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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.
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.
237 Episodes
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Today on our show:ChatGPT's 4% Fee Confirms Marketplace EconomicsAmerican Eagle to Close Quiet Logistics BusinessUPS Releases 4Q 2025 Earnings and Provides 2026 GuidanceMeta Earnings in Superintelligence We Trust- 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
In this Friday edition of Watson Weekly, Rick Watson and Jessica Lesesky dive into the major shifts rocking the retail and tech landscape. From Shopify’s controversial partner strategy to Apple’s "defensive sprint" into wearable AI hardware, we break down what these moves mean for the future of the industry.On this week's episode:* The Fall of Quiet Logistics: American Eagle is sunsetting its Quiet Logistics business. Rick and Jess explore why owning your own supply chain can be a "heavy burden" if it’s not your core business.* Apple’s Ambient Ambitions: Is Apple panicking over all the OpenAI hype? Learn about the new AI pin designed to combat OpenAI, and why Apple is reportedly paying Google a billion dollars for the use of the Gemini model inside Siri.* Vinted’s American Dream: The European secondhand giant enters a crowded U.S. market. Can their buyer-fee model disrupt established players like Poshmark and The RealReal?*Shopify’s "Partner Massacre": Is Shopify abandoning the enterprise? Rick and Jess discuss the recent cuts to Shopify’s partner teams and CEO Tobi Lütke’s drive for "productivity over people".Key Takeaways:Why the "platform dream" failed for American Eagle.The difference between owning a logistics company and owning its "crown jewels".Why Shopify views anyone between them and their merchants as a "middleman".Support the Show: 🔔 Subscribe for more deep dives into retail and e-commerce news.#Ecommerce #Shopify #RetailTech #AppleAI #Logistics #Vinted #WatsonWeekly #thewatsonweekly
In this episode of The Watson Weekly, Rick Watson sits down with Gareth Cummings, CEO of eDesk, to discuss the massive shift in how brands interact with their customers. From pioneering domain-specific language models in 2018 to navigating the rise of TikTok Shop and Agentic Commerce, Gareth shares a masterclass in staying ahead of the tech curve.Gareth Cummings is the CEO of eDesk, an AI-native customer support platform built specifically for e-commerce. With a background in banking and telecom, he brings a unique, data-driven perspective to online retail.In this interview, you’ll learn:The Evolution of AI: Why customer skepticism has turned into an expectation for AI-driven support.Surviving the SaaS Slump: How e-commerce brands are pivoting toward profitability and value.TikTok & Authentic Engagement: Why new channels are essential for building brand trust in 2026.The Rise of AI Agents: What happens when AI starts making the purchases for us?Chapters / Timestamps0:00 - Introduction: Meet Gareth Cummings, CEO of eDesk2:15 - Career Evolution: From Banking and Telecom to E-commerce Tech5:40 - The Early Days of AI: Building Language Models in 20189:25 - The Shift in Consumer Mindset: From AI Skepticism to AI Expectation13:10 - Navigating the Modern SaaS Economy: Profitability vs. Growth17:35 - Building Brand Loyalty: Why Trust Outperforms Price21:50 - TikTok Shop and the Power of Authentic Engagement26:15 - Turning Support Data into a Business Strategy Engine30:40 - The Future of Agentic Commerce: When AI Does the Shopping35:20 - Leadership Advice: Embracing the Pace of AI Change38:45 - Closing Thoughts and Where to Follow GarethThe Watson Weekly is sponsored by Rithum. In commerce, timing is everything. That’s where Rithum comes in. We help brands and retailers keep every channel connected, so when the moment comes, you’re ready to act—launching faster, adapting quicker, and growing smarter.See how your business can grow at rithum.com. that's R-I-T-H-U-M.com#Ecommerce #AI #SaaS #CustomerSupport #TikTokShop #AgenticCommerce #TheWatsonWeekly #WatsonWeekly
Today on our show:Sam Altman Testing AdLowes to license its checkoutAI meets Davos and a Jassy SightingClaude Code Is Having a Viral Moment- and finally, The Investor Minute, which contains 3 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
