Shopify's Winter '26 Edition: Point of Sale Upgrades with Ray Reddy

0:01Boom! Shake the room, Fire Nation. JLD here and welcome to Entrepreneurs on Fire. brought to you by High Level, the all-in-one sales and marketing platform. Today, we'll be breaking down Shopify's winter of 2026 edition point-of-sale upgrades. To drop these value bombs, I brought to Ray Reddy and the EO Fire Studios. Ray 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 Push Life, which was acquired by Google, where he later led mobile product management for shopping and commerce.

0:37Ray's passionate about building products that simplify complexity and create new opportunities to help local entrepreneurs win. And today we talk about retail updates, breakdown, Shopify POS hub, solving pain points, and oh, so much more. And a big thank you for sponsoring today's episode goes to Ray and our sponsors. Are you ready for the ultimate all-in-one platform for entrepreneurs, marketers, coaches, and agencies, build funnels, automate follow-ups, manage clients, and even white label your own software, say hello to our featured partner, High Level, and visit highlevelfire.com to start your free trial today.

1:17Ray, say what's up to Fire Nation and share something that you believe about becoming successful that most people disagree with. Hey, John, I'm going to say something real boring. I think one of the most underrated things is just good old fashioned hard work. You hear about, you hear about all of the, I don't know, hacks to, to become successful. And I've just found that for the most part, just being, being willing to put in the reps and put in the work, uh, that, that, that's always been my strategy. We actually just said my favorite phrase. Cause people come to me all the time. They're like, John, how do we get good at podcasting or video or fill in the blank.

1:55And I always just say one thing, put in the reps. Nobody was good at anything until they got up every day for a significant amount of days in a row and put in the reps. So I love that start in Fire Nation. We're talking about Shopify's winter of 2026 edition, the point of sale upgrades. And I want to start by talking about Shopify edition, Ray. So tell us all about this. What is it? Why is this launch significant for retailers and business owners, which of course make up our audience, Fire Nation. This winter edition, I think is a, it's a special one. I think we really feel like we're, we're amidst a modern day Renaissance with AI really at the center.

2:37You know, it's like this transformative, this transformative moment where we can really help businesses find their place in this, in this new landscape. You know, the world is changing faster than ever. and really feel like we have a role to play here to connect all the powerful technology, all of the changes in the world and just help our merchants make sense of it and more importantly, use it in a way that actually delivers results for their business. So I think we're seeing more retailers, more merchants get a start than ever before. entrepreneurship has become, you could say, easier than it's ever been to get started.

3:21So it's, you know, lots of new possibilities, new beginnings, you know, creativity is getting easier. It's getting easier to build, build software, build extensions. So yeah, we think this is like a really special moment in time. I mean, Fire Nation, at the end of the day, results. Results are what matters. And this is why I love Shopify, because they always focus on getting you the results. So I want to talk about the retail updates and really kind of have a breakdown about that, Ray. What are these retail updates that are included in this edition? I mean, walk us through the new features and what they aim to solve for merchants specifically.

4:00We talked about putting in the reps. Like this was, you know, I feel like in the last six months, the retail team has just, has been really putting in the reps. So we have a, we have a slew of launches, I'll talk about eight to ten of them, but there's one in particular that I think we want to really focus on that I think is a really, really big deal. It's been one of the biggest pain points our retailers have had over the years. So I'll save that for the end, but I'll just quickly talk through a number of things that I think are worth highlighting. So one is a lot of our brands are international.

4:37They work across many countries. And so one important thing is just expanding our footprint. So online Shopify is in 175 countries. Retail isn't in that many countries. So this has been another big focus for us to expand that. So we now have retail payments in Luxembourg, Switzerland, the Czech Republic. We've expanded tap to pay on iPhone and we've added Germany, Ireland, New Zealand, Spain. We have a cool Uber direct partnership that we'll talk about later as well. You know, another thing as you go into a lot of these international countries, like accepting local payment methods is really important in some of these places.

5:18So we now have a cart plan care support. And then going more into like some of the back office stuff, retail markets now works with catalog so just making it easier to manage your presence across various geographies we just continue to upgrade everything we're doing with inventory and making that easier so we now launched a new ability to do stock counts in store right off the POS with an extension another thing that's been long asked about is subscriptions so excited to say that you can now actually sell subscriptions directly on Shopify POS so what that means is if someone comes in and you want to sell a monthly subscription you can actually just do that right as they're paying it can enroll them into an ongoing subscription you could always do this online but this was one of the gaps in the store And are they also able to like offer a discount if they choose subscription at that point at the checkout?

