The first Watson Weekend show of 2026 serves as a post-mortem for the NRF conference, where Rick Watson and Jessica Lesesky recap the live event held at the Asylum in New York City and share "Nostradamus-style" predictions for 2026.

The overarching theme for the coming year is "be bold," urging businesses to move past the economic hesitations of 2025.

The show highlights three major industry shifts:

The AI Wars: The hosts predict that Google’s Gemini will maintain its adoption momentum over OpenAI due to Google's vast data ecosystem, its integration into Android and Samsung devices, and its move to become the "default layer of intelligence" for the internet via the UCP protocol.

Nike’s Innovation Deficit: Despite a leadership change, Nike is criticized for losing its "cool" and "shelf dominance" by over-prioritizing Direct-to-Consumer (DTC) strategies at the expense of wholesale and its core running category. The hosts note that Nike’s margins are significantly lagging those of competitors like On.

Shopify’s Evolution: Shopify is seen as transitioning from a "storefront company" to an AI and payments powerhouse. With heavy investments in "agentic commerce," 2026 is expected to be the year these AI announcements deliver tangible results.

The episode concludes with a critique of the NRF conference itself, noting that while the industry is hopeful, many vendors are still failing to articulate the actual impact and data behind their AI products.

Housekeeping: Rick Watson is reorganizing the content for Watson Weekly and Watson Weekend, with an increased focus on the newsletter. There will be weekly interviews on Wednesdays, and the Watson Weekly remaining on Mondays. The Watson Weekend will move under the Watson Weekly banner as the weekend edition.

#watsonweekly #shopify #nike #shopify

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