The Great Ecom Debates of 2025: Truth, Trash Talk & a Little Tech Therapy
If you’ve ever been to an eCommerce event where “thought leaders” toss buzzwords like tinsel at a fourth-quarter holiday sale, you know the pain. Endless panels. No hot takes. Everyone nodding in violent agreement while quietly plotting their next LinkedIn post.
Well, Shoptalk 2025 wasn’t that.
In fact, we decided to flip the format entirely on its head—like a first-time DTC founder trying to configure Shopify scripts. Instead of your standard sit-around-and-smile fireside chats, we hosted debates. Real ones. With sides. With voting. With blood on the digital floor (figuratively, but maybe also literally if you count some of the headless vs. monolith shade).
Let’s break it down.
Replatforming: Strategic Leap or Fyre Festival?
Our first throwdown? The business case for Replatforming. Sounds straightforward until you realize most business cases for replatforming are held together with rainbows, unicorn tears, and a strong whiff of optimism.
Vince Santo brought the pragmatic hammer: know your costs, know your platform’s limits, and for the love of your CFO’s sanity—don’t build a case based on dreams. Chris Silver, never one to play it safe, clapped back with Fyre Festival references and a hard truth: your tech stack won’t save you if your org’s a mess. Replatforming can be necessary, but it’s not a miracle cure for a broken team or misaligned ops.
Winner: Vince by a hair. CFOs everywhere breathed a sigh of relief that replatform business cases can actually be made to work.
Headless vs. Contained: IQ vs. AQ
Next up: the heavyweight battle of architecture philosophies.
Victor Castro sang the gospel of headless like it was handed down from the Gods of Headless. Custom CX, lower dev costs (debatable), front-end freedom, and API glory.
Nick Kaplan, however, didn’t come to play. His argument? Headless is the IQ play, but adaptability (AQ) wins commerce. You want optionality? Cool. But try shipping fast and fixing bugs with a dev team spread across six time zones. Simplicity scales, and if you're Fashion Nova or Skims, monoliths aren’t slowing you down.
Best line of the night? “You don’t need to be close to your codebase—you need to be close to your customer.”
Winner: Kaplan, with a mic drop. I’m not kidding, Nick literally broke the microphone!
Can Replatforming Be... Enjoyable?
“Enjoyable” and “replatform” in the same sentence? That’s like saying “relaxing” and “Q4 planning.” But Mark Rubin gave it a go—positioning expert system integrators (SIs) as your kitchen-reno pros. You could DIY your platform migration, but don’t complain when you’re washing dishes in your bathtub.
Tarek Müller, co-founder of Scayle, came in with a more skeptical (and brutally honest) angle: many SIs say they’re experts, then recommend legacy tech that maximizes their hours and your pain. You want a better experience? Vet your SI like you’re picking a tattoo artist. And keep some control in-house. Ownership > Outsourcing.
Outcome: A dead heat. Mark made the case. Tarek dropped the reality check and squeaked out as the winner of this debate.
AI & the Future Org: Lights Out or Light On?
Last but not least—AI and the death (or evolution) of the eCom org chart.
Rob Garf made the case that we’re not killing jobs—we’re reshaping them. AI doesn’t mean 75% layoffs, it means new skills, new roles, and better leverage of startup-level speed without enterprise-level bloat.
Rama Aluri brought nuance: yes, AI will transform roles, especially in ops, but context matters. Mid-sized retailers won’t invest like AWS, and high-touch categories will still need human judgment. AI is a change, not a replacement.
Verdict: Rob edged it out. Not because AI is a silver bullet, but because he made you believe it could be—if you’re smart about it.
Final Thoughts: Less Fluff, More Fire
Shoptalk 2025 proved one thing—eCommerce isn’t short on opinions. But what we lack is venues for actual debate. Not panels. Not LinkedIn humblebrags. But space where people can push each other to say what they really think—without hiding behind the PR version.
That’s what these debates were about. And judging by the crowd, the votes, and the whispers after every mic drop, the industry is ready for more.
So here’s my promise: this wasn’t a one-off. The Great eCommerce Debates will return—with sharper topics, hotter takes, and hopefully a few more red cards flying across the room.
Because progress doesn’t happen in echo chambers. It happens in the ring.
Expert Consulting: How Will You Grow Your eCommerce Company?
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Mistakes are expensive. They cost money, of course. What’s worse is the opportunity cost. I work with investors and management teams worldwide to help them get a handle on their digital business plans to execute a clear path forward.
For more Shoptalk Content, check out our Youtube playlist dedicated to events just like it:
