnings, and Shopify Merchants Go Live with ChatGPT Instant Checkout
Today on our show:Walmart Holiday Plans Shows There Will Be BloodUPS Gains Margin, Plans Strong Peak, But Remains Mired in UncertaintyAmazon All In On Agentic - Reports Great EarningsShopify Merchants Go Live with ChatGPT Instant Checkout- and finally, The Investor Minute which contains 5 items this week from the world of venture capital, acquisitions, and IPOs.Today's episode is sponsored by Rithum.https://www.rmwcommerce.com/ecommerce-podcast-watsonweekly

Oct 27, 2025 • 14min
October 27th, 2025: Commercetools CEO is out, so what’s next? Bigcommerce partners with Paypal to improve monetization, Will the new Ulta Beauty marketplace cook? And Shopify and Lovable Integration Shows a Fire and Motion Strategy
Today on our show:Commercetools CEO is out, so what’s next?Bigcommerce partners with Paypal to improve monetizationWill the new Ulta Beauty marketplace cook?Shopify and Lovable Integration Shows a Fire and Motion Strategy- and finally, The Investor Minute which contains 5 items this week from the world of venture capital, acquisitions, and IPOs.Today's episode is sponsored by Mirakl.https://www.rmwcommerce.com/ecommerce-podcast-watsonweekly

Oct 20, 2025 • 10min
October 20th, 2025: Walmart Partners With OpenAI, Cannot Hold Back the Tide, S&P Global Puts Tariff Costs at $1.2T This Year, Salesforce Partners With OpenAI, and Saks Struggles to Deliver in Q2
Today on our show:Walmart Partners With OpenAI, Cannot Hold Back the TideS&P Global Puts Tariff Costs at $1.2T This YearSalesforce Partners With OpenAISaks Struggles to Deliver in Q2- and finally, The Investor Minute which contains 5 items this week from the world of venture capital, acquisitions, and IPOs.Today's episode is sponsored by Mirakl.https://www.rmwcommerce.com/ecommerce-podcast-watsonweekly

Oct 13, 2025 • 15min
October 13th, 2025: Process Re-Engineering Is a Key Skill in the Age of AI, Stripe Link Moving More Consumer Facing, Is OpenAI Building a Super App? And Shopify CRO Bobby Morrison Forced Out
Today on our show:Process Re-Engineering Is a Key Skill in the Age of AIStripe Link Moving More Consumer FacingIs OpenAI Building a Super App?Shopify CRO Bobby Morrison Forced Out- and finally, The Investor Minute which contains 5 items this week from the world of venture capital, acquisitions, and IPOs.Today's episode is sponsored by Mirakl.https://www.rmwcommerce.com/ecommerce-podcast-watsonweekly

Oct 9, 2025 • 32min
The CEO Spot with Matt Harris of Harris Digital
In this second episode of The CEO Spot, Rick Watson sits down with Matt Harris, Founder of Harris Digital. The interviews were conducted at Shoptoberfest 2025, discussing the state of B2B e-commerce and the challenges of 'hard commerce' faced by manufacturers and distributors.Harris explains that many companies struggle with legacy ERP systems, analog data management, and complex pricing models involving tiered and customer-specific discounts. He emphasizes the importance of product information management (PIM) systems in cleaning and centralizing data before launching e-commerce platforms. Harris shares his background, starting in the 1990s, with early e-commerce projects and how his agency helps mid-market manufacturers (with up to $1 billion in revenue) modernize sales by augmenting—not replacing—existing ERP systems. He discusses the friction caused by generational mindset shifts and private equity consolidation in these industries. On AI, Harris notes that while small-scale AI and analytics are useful, most enterprise AI projects fail to deliver revenue due to siloed data and unrealistic expectations; he advocates for building unified data lakes and warehouses as a foundation for future AI-driven business improvements.

Oct 6, 2025 • 12min
October 6th, 2025: ChatGPT Is Actually The Ultimate In Influencer-Driven Commerce and OpenAI x Stripe Agentic Commerce Protocol Has Makings of Silicon Valley Catfight
Today on our show:ChatGPT Is Actually The Ultimate In Influencer-Driven CommerceOpenAI x Stripe Agentic Commerce Protocol Has Makings of Silicon Valley Catfight- and finally, The Investor Minute which contains 5 items this week from the world of venture capital, acquisitions, and IPOs.Today's episode is sponsored by Mirakl.https://www.rmwcommerce.com/ecommerce-podcast-watsonweekly

Sep 29, 2025 • 13min
September 29th, 2025: What the Hell Will Happen At Tiktok? Ryder Releases New eCommerce Study, Klaviyo Innovations Made Possible By Different Ecosystem Approach, and OpenAI Announces They Are Pursuing Ads
Today on our show:What the Hell Will Happen At Tiktok?Ryder Releases New eCommerce StudyKlaviyo Innovations Made Possible By Different Ecosystem ApproachOpenAI Announces They Are Pursuing Ads- and finally, The Investor Minute which contains 5 items this week from the world of venture capital, acquisitions, and IPOs.Today's episode is sponsored by Rithum.https://www.rmwcommerce.com/ecommerce-podcast-watsonweekly

Sep 22, 2025 • 12min
September 22nd, 2025: Google and Paypal Announce New Commerce Partnership, Fireside Chat With Andy Jassy at Amazon Accelerate Conference, and The First Q4 Holiday Predictions Appear
Today on our show:Google and Paypal Announce New Commerce PartnershipFireside Chat With Andy Jassy at Amazon Accelerate ConferenceThe First Q4 Holiday Predictions Appear- and finally, The Investor Minute which contains 5 items this week from the world of venture capital, acquisitions, and IPOs.Today's episode is sponsored by Rithum.https://www.rmwcommerce.com/ecommerce-podcast-watsonweekly

Sep 15, 2025 • 26min
September 15th, 2025: The Future is Less If Then And More Prompts, Agents, and MCP - A SVP Looks to the Future
We have a special episode of the podcast this week. Today we preview a new podcast from RMW Commerce — actually a Youtube Exclusive, called “Oh Shift! Where SaaS Meets AI”.In this week’s episode, I interview the Shailesh Kumar, the SVP Of Engineering at Salesforce Commrece Cloud to talk about the company’s approach and pilots in the world of AI and Model Context Protocol or MCP. To be clear, this is not any kind of sponsored interview. It’s just an exploration of how the platforms - and I have asked them all to come on the program - are approaching AI and MCP, and what implications it has for brand and merchants.Today's episode is sponsored by Rithum.https://www.rmwcommerce.com/ecommerce-podcast-watsonweekly

Sep 8, 2025 • 15min
September 8th, 2025: Shopify Betting Big on Design, Amazon Still Stuck Muddling Through Day 2, Why Software Sales Is Still Hard in 2025, A New Podcast where SaaS Meets AI: Oh Shift
Today on our show:Shopify Betting Big on DesignAmazon Still Stuck Muddling Through Day 2Why Software Sales Is Still Hard in 2025A New Podcast where SaaS Meets AI: Oh Shift- and finally, The Investor Minute which contains 5 items this week from the world of venture capital, acquisitions, and IPOs.Today's episode is sponsored by Mirakl.https://www.rmwcommerce.com/ecommerce-podcast-watsonweekly


