Ep 174: Shopify Winter Editions 2026, with Ben Homer Senior Solutions Engineer at Shopify

In this episode, I sit down with Ben to talk through Shopify's Winter Editions 2025, now that the dust has settled from the initial announcements.

Ben walks me through how Shopify approaches AI, both internally and for merchants. Inside the company, everyone has access to an internal LLM proxy and cutting-edge tooling. That same thinking flows out to the platform: help brands show up where customers are, which now includes AI chat interfaces, and make operations faster through better tooling.

We spend time on agentic commerce, what it means beyond the buzzword, and why it matters for how people will shop. Ben explains the ideas behind Sidekick's evolution and SimGym, which lets any brand test site changes against Shopify's anonymised consumer dataset before going live.

The standout for me is how these features connect. SimGym paired with the new Rollouts feature, which handles scheduling and traffic management, creates something that previously required multiple third-party tools. Ben also flags the POS Hub, Shopify's hardware connectivity layer, as worth watching for anyone thinking about retail.

Practical, detailed, and useful if you're building on Shopify or just trying to work out what's worth paying attention to in this release.

Checkout Factory here.

Sign up to our newsletter here.