6:26Totally. Oh my God. That's genius. You can, this is, you know, this is the Lego blocks that you get with Shopify that you can just mix and match. I love it. Now, can you think of an example of a company that's doing this great right now? Maybe take a moment, think about a company that's using Shopify and using some of these retail updates or Shopify edition in a way that you think is really cool. Maybe we can give them a little spotlight, a little shout out right here. What are they doing well within this that you're like, okay, this is what this was meant for. This is why we built these features.

7:03I think one of the most inspiring stories I've heard of in 2025 was David's Bridal that recently came on Shopify. They're a 75-year-old company founded in 1950 that is reinventing themselves. And I think it's an inspiring story of just how a retailer with such deep roots has such a vision of growth for the future with a technology platform like Shopify. I think that they're really transforming. We've heard of a lot of retailers that have added marketplaces online. That's been a trend that we've seen. And one of the things that David's Bridal realized is that they touch something like 80 % of all brides.

7:56It's some absurdly high number that kind of rotate through their stores or their website. And one of the things they realized is that they can offer this like an endless aisle and start to expand even beyond just selling just the apparel and dresses to all of the experiences and services that brides may need for their weddings. And I just think that, you know, they're early in the journey of doing that. But I just think that that's like such an inspiring story of transformation, of going from, you know, just being a retailer to like solving a really painful problem of matchmaking across so many different, you know, service providers.

8:50So I thought that was really, really cool. Yeah. And I love that example because examples like that, they just really bring to life exactly what Shopify is doing and just how much you're helping, you know, your users and your customers and your clients, because now we can see that in action. And we have so much more to talk about around this fire nation when we get back from thanking our sponsors. It's January. And that means new goals for your business. And because I know you actually want to hit those goals, it's time to stop messing around and start knowing exactly what's happening with your money.

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11:05On top of it all, their support team is second to none and has your back every step of the way. Seriously, every question that pops up, they will have your answer waiting. And if you visit my special partnership link, you'll get a free trial. So visit highlevelfire.com to start your free trial and see why thousands of businesses are switching. That's highlevelfire.com, where marketing, sales, and automation finally come together. High level, join the revolution. Ray, we're back, and I want to talk about Shopify POS Hub. How does the POS Hub fit into Shopify Edition? And specifically, what role is it meant to play for retail operations?

11:46I'll just go back to this moment when you're setting up a retail store, you've got your iPad ready to go, and you plug in your barcode scanner, and nothing happens. And it's just that sinking feeling when you realize that this$300 receipt printer you bought just doesn't work with your sleek new POS setup. I think this is the problem that we're here to talk about because Shopify is about to change the game on this entirely. The problem, why this happens is many retailers today want a beautiful POS with a sleek tablet. For Shopify, the vast majority of our retailers choose iPads. the challenge is that on a Windows PC, a manufacturer can write what's called a driver that basically allows software on a computer to talk to these various devices.

12:52The problem was it's a bit of the Wild West. Anyone can do anything. And so when Apple was building iOS, they looked at all that chaos and decided they weren't going to go in that direction. for many legitimate reasons. One was security. They didn't want random companies to be able to inject code into their system. There was stability. Windows is notorious for crashing because of bad peripheral drivers, and Apple has been able to eliminate this entirely. That is like battery life. Apple wants very optimized power usage on portable devices. So that's all great, except the frustration that that has caused, especially in the POS world, is that your multi-thousand dollar iPad Pro often can't talk to a basic USB printer.

13:45And if you want that professional barcode scanner with advanced features, it just won't work with an iPad. Bluetooth has been an option. So this is why most POS systems have gone to Bluetooth route, connecting with Bluetooth peripherals. But even there, there's a ton of problems. In fact, this is the path that Shopify has gone down historically as well. The challenge is that tablets go to sleep. When they go to sleep, the Bluetooth connections tend to disconnect in the background. And so unfortunately, what happens is right when you want to go make that sale, you might find that your barcode scanner isn't connected and you have to go reconnect it via Bluetooth.

14:32Even worse, your payment terminal may not have been connected or that receipt printer that you were trying to finally print that receipt out lost its connection. And so this has been one of the... It's represented, I think, close to 40 % of all of our support tickets over the last many years. It's been the biggest pain point for our retail merchants by a long mile. And there isn't really an easy solution to this problem. One of the things that, the way that Apple solves this is they have a program called MFI, it stands for made for iPhone. But the challenge with that is it's expensive. So many peripheral makers skip that.

