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Winning The Checkout: Real-World eCommerce Fixes that Convert Customers and Build Loyalty

Welcome to eCommerce Fastlane! As Q4 ramps up, Shopify brands face mounting challenges: acquisition costs are climbing, and customer expectations keep rising.

How do you keep growing—in conversions, loyalty, and lifetime value—without getting bogged down by AI hype or generic advice?

Today, I’m joined by Greg Tull, Director of Marketing at Classy Llama. With nearly two decades of eCommerce expertise, Greg’s team is all about practical wins—grounded, data-driven strategies and real-world customer experience solutions for scaling on Shopify Plus.

Whether you’re gearing up for BFCM or just looking to build stronger customer relationships this season, you’ll discover simple, actionable ways to harness AI, design friction-free journeys, and deepen loyalty beyond the first sale. Let’s dive in.

What You’ll Learn

✅  How practical AI delivers real wins for Shopify stores—not just hype, but measurable results like increased AOV, efficient support with smart bots, and ongoing ROI tracking through A/B testing.

✅  Ways to optimize mobile user experience—cut navigation friction, use thumb-friendly layouts, and make add-to-cart buttons, variant pickers, and delivery details visible at every step.

✅  Unlocking advanced filtering for big catalogs—see how new AI (including Retrieval Augmented Generation) personalizes product recommendations based on intent and context, not just data points.

✅  Making upsells and cross-sells work—discover how relevance boosts order size, with in-cart and post-purchase offers that delight (not distract) the shopper.

✅  Why actionable analytics truly fuel growth—master the art of clean, meaningful dashboards that power decisions for both fast-moving DTC brands and larger enterprise merchants.

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Episode Summary

In this episode, Steve sits down with Greg Tall from Classy Llama to cut through the Q4 noise and talk about what actually moves the needle for Shopify brands year-round. With customer acquisition costs climbing and everyone scrambling for their slice of holiday spending, it’s tempting to throw more budget at ads or chase the latest tech trend. But Greg and Steve take a different approach—they dig into the fundamentals that create lasting competitive advantage.

The conversation covers practical territory: how to audit mobile experiences with a simple thumb test, when AI actually delivers ROI (and when it’s just expensive clutter), and why loyalty programs aren’t just nice-to-haves anymore—they’re essential for building the kind of customer relationships that survive beyond Black Friday. Greg brings real-world examples from the agency trenches, from handling 625,000-SKU catalogs to explaining why pop-ups are universally hated (even by marketers).

This isn’t about quick fixes or seasonal hacks. It’s about designing an experience where decisions feel effortless, where first-time buyers naturally become repeat customers, and where the data actually tells the story of what’s working. Whether managing a growing DTC brand or scaling a B2B operation, the message is clear: UX isn’t a project—it’s an ongoing practice, and the brands that treat it that way are the ones that thrive in every market cycle.

Strategic Takeaways

👉 Treat user experience as a living, breathing effort. Schedule regular mobile audits, track conversion clues, and run small experiments—your site should always be evolving, never “done.”

👉 Make buying on mobile easy—cut out taps, pop-ups, and hidden info. Give shoppers what they need to decide fast so the path to purchase feels natural.

👉 Lean into loyalty and rewards. Programs and gamified touches create sticky customer bonds that drive repeat sales and make lasting impressions, even when the competition is fierce.

👉 Create B2B experiences that feel as personal as DTC. Let business customers self-serve, get instant quotes, and manage orders online—today’s buyers expect B2C simplicity, even at work.

👉 Get serious about data from day one. With clean tracking and smart AI analysis, brands can experiment confidently, market smarter, and avoid expensive guesswork down the road.

Guest Spotlight

Greg Tull
Director of Marketing, Classy Llama

Greg leads the marketing charge at Classy Llama, an agency known for challenging the status quo in eCommerce. With a foundation in Magento and a refined focus on Shopify Plus, Greg and his team are all about taking stores from “good enough” to best-in-class. They specialize in practical growth—delivering everything from AI-driven personalization and robust data lakes to hands-on conversion optimization for DTC and B2B brands alike. With hundreds of high-performing stores under their belt, Greg’s leadership pushes brands to rethink user experience and make every digital touchpoint count.

Links & Resources

Thanks for Supporting the Pod!

Over the past eight seasons, I’ve been incredibly lucky to chat with some of the brightest founders in ecommerce building remarkable Shopify brands and partners shaping the app and marketing ecosystem. Honestly, every conversation has taught me something new, and I’m grateful for the chance to learn alongside you.

What matters most is that this podcast helps you solve real challenges and unlock new growth for your business. Your support, feedback, and stories have made this journey truly special. Thanks for tuning in, sharing your wins and losses, and being part of the eCommerce Fastlane community.

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