Jam Sesh Recap: Curiosity at Work
There are plenty of conferences where you sit through glossy slides, polite Q&A, and a few vendor pitches. Jam Sesh wasn’t that.
On September 17th, we gathered 50+ retail leaders in one room and basically said: let’s drop the polish. Instead of predicting some AI future 10 years out, we focused on the messy middle: what leaders are actually trying, what no one has figured out yet, and where it might make sense to start placing bets.
One attendee nailed it: “The intimacy of the format created space for real dialogue, thoughtful brainstorming, and actual connection.”And out of that space, one theme kept showing up: the best thing we can do right now is stay curious.
The Big Problem with AI
Most AI talks start with promises of transformation. Fayez Mohamood, CEO and Co-Founder of Bluecore and alby, started with the problems instead.
AI, he said, is still too abstract for most organizations. That makes it easy for big ideas to get shot down before they even start. Sound familiar? Back in 2000, headlines dismissed ecommerce as a fad. Meanwhile, Ralph Lauren was betting $200M on digital. History’s reminder: the biggest shifts rarely look obvious at the time.
Today, AI is at the same crossroads. Some say the website is obsolete, others say it’s never going away. Email is dead. Agents will revive it. Everyone’s got a take. But there’s no roadmap and no true experts — only the builders who are actually in the tools, testing, experimenting, and sharing what they find.
Fayez left us with four principles:
- Listen to the builders, not the pundits
- Think in outcomes, not inputs
- Free your data from SaaS jail
- And above all, keep an open mind — “yes, and” beats “no, but” every time
His parting note? It’s still early. Which is exactly why curiosity matters most.
Big Conversations
We kept the honesty rolling.
Ajit Sivadasan, President of Global eCommerce at Lenovo, joined Fayez for a fireside chat and reminded everyone to keep testing. Scale what works, cut what doesn’t, and expect to be wrong sometimes.
Then came the panel with DXL, Carhartt, Michael Kors, Tourneau | Bucherer, and Bluecore. Their verdict: AI doesn’t have a tech problem, it has a people problem. It’s a tool, not a magic bullet. The wins come when you shrink “days of work” into “hours,” but only if you have the right foundations in place. Education and data came up again and again — like one brand, who centralized 17 different data sources before layering AI on top.
Bottom line: every brand is experimenting. No one is “done.”
The Debate: Will the Website Go Away?
(Probably not, but it won’t stay the same either)
Then we had some fun. Frank Martinez (Shimano) and Nathan Decker (Evo) faced off on the question: Will AI agents replace the ecommerce website?
Frank said no: websites are the anchor of trust, discovery, and inspiration. Nathan argued yes: agents will do the heavy lifting, making the traditional site less important.
The crowd leaned hard toward Frank at first — 82% said websites aren’t going anywhere. But after the debate? Numbers shifted. A few fewer votes came in, Frank lost two, Nathan lost one. By technicality, Nathan took the win.
Not a knockout, but enough to show the tension. The takeaway wasn’t that websites disappear tomorrow. It’s that the way we use them — and the way customers expect to interact with them — will change dramatically.
Rolling Up Our Sleeves
After all that talk, it was time to build.
Bora Celik, founder of a/gentic led a workshop where teams designed agents that could truly change their businesses. Bora even showed how to build one live.
That struck a chord. Leaders often move away from hands-on learning as their careers advance. But agents bring it back. Or as Bora said: “I’ve learned more in the last year than in the previous ten.”
After that, we split into teams to design our own agents. The focus? What can we automate that could double our revenue or 10x efficiency?
Want to learn more about the agents we covered? Check them out here.
Key Takeaway: Get Curious
Jam Sesh wasn’t about answers. It was about questions.
One theme was constant: stop waiting for the perfect playbook. Stay open. Keep experimenting.
It’s still early, which is the best gift of all. The leaders who lean into the unknown with curiosity will be the ones who shape what comes next.
What’s Next
Attendees asked for more opportunities to connect in small, purposeful forums. We’re on it. Stay tuned for the next Jam Sesh near you.
And because every question asked went toward a good cause, we also raised $2,000 for the Harmony Program, supporting music education in underserved NYC communities.
One attendee put it best: “It was a truly unique and valuable experience, and I left feeling both energized and inspired.”
Same here. We can’t wait to jam again.