15:22Most professional grade retail peripherals were sort of built for Windows PCs. And many of them have not gone and recertified their peripherals for the Apple ecosystem. There's wonky workarounds that people use. And in some cases, this is actually why large enterprise brands and larger retailers haven't moved to modern tablet-based systems. This is actually a really big reason. They have to stay on Windows terminals if they want the professional-grade peripherals that they're used to. And that's until today. And this is where, you know, enter Shopify Hub. And the genius of it is, instead of fighting sort of the challenges in the ecosystem, we really embraced it.

16:15Hub is really a mini computer running inside of a small device that looks like a USB hub. And it's basically a universal translator between your iPad and everything else. So you plug your receipt printer into the hub, you plug your barcode scanner and you plug your cash drawing just like you would into a PC. And even the weird scale you might need for your deli counter, it just all works. And where it gets really interesting is that it's really rethinking what a tablet-based point of sale can be. you can now kind of have your cake and eat it too. You can have a modern, beautiful PLS and all of the professional enterprise-grade peripherals that maybe you've already purchased, maybe you need it going forward, but it just bridges kind of like the old ecosystem with the new ecosystem.

17:14It's super powerful and we're really excited about it. Well, you really did do a deep dive right there on the pain points that it solves. I mean, it addresses pain points for retailers, you know, and obviously you talked about, you know, where traditional point of sale tools fall short in comparison to what this is going to be. You also made a couple of points about, you know, what sets it apart, but let's kind of maybe dive just a little bit deeper in that point, because, you know, let's be honest, it's a crowded retail tech space. So what specifically makes Shopify POS Hub unique compared to the other POS solutions that are out there?

17:48You can basically plug in almost any USB peripheral into an iPad. And that's always where the problem has been. You can today, with the Android ecosystem, compatibility has always been better. But really the challenge has been with iOS. And most POS systems, as a result, most tablet-based POS systems have to rely on Bluetooth for this very reason. And so the hub is an Apple certified MFI device. So it plugs into the iPad and everything else plugs into the hub. Got it. And I mean, Fire Nation, you can obviously see why that's such a critical aspect to what you want to be doing in your business.

18:36And Ray, we kind of tease this a little bit. We haven't dived quite that deep into your partnership with Uber. So why don't you expand upon that a little bit? Shopify, in partnership with Uber, now offers fast, reliable local delivery from retail stores with Uber Direct. And that's powered by Uber's entire delivery network. What this means for our merchants is you can now easily connect Uber Direct to your Shopify online store and POS so that customers can choose one hour, same day, or scheduled delivery right at checkout when placing an online order. I mean, Fire Nation, that is an obvious game changer.

19:16So I kind of want to shift into one powerful move that our listeners should make right now after learning about Shopify edition in the POS hub, if they want, and of course they do, to stay ahead of the curve.

19:38sorry let me let me take that question yeah is this so wait is was the question if you're on Shopify POS what is the one powerful move to make yeah what's one powerful move they can make right now after learning about the Shopify edition in the POS hub to stay ahead of the curve For all of our merchants who care about reliability, which we think is most of our retailers and brick and mortar stores, we think that the hub is just a game changer. It moves peripheral reliability to 99.99 % reliability in terms of scanners, printers, all of that other stuff. It's like wired reliability. And it is going on sale at editions.

20:21We really encourage our existing customers to be amongst the first to get one of them. And you can buy it with all of the necessary peripherals you need to upgrade your hardware setup. Fire Nation, you are the average of the five people you spend the most time with. And you've been hanging out with RR and JLD today, so just keep up that heat. And for links to everything that we talked about, visit eofire.com, type Ray in the search bar, and the show notes page will pop right up. And of course, we'll have links to everything that Ray talked about, how you can get more information about everything that Shopify has going on.

20:56So I just want to say, Ray, thank you for sharing your truth, your knowledge, your value with Fire Nation today. For that, we salute you and we will catch you on the flip side. Thanks for having me on, John. Hey, Fire Nation, a huge thank you to our sponsors and Ray and Shopify for sponsoring today's episode. And Fire Nation, don't let another 90 day slip by. Inside the Freedom Circle, entrepreneurs are building real freedom with proven playbooks and community support. Claim your spot now at freedom-circle.com. This is my community. I'll catch you there or on the flip side. Are you ready for the ultimate all-in-one platform for entrepreneurs, marketers, coaches, and agencies?

21:35Build funnels, automate follow-ups, manage clients, and even white label your own software. Say hello to our featured partner, High Level, and visit highlevelfire.com to start your free trial today.