Shopify's Winter '26 Edition: Point of Sale Upgrades with Ray Reddy
Entrepreneurs on Fire
John Lee Dumas
4.8 • 4.1K Ratings
🗓️ 28 January 2026
⏱️ 22 minutes
🧾️ Download transcript
Summary
Ray Reddy is VP of Retail at Shopify, leading the company's retail business and championing local entrepreneurs. With a career focused on leveraging technology for commerce, he previously co-founded Ritual, a mobile commerce platform supporting local restaurants, and PushLife (acquired by Google), where he later led mobile product management for shopping and commerce. Ray is passionate about building products that simplify complexity and create new opportunities to help local entrepreneurs win.
Top 3 Value Bombs
1. Retailers are entering a modern renaissance where AI and rapid innovation make entrepreneurship easier than ever.
2. Shopify POS Hub delivers near-perfect reliability by solving the long-standing pain of iPad-peripheral incompatibility.
3. Expanding delivery and payment capabilities, like Uber Direct and global Tap to Pay, helps merchants offer world-class customer experiences.
Learn more about Shopify's retail solutions and the Winter '26 Edition - Shopify Winter '26 Edition
Sponsors
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Transcript
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| 0:00.0 | Boom. Shake the room. Fire Nation. JLD here. And welcome to Entrepreneurs on Fire, brought to you by |
| 0:08.5 | High Level, the all-on-one sales and marketing platform. Today we'll be breaking down Shopify's |
| 0:13.0 | winter of 2026 edition point of sale upgrades. To drop these vibe bombs I brought to Ray Ready |
| 0:18.1 | and the EO Fire Studios, Ray is VP of retail at Shopify, leading the company's retail business and championing local |
| 0:24.1 | entrepreneurs with a career focused on leveraging technology for commerce. |
| 0:27.4 | He previously co-founded Ritual, a mobile commerce platform supporting local restaurants |
| 0:31.8 | and push life, which was acquired by Google, where he later led mobile product management |
| 0:35.8 | for shopping and commerce. |
| 0:37.2 | Ray is passionate |
| 0:37.8 | about building products that simplify complexity and create new opportunities to help local |
| 0:41.9 | entrepreneurs win. And today we talk about retail updates breakdown, Shopify POS Hub, |
| 0:47.5 | solving pain points, and oh, so much more. And a big thing of us marching today's episode |
| 0:51.8 | goes to Ray and our sponsors. Are you ready for the ultimate all in one platform for entrepreneurs, marketers, |
| 0:59.2 | coaches, and agencies, build funnels, automate follow-ups, manage clients, and even |
| 1:04.4 | white label your own software. |
| 1:06.6 | Say hello to our featured partner high level and visit high level.com to start your free trial |
| 1:15.3 | today. |
| 1:17.7 | Ray, say what's up to Fire Nation and share something that you believe about becoming successful |
| 1:23.7 | that most people disagree with. |
| 1:27.0 | Hey, John, I'm going to say something real boring. |
| 1:29.8 | I think one of the most underrated things is just good old-fashioned hard work. |
| 1:34.3 | You hear about all of the hacks to become successful. |
... |
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