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.
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Guest Resources
Shopify Winter ’26 Edition – Learn more about Shopify’s retail solutions and the Winter ’26 Edition.
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.
Sponsors
HighLevel: The ultimate all-in-one platform for entrepreneurs, marketers, coaches, and agencies! Learn more at HighLevelFire.com!
Intuit QuickBooks: Transform your cash flow and your business this year! Check out QuickBooks money tools today! Learn more at QuickBooks.com/money! Terms apply. Money movement services are provided by Intuit Payments Inc., licensed as a Money Transmitter by the New York State Department of Financial Services.
Show Notes
**Click the time stamp to jump directly to that point in the episode.
Today’s Audio MASTERCLASS: Shopify’s Winter ‘26 Edition: Point of Sale Upgrades
[1:12] — Ray shares something that he believes about becoming successful that most people disagree with.
- Be willing to put in the reps and put in the work.
[2:12] – Ray talks about what Shopify Edition is and why does it matter for retailers.
- AI is driving a modern renaissance in entrepreneurship.
- Shopify aims to simplify complexity so retailers can focus on results.
- More people are starting retail businesses than ever before.
- Creativity, building, and scaling with technology have never been more accessible.
[3:46] — Ray talks about what are the retail updates that are included in the Winter ’26 Edition.
- Expanding retail payments to Luxembourg, Switzerland, and the Czech Republic.
- Tap to Pay on iPhone now available in Germany, Ireland, New Zealand, and Spain.
- Support for local payment methods such as Cart and Care.
- Retail Markets now works with catalogs for easier multi-region management.
- New inventory upgrades, including in-store stock counts directly from POS with extensions.
- Subscriptions can now be sold directly in-store at POS including discounts for subscribing customers.
- Retailers can mix and match “Lego block” features to create custom solutions.
[6:49] — Ray shares a real-world example of Shopify’s retail evolution.
- David’s Bridal: a 75-year-old brand reinventing itself on Shopify.
- Leveraging Shopify to build an “endless aisle” marketplace for all wedding-related services.
- Proof that established retailers can transform through technology.
[8:44] – A timeout to thank our sponsors.
- Intuit QuickBooks: Transform your cash flow and your business this year! Check out QuickBooks money tools today! Learn more at QuickBooks.com/money! Terms apply. Money movement services are provided by Intuit Payments Inc., licensed as a Money Transmitter by the New York State Department of Financial Services.
- HighLevel: The ultimate all-in-one platform for entrepreneurs, marketers, coaches, and agencies! Learn more at HighLevelFire.com!
[12:38] — Ray talks about what Shopify POS Hub is and why is it such a big deal.
- Retailers often experience device failures when iPads can’t connect to scanners, printers, and terminals.
- Bluetooth peripherals disconnect when tablets sleep causing the #1 retail pain point.
- Apple’s iOS limitations restrict driver-level integrations, leaving retailers stuck.
- Shopify POS Hub is a mini-computer that acts as a universal translator between iPads and all professional-grade peripherals.
- Plug in any USB printer, scanner, cash drawer, or scale and it just works.
- Retailers get a beautiful tablet POS and enterprise-grade hardware reliability.
[18:40] — Ray tells how different POS hub is from anything else on the market.
- It makes iPads compatible with almost any USB retail peripheral.
- Hub is an Apple-certified MFi device, ensuring stable, secure connections.
- This solves the historic incompatibility gap that kept large retailers tied to Windows-based terminals.
[19:36] — Ray explains the Shopify and Uber Direct partnership.
- Merchants can offer one-hour, same-day, or scheduled delivery right at checkout.
- Online store and POS integrate seamlessly with Uber’s entire delivery network.
- Expands customer convenience and merchant reach instantly.
[20:44] — Ray talks about one powerful move retailers should make right now.
- Adopt Shopify POS Hub to achieve 99.99% peripheral reliability.
- Eliminates downtime and boosts checkout speed and customer experience.
- Available for purchase at Editions with full hardware bundles.
[22:20] — Call to action
- Shopify Winter ’26 Edition – Learn more about Shopify’s retail solutions and the Winter ’26 Edition.
[25:00] – Thank you to our Sponsor!
- HighLevel: The ultimate all-in-one platform for entrepreneurs, marketers, coaches, and agencies! Learn more at HighLevelFire.com!
Killer Resources!
1) The Common Path to Uncommon Success: JLD’s 1st traditionally published book! Over 3000 interviews with the world’s most successful Entrepreneurs compiled into a 17-step roadmap to financial freedom and fulfillment!
2) Free Podcast Course: Learn from JLD how to create and launch your podcast!
3) Podcasters’ Paradise: The #1 podcasting community in the world!
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