The Watson Weekend Festive Jeoparty is a special holiday podcast episode featuring a Jeopardy-style quiz among four e-commerce and retail podcast teams: Team NYC (Rick Watson and Nick Kaplan), Retail Razor (Ricardo Belmar), Future Commerce (Philip Jackson and Brian Lange), and OGs Scott Wingo and Jason Goldberg.

The game involves answering questions about retail trends, e-commerce, industry buzzwords such as agentic commerce, BNPL, retail media networks, and consumer behavior in 2025.

Jessica Lesesky moderates the chaotic but fun competition, with rules including buzzing in and timed answers.

Throughout the game, participants discuss key retail events and trends of 2025, such as consumers' unexpected resilience amid economic concerns, the plateauing of e-commerce growth, and the evolving role of commerce in culture.

The episode ends with reflections from the participants on 2025 as a transformative year in retail, the announcement of the winners (Scott and Jason), and an invitation to join Rick Watson at the upcoming NRF event. The show closes with a festive dance party.

Chapters

Introduction of the Watson Weekend show - 0:00

Introducing the podcast teams - 2:21

Festive Jeoparty quiz - 6:40

Festive dance party - 43:23

Live taping of the Watson Weekend show at NRF 2026.

Watson Weekend Live at NRF 2026, Presented by Radial

Sunday, January 11, 2026

4:00 PM – 8:00 PM

Asylum NYC

RSVP here: https://www.rmwcommerce.com/nrf-2026

The Watson Weekend is sponsored by Mirakl.

“In commerce, you don’t need another tool. You need a growth partner. The Mirakl platform is powering the next era of retail for the brands and retailers ready to move. Powered by AI and built for what’s next."

#watsonweekend #festiveseason #jeoparty #ecommerce #retail

In this special episode of the Watson Weekend, Rick Watson is joined by Scott Silverman, Co-founder of CommerceNext and Principal of Scott Silverman Associates, to talk about e-commerce leadership themes he is seeing.

E-commerce leadership is being structurally devalued

Senior digital and e-commerce leaders are increasingly sidelined. Compensation for roles like VP of E-commerce has fallen sharply compared to five years ago, leading many experienced leaders into fractional or interim roles rather than full-time executive positions. This reflects a reduced willingness by companies to invest heavily in seasoned digital leadership.

Hollowing out of the middle and loss of institutional expertise

Organizations still maintain C-suite digital ownership (often under CMOs), but the layers beneath are increasingly filled by leaders new to e-commerce. Many veterans who helped build digital retail during its formative years are no longer embedded inside companies, creating a gap in applied experience, pattern recognition, and innovative mindset.

Innovation risk in the age of AI and agentic commerce

With AI, LLMs, and agentic systems posing existential strategic questions, the lack of empowered internal digital leaders is concerning. Consultants can advise, but they lack political capital and long-term accountability. True innovation requires internal leaders willing to take risk, own transformation, and push bold strategies—something currently missing in many organizations

Interim leadership has limits

While interim CMOs or fractional executives can help stabilize or transition organizations, this model can dilute innovation if overused. Transformation requires leaders with “skin in the game,” not rotating or part-time executives whose tenure and authority are inherently limited

Talent turnover and short executive tenures compound the issue

CMO turnover has long been high, but the combination of short tenures and interim leadership further weakens long-term brand and digital strategy. This environment makes sustained innovation especially difficult for legacy retailers trying to modernize, rather than for new digital-native entrants

#watsonweekend @leadership #ecommerceleadership

This week's Watson Weekend episode features hosts Rick Watson and Jessica Lesesky, who deliver a news analysis in an entertaining Headline Hangover, plus holiday advertising commentary you do not want to miss.

The show reflects on a turbulent retail year, previews a memorable holiday Jeopardy-style episode, and features an in-depth interview with James Lang, Head of Marketplace at Ulta Beauty.

Holiday Advertising Recap

Underwhelming holiday ads in 2025, with many brands recycling familiar creative.

Notable highlights:

The Farmer’s Dog: emotional, pet-focused storytelling that resonated strongly.

LEGO: creative anti-doomscrolling message that celebrates play and imagination.

Amazon: reused a proven holiday ad, reinforcing speed, convenience, and family moments rather than novelty.

Headline Hangover

Major retail headlines discussed:

Uber + Shopify: Partnership enabling one-hour delivery for millions of merchants, intensifying last-mile competition with Amazon.

Walmart: Expanded drone delivery pilots (Atlanta and other metros), following earlier success in Dallas–Fort Worth.

Saks Global: Deep financial distress highlighted by delayed vendor payments, revenue declines, EBITDA losses, and aggressive discounting—raising concerns about long-term viability.

