Unlocking Customer Experience and Loyalty with Shopify POS UI: A Panel with Shopify, Clutch, and Endear

This is a transcript from a panel at Shoptalk in Las Vegas hosted by Koshi Samarasinghe from Shoptalk, Andy Odell from Clutch and Casey Drake from Endear.
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Koshi S: Hi, thank you for joining our workshop, Unlocking Customer Experience and Loyalty with Shopify POS UI. My name is Koshi Samarasinghe with Shopify, and I'm here today with two great partners. KC and Andy, would you introduce yourselves?

Andy O: Hello, yeah. I'm Andy O’Dell, founder and Chief Strategy Officer of Clutch. We've been building our integration for a while now, and I’m happy to share that it has just launched.

Casey D: I’m Casey Drake, VP of Sales at Endear. We built our business around the Shopify marketplace, so we’ve been integrated since day one. Endear is a CRM and clienteling tool.

Koshi S: Let’s dive into the retail landscape. What are the key trends you’re both seeing that retailers need to know about?

Andy O: The economy is a concern right now, so loyalty has become a major focus—across all verticals: fashion, grocery, food, convenience. The question is how to retain a customer longer and drive incrementality. The only way to do that is through individualization, which is a step beyond personalization. Just knowing someone is male isn’t enough anymore. We’re complex, motivated by different things. Brands need to understand those motivators and use them to craft better experiences. That’s the big trend for me.

Casey D: I’d say the biggest conversation is about AI. Everyone's trying to figure out how to use it, where it makes sense. What I’m seeing now is brands realizing that before AI can do anything meaningful, their data needs to be clean, centralized, and accessible. People are getting serious about establishing a single source of truth—a unified customer profile—because AI and personalization tools are only as good as the data they work with.

Koshi S: That’s a great point. So it’s really a shift from omnichannel to unified commerce. How are customer expectations changing the in-store experience?

Casey D: Since we focus on stores, I see this firsthand. Today’s customer knows that if they give you their email in one place, you should be able to connect the dots everywhere else. If you can’t do that, they lose trust and loyalty drops. The bar is low: just use the data you’ve collected. Don’t let me fill out a fit finder online and then act like you don’t know me when I walk into your store.

Andy O: Building on that, I’d argue we’re entering an experience-driven economy. Product, price, and location used to be enough, but now experience is the battleground. Younger generations expect seamless transitions between online and in-store. Loyalty isn’t just driven by programs anymore—it’s about reducing friction. Let me start a cart online and finish it in-store without restarting. That kind of ease builds LTV whether or not I’m in a loyalty program.

Casey D: Omnichannel and unified commerce aren’t the same. Unified commerce means it doesn’t matter where a transaction happens—it still counts toward your goal. Too often, brands claim to be omnichannel but incentivize store associates only for in-store sales. That creates weird friction. Tech can’t solve that. Brands have to set goals that reflect a unified customer journey.

Koshi S: So you're really talking about aligning goals and empowering associates to bridge the digital and physical.

Casey D: Exactly. One of my favorite examples is Shopify draft orders. It's such a simple way for an associate to make the sale count for them and still create a seamless experience for the customer.

Koshi S: Let’s pivot to Shopify technology. We build for the best merchant outcomes. Our platform is highly performant and extensible, and we’ve made that extensibility available through UI extensions. These let developers build native-feeling experiences directly in POS, leveraging our components and APIs. So when an associate wants to check loyalty points, it doesn’t feel like switching apps—it’s a seamless Shopify experience. Casey, you’ve been building with us from day one. Tell us what merchant pain points you’ve solved.

Casey D: One of the biggest hurdles in-store is that associates aren’t usually tech-savvy. Before POS extensions, they had to switch from Shopify POS to the Endear app—even on the same iPad, that was a barrier. Now, with our extension, they can click "send a message" right from the customer profile and text or email a customer instantly. It removes all excuses and makes adoption frictionless.

Koshi S: It's actually really fun. I was in the Alexis Guitar store, and the manager there was a former Nordstrom employee—a true legacy Nordstrom hire. She said to me, “Oh my God, using Endear is just like using an iPhone.” She loved how easy it was. Just click a button and everything works. That kind of ease of use, both for developers and brands, is what we’re striving for. Andy, I’m really excited to have you here because this is your first integration with Shopify. Why now, and what are brands saying to you about it?

Andy O: A lot of the challenges brands face in creating a unified experience come from trying to do it with legacy systems that weren’t built for this. There’s a major trend in vendor consolidation, tech simplification, and eliminating tech debt—which offers no ROI. It’s just expense. So when we were deciding who to partner with, we chose someone who truly understands that challenge and is building an open, flexible, yet streamlined platform.

It's the classic “one throat to choke” principle, and there’s value in that. When you piece together best-of-breed systems that don’t share a data structure or weren’t built to integrate, you multiply the very problems you’re trying to solve. Partnering with Shopify made perfect sense for us—it aligns with how we believe tech should be built: scalable, user-friendly, and designed to support both operations and marketing. At the end of the day, it’s about simplification.

Koshi S: I love that. Simplicity is always our north star. And we’re seeing merchants now flex their tech muscle by building custom apps, making Shopify part of their core tech stack. That ease of use creates flexibility.

I read something recently—trying to remember the exact quote—it was from the CTO of Tecovas. He said one of their mantras is “radical hospitality.” That phrase really stuck with me. It feels so relevant to customer experience and loyalty, because that’s what you want customers to feel. And the way you get there is what you mentioned earlier—through individualization. I’d love your thoughts on how unified data and data interoperability drive that.

Casey D: Honestly, I think it's the lifeblood of individualization. If your data isn’t unified, you’re stuck. Everything that’s happening with AI in retail right now hinges on clean, unified data. AI is only as smart as the information you feed it. And while AI can help clean up your data, the real power—the outputs, the actions—depends on having good data going in. So yes, it’s absolutely foundational.

Andy O: I completely agree. You can’t get to individualization without AI, automation, and active intelligence. That’s what makes one-to-one engagement possible. Whether you’re a brand or a consumer, we all want a better experience—one that feels like it's meant just for us.

There’s nothing more frustrating than getting an email from a brand you shop with regularly that clearly doesn’t understand you. I’m a guy, I buy men’s clothes—why are you sending me women’s shoes? That’s not even an AI problem. That’s basic segmentation. It’s a solvable issue, yet it still happens.

Casey D: Exactly. That’s not even an AI use case, that’s table stakes. You should be able to solve that without any fancy tech.

Andy O: Totally. But a lot of brands still miss it. I think part of the reason is change management. Everyone knows the car can drive itself now, but not everyone is ready to take their hands off the wheel. There’s still a lot of hesitation around letting AI lead fully.

Koshi S: So how is AI being used at Clutch today?

Andy O: We use AI across the board. We have active marketing intelligence, next-best-action recommendations for marketers, and with a single click, our platform automates all the campaign logic and deployment. We're trying to replace the old whiteboard-to-market process, which can take 8 to 12 weeks, with something that takes 30 minutes.

It's not just about creating better customer experiences. It’s also about making life easier for the marketer—freeing up their time to focus on strategy, not the mechanics of getting campaigns out the door.

Koshi S: Love that. Casey, from Endear’s perspective, how are you evolving the customer journey as expectations change?

Casey D: We focus on something really simple—making sure customers can talk to a real human at every stage. People think one-to-one communication isn’t scalable, but it is if you use automation smartly.

Just like in B2B sales, you use automation to initiate the conversation. When someone engages, that becomes a high-priority lead, and now you can bring in a real human to continue the dialogue. We focus on stores because store associates are uniquely positioned to do that. They have the time and the connection to make it work.

Koshi S: That visibility into app interactions and cross-channel data is huge, right?

Casey D: Exactly. The worst thing with some clienteling apps is when nobody actually uses them. We take a different approach: because we pull in the right data, we can tell associates exactly who to reach out to, what to say, and why it matters.

And honestly, in some cases, retail HQ should just go ahead and send the message on their behalf. We make that easy too—it still comes from the associate, but the heavy lifting is handled. It’s not the messaging that’s hard, it’s knowing who to message and why.

Koshi S: That’s something we hear all the time—brands want to simplify workflows so associates can focus on driving ROI.

Casey D: Totally. And with AI, we’re taking a “human in the loop” approach. Maybe one day we’ll fully take our hands off the wheel, but for now, AI is recommending what message to send, whether to send it at all, even correcting grammar and formatting. Those are small things, but they matter—especially with all the human error you get in store-level data.

Koshi S: Elevating the human experience through AI.

Casey D: Exactly. Making humans more powerful.

Koshi S: Let’s pivot slightly. Andy, since Clutch is launching a brand-new app, what kind of response have you gotten from brands so far? And how do you see merchants finding success with it?

Andy O: Sure. There’s a lot of data and KPIs showing that well-run loyalty programs directly impact the bottom line. It’s about increasing lifetime value, boosting basket size, reducing time between visits, and driving referrals. All of those have measurable ROI.

To summarize it, loyal customers spend about 250% more than non-loyal ones. But what’s interesting is how the concept of loyalty has evolved over the last five to seven years. We used to think of loyalty as spend-dollars-get-points, which convert to discounts. Now, if someone shops with you more than once, they’re considered loyal.

So the opportunity lies in bringing all the optimization—AI-guided actions, incremental spend drivers—to the other side of the enrollment wall. That’s where we can start influencing behavior in powerful ways. KPIs like lifetime value and average order value are significantly higher—60 to 70% higher—among loyal customers. When you scale that across hundreds of thousands of people, the impact is massive.

