Jam Sesh Recap: Meet Uncertainty with Curiosity
On September 17th, we brought together 50+ retail leaders for a giant Jam Sesh. Our intent was to break the mold of the traditional conference. Instead of pontificating on a future that’s impossible to predict, we opened the floor for conversations about what leaders are actually trying, what’s still unknown, and where we might start placing bets amidst the uncertainty.
By creating a space where it was ok to not have it all figured out, we made way for unencumbered collaboration. One attendee summed it up perfectly: “The intimacy of the format created space for real dialogue, thoughtful brainstorming, and actual connection.”
What emerged was clear: it’s still early. The best thing we can do is meet the uncertainty with curiosity. Don’t reject new ideas before they have the chance to take shape, and remember that the bets with the biggest potential rarely look obvious in the moment.
Opening Keynote: The Big Problem with AI
Most AI talks are about the promise. Fayez Mohamood, CEO and Co-Founder of Bluecore and alby, started with the problems instead.
AI is still too abstract for most organizations, which makes it easy to shut down promising initiatives before they start. Fayez reminded us this is nothing new. Back in 2000, headlines dismissed ecommerce as a fad, even as Ralph Lauren bet $200M on digital. The lesson: transformations never look obvious in the moment.
He pointed out that we’re in a similar place with AI today. The industry is polarized: some argue the website is obsolete, others insist it will never go away; some say email is dead, others believe agents will revive it. The reality? There is no roadmap and there are no experts. The only people worth listening to are the builders actually tinkering with the tools, testing them on day one, and sharing what works.
Fayez outlined four shifts retailers must embrace:
- Listen to the builders rather than the pundits.
- Think in outcomes, not inputs. Agents aren’t about APIs or processes, they’re about business results.
- Free your data from SaaS jail so agents can act on it.
- Change the culture by replacing binary thinking with “yes, and.”
And his closing reminder: it’s still early. No brand has it figured out. Which means the opportunity belongs to those who are willing to get curious and start experimenting.
Big Conversations
From there, we turned the mic to retail leaders who are actively navigating these shifts.
Fireside Chat with Ajit Sivadasan, President of Global eCommerce at Lenovo
Ajit Sivadasan shared a grounded but forward-looking perspective in his fireside chat with Fayez. His message was clear: the only way to move confidently in this environment is to test consistently. Scale what works, cut what doesn’t, and stay open to being wrong about your own biases. He reminded us that with AI there will always be a role for domain experts, which means leaders need to stay in constant learning mode and continue educating themselves as the landscape evolves.
Ajit also pushed the group to think specifically about content. He pointed to early research suggesting consumers dislike AI-generated content today but argued that may change as the technology matures. Translations, he suggested, are a smart place to start: a practical way to accelerate how quickly content can go live across markets without sacrificing quality.
Brand Panel with DXL, Carhartt, Michael Kors and Tourneau | Bucherer, moderated by Bluecore
The panel that followed brought the conversation down to the organizational level. The biggest theme: AI doesn’t have a tech problem, it has a people problem. Success depends less on the capabilities themselves and more on how teams adopt and apply them.
Panelists agreed that AI should be treated like a tool, not a magic bullet. Its power lies in taking processes that once took days and compressing them into hours, but it still requires strategy, oversight, and integration into real workflows. Education came up again and again as the unlock: one brand described tagging traffic to understand how much was AI-driven during the holiday season, giving them the clarity to make smarter investment decisions.
Another key point: data is the real building block. Without the right foundation, AI can’t deliver. One brand shared that they centralized 17 different sources of data into one system to make AI applications possible—an effort that underscored just how much organizational alignment is needed to unlock value.
The common thread across both sessions? Every brand is experimenting. No one is “done.”
The Debate: Will the Website Go Away? (Probably Not, But It Will Look Different)
The most spirited session of the day was a live debate between Frank Martinez, Head of DTC at Shimano, and Nathan Decker, Director of Ecommerce at Evo.
The question: will AI agents replace the ecommerce website within 10 years?
- Frank’s stance: The website isn’t going anywhere. It’s still the anchor for brand trust, discovery, and inspiration.
- Nathan’s stance: Agents will fundamentally reshape shopping, doing the heavy lifting so websites as we know them will become less relevant.
Before the debate, the audience voted overwhelmingly on Frank’s side, with 82% believing the website would not go away. But after hearing the debate, the numbers shifted. Three fewer people voted in the second round. Frank lost two votes, Nathan only lost one. By technicality, Nathan took the win.
Not a landslide, but that slim edge captured the real uncertainty in the room—and the reason debates like this matter. The bigger takeaway? The purpose of the website, and the way consumers engage with it, will change drastically.
Rolling Up Our Sleeves
The afternoon was all about building. Bora Celik, founder of a/gentic, led a workshop where teams designed agents that could truly transform their businesses. Bora also showed how to actually build an agent, live.
That hands-on approach hit a nerve. As leaders, we often lose the learning that comes from experimenting directly. But agents offer a chance to get hands-on again. As Bora put it, “I’ve learned more in the last year than in the previous ten.”
Want to learn more about the agents we covered? Check them out here.
Key Takeaway: Get Curious
If Jam Sesh proved anything, it’s that curiosity is the currency of progress.
From Fayez’s call to experiment, to Bora’s live building, to the spirited debate on the future of the website, the message was the same: stop waiting for the playbook and start trying.
Everyone left with the same encouragement: it’s still early. And that’s a gift. The winners will be the ones who lean into the unknown, keep asking the next question, and get hands-on with what’s possible.
Thank You
To every speaker, panelist, and participant—thank you for showing up with honesty and curiosity. To our facilitators and behind-the-scenes crew, you set the bar high.
Together, we also raised $2,000 for the Harmony Program, turning every audience question into support for music education in underserved communities in NYC.
What’s Next
Attendees asked for more opportunities to connect with peers in small, purposeful forums, and we intend to deliver. Stay tuned for the next Jam Sesh near you.
One attendee captured it perfectly: “It was a truly unique and valuable experience, and I left feeling both energized and inspired.” We couldn’t agree more.
This is just the beginning. We can’t wait to jam again.