Urban Outfitters: Adoption of an AI-powered supply chain compliance platform to manage regulatory complexity, traceability, and supplier data.

James Lang, Head of Marketplace, Ulta Beauty, joins the show to discuss Ulta Beauty’s marketplace, which launched in October 2025.

Ulta Marketplace Strategy

Positioned as the “second floor” of Ulta’s digital store, not a separate experience.

Fully integrated: one cart, one checkout, loyalty rewards, and easy returns.

Invite-only marketplace with curated, brand-direct sellers (no resellers, no buy box).

Core Principles

• Guest-first mindset: trust, consistency, and ease matter more than fulfillment mechanics.
• Brand protection: brands do not compete against themselves; authenticity is non-negotiable.
• Asset-light, margin-accretive model: reduces inventory risk while expanding assortment.

Internal Alignment

• Strong executive sponsorship and cross-functional buy-in.
• Marketplace seen as a strategic growth lever, not a side experiment.

The Watson Weekend is sponsored by Mirakl.

“In commerce, you don’t need another tool. You need a growth partner. The Mirakl platform is powering the next era of retail for the brands and retailers ready to move. Powered by AI and built for what’s next."

Chapters

Introduction - 0:00

Headline Hangover - 7:39

Introducing James Lang - 19:21

Show ends - 57:13

#watsonweekend #marketplace #retail #ultabeauty

Watson Weekend host Rick Watson is joined by Nick Kaplan for the week's retail and e-commerce news. The headline hangover contains results from Black Friday and Cyber Monday, and Amazon is testing 30-minute deliveries. The company's AI assistant Rufus continues to make headlines. There is also a discussion on the closing of Omnicom's IPG acquisition.

The week's special guest is Trevor Testwuide, CEO and Co-Founder of Measured, who talks about marketing measurement being broken, incrementality, and the problem with ROAS.

Holiday Recap: Black Friday & Cyber Monday

Black Friday delivered stronger-than-expected results; Cyber Monday was surprisingly muted with fewer real-time pundit updates than usual. Shopify’s admin and checkout systems experienced downtime during Black Friday, creating chaos for brands needing to adjust promotions or track performance.

Changing consumer behavior: Traditional Black Friday “doorbusters” and in-store frenzy continue to fade. Promotions now stretch well before and after the holiday.

Amazon Headlines

30-Minute Delivery

Amazon is piloting 30-minute delivery in select cities using micro-fulfillment centers, targeting high-frequency, convenience-driven categories (snacks, coffee, toilet paper, household essentials).

This pushes deeper into Instacart/DoorDash territory and raises expectations for ultra-fast delivery nationwide.

Rufus AI

Amazon’s shopping assistant continues expanding across the site. The hosts question whether Rufus drives incremental sales or merely accelerates discovery for customers who would have purchased anyway. Strong use case: summarizing product info, filtering five-star results, and translating reviews into clearer insights.

Agency Consolidation: Omnicom × IPG

The Omnicom–IPG deal closes, continuing the “big gets bigger” trend in advertising and media agencies. Thesis: scale enables more efficient data use and technology investment, but real-world synergies rarely reach the promised levels.

Rising AI adoption places mid-market agencies at risk, amplifying consolidation pressure.

The core of the episode is a deep discussion between Rick Watson and Trevor Testwuide on marketing measurement, attribution, and incrementality.

Why Marketing Measurement Is Broken

For years, the industry relied on Last-touch attribution, in which the channel closest to the sale gets 100% credit.

Multi-touch attribution (MTA) tries to map every impression and click across the buyer journey. MTA became unreliable after 2016 due to privacy walls and tracking limitations. Many brands still rely on outdated methods because they’re easy, familiar, and embedded in reporting workflows.

Incrementality: The Modern Standard

Incrementality answers the real question:

Did this ad actually cause additional sales, or would they have happened anyway? It isolates causal impact from correlated behavior—critical when high-intent shoppers convert regardless of ads.

Media Mix Modeling (MMM)

MMM provides long-term correlation analysis but not causality. Measured uses MMM combined with incrementality experiments to calibrate and improve accuracy.

Problem With ROAS

ROAS is simple but misleading—especially for bottom-funnel channels that “harvest” demand. Replacing ROAS with incremental ROAS or incremental contribution margin gives more truthful signal.

Why CFOs Love Incrementality

It speaks the language of finance: causal return, marginal contribution, efficiency. When incremental data confirms executives’ intuition about overspending in low-value channels, support for change accelerates.

The Watson Weekend is sponsored by Mirakl

“In commerce, you don’t need another tool. You need a growth partner. The Mirakl platform is powering the next era of retail for the brands and retailers ready to move. Powered by AI and built for what’s...