Casey D: We look at the same numbers. Endear’s impact is very much a long-tail effect. We may not bring in new customers right away, but we’re driving repeat visits and increasing order value over time. On average, we see a 52% increase in order frequency and a 70% increase in average order value for customers engaged through Endear.

What we’re really building with those one-on-one conversations is brand loyalty—the emotional kind. So when a brand opens a new store or makes an announcement, the customer feels like they’re winning. Like they discovered something special.

Koshi S: Right, it’s about resonating with how the customer sees themselves in the brand.

Casey D: Exactly. It sounds so simple, but if you’ve ever responded to a brand’s thank-you message—and then received a personal response back from a real associate asking what you liked—that’s the moment. Suddenly, you realize it’s not an automated message. You’re interacting with a human. That makes the brand feel different, memorable. You feel like you know someone there.

Koshi S: I love that idea of elevating the experience to be truly customer-serving. Are there any brand stories you’ve heard recently that you think are doing this well?

Andy O: One that stands out is Steve Madden. After the wildfires in L.A., they launched a campaign to distribute brand currency to people affected—so they could replace what they’d lost. That’s not just a loyalty move, that’s a human one.

They paused the commerce mindset and responded to people in crisis. Helping folks feel normal again—through something as simple as shopping—was a beautiful example of both transactional and emotional loyalty. It was generous, timely, and deeply empathetic. And it really drives home what loyalty should be about: connection, recognition, and meaningful service.

Koshi S: That’s a great story.

Casey D: I’ve got one too. Billy Reid is a great example of a brand using Endear in a way that’s fully integrated and thoughtful. They’ve been beta testing our appointment scheduling feature, which we’re officially launching soon.

What they’ve done is simple but smart—you go to their website, pick a store, see the team members there, and schedule an appointment to meet with someone. That’s personalization at the associate level. They’ve taken Endear and woven it directly into their brand’s operations. Their usage of the platform is among the best we’ve seen.

Koshi S: That’s such a clear differentiator. I’ve had a completely different experience recently trying to book an appointment with a brand. I filled out a long form, and then four different people contacted me, each with a different (and incorrect) understanding of my needs. That disconnect between customer, data, and associate is so obvious when it’s broken.

Casey D: Yeah, we’re actually working on a store check-in process at Endear. The idea is to track visits, not just purchases. One of our co-founders visited a store that had a great check-in process—but there was no follow-up. It made a strong first impression, but nothing came of it.

We want to solve that. If someone checks in, there should be an automatic follow-up. It should be seamless. Customers shouldn’t fall through the cracks.

Koshi S: That’s a fantastic idea. Andy, as Clutch gears up for launch, what’s the response been like from merchants? Are they excited about the Shopify integration?

Andy O: Absolutely. We have a very active pipeline of brands who are eager to understand what new capabilities this opens up. It really meets the expectations of mid-market and enterprise brands looking for flexibility, speed, ease of use, and quick time-to-value. This is the right time for the partnership, and the energy isn’t just on our side—the market is definitely responding.

Koshi S: We’re thrilled about it too. Before we wrap up, I’d love to hear from both of you: what excites you most about how our combined solutions are future-proofing retail? What’s the next innovation you see coming?

Casey D: I feel like I’m on repeat, but I’m really excited about what AI is going to unlock. If I were starting a brand today, I’d build it on Shopify. The ability to plug in best-in-class vendors like Endear is a game-changer.

Legacy systems and messy data are what slow most brands down. If you avoid that from day one, you’re setting yourself up to capitalize on AI and every innovation that follows. When the car is ready to drive itself, you’ll actually be able to let it.

Andy O: Shopify feels to me like it was built with a European engineering mindset—efficient, scalable, practical. Those are critical for long-term success.

Looking ahead, I think we’re moving toward a future where we don’t have five million loyalty program members—we have five million unique loyalty programs. One for each person. Their preferences, behaviors, and even their seasonal habits all inform the experience. AI picks up on those nuances and executes the right strategy at the right time.

That’s when the brand gets what it wants—loyalty, revenue, retention—and the customer gets what they want: relevance, ease, and a meaningful connection.

Casey D: That resonates. One thing we’re focused on now is capturing more of the in-store experience. So much happens during a store visit, but it’s hard to document. We’re building a new AI note taker for that exact purpose.

Let’s say I meet you in-store, and after our interaction I quickly record, “Just saw Koshi, she loved the new blazer. Follow up in a week.” The AI reads that, recommends a follow-up, logs the interest, and feeds that back into the marketing and sales systems.

That’s data we’ve never had access to in a structured way before. Now it becomes part of the whole ecosystem. It’s another piece of the puzzle that helps us individualize every touchpoint.

Koshi S: That’s brilliant. Well, I think we’re just about at time. Thank you both—Andy, Casey—for being amazing partners and sharing your insights today. We’re so excited about what we’re building together.