Entrepreneurs on Fire Shopify's Winter '26 Edition: Point of Sale Upgrades with Ray Reddy
Jan 28, 2026
Ray Reddy, VP of Retail at Shopify and former co-founder of Ritual, talks about Shopify's POS 10 and modern retail solutions. He covers simplifying staff workflows, solving mixed-order checkout, and improving search and navigation. He also discusses unifying online and in-store systems, expanding delivery and payment options, and how AI will make customization easier.
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Continuous Improvement Focus
- Shopify continuously iterates products based on customer feedback to simplify complex workflows.
- Ray Reddy frames improvement as making staff and stores more successful by reducing friction.
Enable Mixed Fulfillment In One Cart
- Allow mixed fulfillment methods in a single transaction to avoid awkward workarounds.
- Split fulfillment line-by-line so staff can ship bulky items and carry out small items in one order.
Branding Improves In-Store Trust
- Merchants saw better in-store trust when checkout matched online branding with colors and logos.
- Ray notes that visual trust helps upsells because the UI feels native to customers.