Rick Watson, Jessica Lesesky, and Nick Kaplan warm up the show with jokes about last week’s performance and introduce the episode’s segments. They highlight Jeoparty, Headline Hangover, and the week's special guest, Kelly Goetsch.

Headline Hangover: The team guesses blacked-out words from recent retail and e-commerce headlines.

* Levi’s chooses Microsoft to deploy AI- and agentic-commerce solutions internally to improve efficiency and collaboration.

* Lowe’s builds out its $8.8B wholesale business as DIY slows, reflecting macroeconomic pressures, rising material costs, and softening home-improvement demand.

* Whatnot looks like “all of commerce” — The livestream shopping platform is booming:

~$6B GMV, 140+ categories, 20M minutes of live content viewed last week, strong traction with younger audiences, and zero legacy tech debt → accelerated innovation with AI tools like Snap List.

Rick “wins” Headline Hangover—the group jokes that this is a rare event.

Kelly Goetsch from Pipe17 joins the show to discuss the launch of The Order Network Exchange (onX) and the Commerce Operations Foundation.

The industry lacks a standard for connecting selling channels to fulfillment systems. Every OMS, WMS, 3PL, and marketplace uses different formats, leading to slow integrations, high operational overhead, fragile point-to-point connections, and fragmented inventory visibility.

The Solution

onX Standard + MCP (Model Context Protocol)

Defines standard tools and resources for order, inventory, and fulfillment data.

Allows AI agents to consistently query backend systems.

Gives vendors interoperability without bespoke APIs.

Makes OMS and 3PL systems more “swappable

The Commerce Operations Foundation has 62+ members, including major OMS vendors like Manhattan, IBM Sterling, Kibo, Fluent, etc.

Goal: Full standard published by January 1, 2026, with implementations rolling out in Q1–Q2 2026.

MCP allows AI heads (GPT, Claude, etc.) to speak directly to order systems:

“How many orders today?”

“What’s the inventory of pink socks?”

Reduces dependence on hacky webhooks.

Jeoparty Part Deux:

A retail spin on Jeopardy with categories such as:

* Chapter Eleven (Nick Kaplan's love language)

* Did Tobi really say this?

* Sam Alt-Delete (AI & Sam Altman themed)

* M&A

* New kids on the block (e-commerce edition)

* Easy pictures

Memorable Answers

Joanne's bankruptcy

TikTok Shop / Shein confusion

Tariff schedules with a wreath

“Year of the Discount”

Walmart + Vizio acquisition

GEO → the new SEO

The Watson Weekend is sponsored by Rithum

In commerce, every second counts.

Rithum connects every channel with AI automation and insights,

helping brands grow profitably across marketplaces, dropship, and retail media.

Learn more at rithum.com

#watsonweekend #ai #jeoparty #onx

The Watson Weekend hosts, Rick Watson and Jessica Lasesky, and guest Nick Kaplan discuss retail and commerce trends for Q4 and 2025. This week’s headline hangover includes the resurgence of Toys R Us, Airbnb's pilot kitchen stocking service with Instacart, and the integration of AI to enhance efficiency rather than replace humans.

The Big 2025 “Jeoparty” Retro Game

Jeoparty host Jessica Lasesky uses the Watson Weekend version of the popular TV game show Jeopardy to try and confuse or showcase the brilliance of Rick Watson and Nick Kaplan. What did the previous Watson Weekend guests have to say about categories/topics such as Riddle Me RMN, Culture Club, AI Illuminati, Marketplace Mayhem, and Things Rick Said That Shouldn’t Be on Record?

AI & Tech Themes (AI Illuminati)

AI will not replace humans — it will reveal them

Beyond the Hype: The Future of Commerce, AI, and Human Creativity with Dilip Keshu

Shopify Summer ‘24 Edition is described as “AI for AI”

A running joke that it was peak AI hype, - Shopify Editions Recap Conversation With Shopify Agencies

Kristen Wiley: Half of AI tools were built to write… LinkedIn posts - Influencer Marketing Should Be A Car That Can Be Driven Anywhere with Kristen Wiley

What AI still cannot automate: “judgment” (or taste) - How a 115-Year-Old Company Uses A Framework That Contains Bridges, Boats, and Moats with David Katz and Beyond the Hype: The Future of Commerce, AI, and Human Creativity with Dilip Keshu

Culture & Leadership Themes (Culture Club)

“No courage in consensus.”

Jo Baker from https://www.youtube.com/watch?v=ym5QZpt3xzM

“Empathy doesn’t slow performance — it scales it.”

