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