Most AI pilots fail—at least, that’s the headline. But today’s guest is proving that doesn’t have to be true.In this Watson Weekly interview, Rick Watson goes behind the scenes with Chris Kellner, CEO of DigitalGenius, to discuss how a decade-old AI pioneer is navigating the modern LLM explosion. We move past the hype to explore how AI is actually rewriting the playbooks for sales, marketing, and customer support.In this episode, you’ll learn:* The "Locomotive" Metaphor: Why DigitalGenius didn't have to reinvent itself, but rather accelerated on existing tracks.* Sales & Marketing Rewired: How Chris’s team uses AI for call coaching, MEDPIC scorecards, and CRM automation to let humans focus on high-value closing.* UK vs. US Market Mismatch: Why traditional outbound playbooks failed when crossing the Atlantic and what they did to fix it.*The Competition for Culture: How an internal "Agent-Building" competition spurred unexpected creativity across the company.3 Hard Lessons in AI Support: The essential checklist for any leader deploying AI in customer service today.Chapters00:00 – Intro: Turning AI buzz into customer wins 03:15 – Chris Kellner’s journey from Banking to SaaS CEO 07:40 – Acceleration vs. Reinvention: Building the AI train line 14:20 – Rewiring GTM: AI call coaching and MEDPIC scorecards 22:10 – Market Mismatches: Lessons from scaling from the UK to the US 30:45 – Culture & Internal Adoption: The AI Agent competition 38:30 – Why most AI pilots fail (and how to make yours succeed) 45:15 – Build vs. Buy: When to go in-house and when to use a vendor 52:00 – Closing thoughts and key takeaways#watsonweekly #ai #customersupport
Today on our show:Walmart Shakes Up Its Leadership RanksNRF 2026 RecapMore Content Coming To You from the Watson Weekly- and finally, The Investor Minute which contains 4 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
Today on our show:It’s Time to Be Bold in 2026Welcome to NRF- 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
Today on our show it’s no news, just thank yous.It’s been a roller coaster of a year for everyone, and despite everything, you have tuned in. Walking your dog, on the way to work, even in the shower you were there. Listening, laughing, cringing, and hopefully, even learning.I started this podcast back in 2021 and look forward to doing it for many more years. The fact that our content and presence continue to grow each year is a testament to you.So, here it is. Thank you for listening. If you like what we’re doing, reach out. Tell us what you like about it, recommend it to a friend. And of course, have a Happy Holidays wherever the end of this year takes you.This is Rick Watson, signing off for the year. I also wanted to say a huge thank you to my partners in crime Hendrik, Libby, Kaylea, Jacque, Vinny and Ron, without you this podcast would not be possible.Today's episode is sponsored by Mirakl.https://www.rmwcommerce.com/ecommerce-podcast-watsonweekly
Today on our show:Shopify Winter Editions 2025 Special Podcast- 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
Today on our show:Black Friday Cyber Monday - You Devil You!Sam Altman Calls a Code Red to Stop Google ThreatAmazon and Visa Partner on Agentic PaymentsNike CEO Purges John Donahoe’s Lieutenants- and finally, The Investor Minute which contains 3 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
Today on our show:Walmart Plans a CEO TransitionCommerce Operations Foundation Critical to Our Common Agentic FutureIntuit's Announcement Makes it Clear: OpenAI Coming for Operating SystemsWalmart Earnings Call Important for Everyone to Understand- 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
Today on our show:Same-Day Facilities Key to Amazon's New Powerful Grocery StrategyWalmart CEO Doug McMillion Steps DownTheRealReal Records Record GMV During EarningsGoogle Releases Some AI Shopping Updates- 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
Today on our show:Implications of Amazon Working with OpenAI and ChatGPTShopify Reports Great Q3 EarningsSome of the Worst Mistakes I Made First Time as CEOKlaviyo’s Earnings Answer Some Key Questions- 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
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
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
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
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
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.
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
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
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