Donna Felix from https://www.youtube.com/watch?v=Lb1K--Ylvd8

The winning blend of traits: IQ + EQ + adaptability (AQ)

Donna Felix from https://www.youtube.com/watch?v=Lb1K--Ylvd8

Advertising and Retail Media Networks (Riddle Me RMN)

The word Kiri Masters swore she’d never say again in 2025 -Incrementality

From https://www.youtube.com/watch?v=pQv5rWAAfNs

Marketplace & Retail Themes (Marketplace Mayhem)

“Everyone’s a disruptor… until the invoice shows up.”

Jack Freeman from https://www.youtube.com/watch?v=vJTDWyWqXmI - VC perspective: marketplaces sound utopian until the economics hit.

Sellers say marketplaces “empower sellers”—but sellers call it:

“Commission with extra steps.

A discussion of:

- Ulta launching a marketplace and a future episode.

- Beauty brands rising through TikTok.

- The need to balance seller and buyer incentives.

Marketplace guests:

Michael McCluskey, from Lowe's - https://www.youtube.com/watch?v=8bMxX83kcPo

Logistics & Ops (Flexport Says What)

Delivery is the last touchpoint with the customer

John Shea from https://www.youtube.com/watch?v=ydQpB23iEf4

Golden rule: “Over-communicate and never miss a promise date.”

Nate Skiver...

The Watson Weekend hosts Rick Watson and Jessica Lesesky discuss the most important retail and e-commerce news from the past week. In the Headline Hangover, they discuss retail's Q4 challenges, AI's impact on brick-and-mortar stores, and retail media trends. They highlight Amazon CEO Andy Jassy's view that AI will accelerate the decline of physical retail, and discuss ThredUp's new peer-to-peer selling model. The hosts also address concerns about agentic commerce liability and Coca-Cola's use of generative AI in advertising.

The episode includes an interview with Liam Fuller, an 18-year-old entrepreneur from Ireland who founded three companies and now runs Source, an AI operations tool for retailers. Liam explains how Source integrates with legacy systems to help operations teams access data and perform tasks more efficiently.

He discusses the challenges of entering the US market, attracting engineering and sales talent, and balancing product development with business growth. Liam emphasizes the importance of product-market fit, cautious scaling, and targeting mid-market brands with complex back-office needs.

He notes the rapid advancement of AI models and the mixed reactions among retail executives, ranging from fear to enthusiasm.

The conversation concludes with advice for new founders and reflections on the evolving retail technology landscape, underscoring AI's transformative potential and the need for startups to innovate within traditional verticals.

The Watson Weekly is sponsored by Rithum

In commerce, every second counts.

Rithum connects every channel with AI automation and insights,

helping brands grow profitably across marketplaces, dropship, and retail media.

Learn more at rithum.com

Chapters

00:00 - Introduction

02:50 - Headline Hangover

15:17 - Introducing Liam Fuller

21:15 - How do you pitch brands?

24:42 - Hiring developers in France

26:11 - Evaluating sales talent

33:50 - Focus for the next 6 - 12 months

36:40 - Product market fit

41:50 - Go to market

44:49 - What does Source do?

51:26 - Too many AI startups?

54:27 - AI and retail trends

57:20 - End of show

#watsonweekend #ecommerce #ai #erp

The Watson Weekend Halloween Special hosts Rick Watson, Jessica Lesesky, and Nick Kaplan discuss 2025 retail and tech headlines with a Halloween twist. Think of it as the e-commerce and retail news version of Saturday Night Live, but it happened on a Friday.

The headline hangover features criticism of Pinterest's AI-powered personalization as a rebrand, analyzes Amazon's 14,000 job cuts as a culture and organizational issue rather than AI-driven, and discusses the growing role of AI agents in e-commerce,with retailers expected to adopt them. Target's holiday marketing includes bringing back Hot Santa. Comcast is innovating with programmatic ad buys that include linear TV, while WPP launches an AI platform aimed at SMBs to simplify marketing without agencies.

The hosts then play a game of retail trick-or-treat, which highlights ongoing retail struggles, including store closures, a resurgence of counterfeit goods, challenges with chatbot customer service, and aggressive price competition that threatens margins. They foresee a difficult holiday season with margin pressures and potential bankruptcies.

The Watson Weekend is sponsored by Mirakl. Growth isn't just about speed; it's about direction. Mirakl gives you the infrastructure to scale. smarter, not just faster, with marketplace, dropship, retail media, and a seller platform powered by AI and built for what's next.

00:00 - Introduction

04:37 - Headline hangover

26:06 - The scariest stories of 2025

30:12 - Who wins in Q4

33:42 - A Halloween dance

33:54 - Show ends

#watsonweekend #halloween #retailclosure #counterfeit #chatbot