The CX leaders behind HOKA, UGG, and Bombas. Learn what's next for AI in retail.
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Welcome to the 3,912 new operators who joined us this week! 🤯
Hey there, Insiders 👋
Thank you for being here. I say that a lot, and I mean it more every week. This community keeps growing because you keep sharing what works, asking the hard questions, and holding each other (and me) to a higher standard. That means everything.
This week, one theme kept surfacing across every piece of content I pulled together: your data layer is now your most important competitive asset.
❌ Not your creative.
❌ Not your ad budget.
❌ Not your tech stack.
The invisible infrastructure underneath all of it.
Sean Larkin (founder of Fueled, now Chief Product Officer at OpenSend) sat down with me to break down why your tracking is quietly degrading and what the brands recovering 20 to 30% more attributed conversions are doing differently.
The Knowledge Drops unpack why AI shopping agents are skipping your products entirely and what "agent ready" actually looks like at your specific revenue stage. And the Industry Pulse this week? Juniper Research just put a $1.5 trillion number on agentic commerce by 2030, Stripe's Shoptalk debrief confirmed discovery has already shifted to AI surfaces, and Klaviyo shipped its biggest product release ever.
Whether you're doing $30K months or $2M months, the brands that get their data foundation right this year will be the ones everyone else is trying to reverse engineer 18 months from now.
Here's what's inside this week's edition:
🎧 Podcast Release – Your ROAS looks fine. Your tracking is broken. Sean Larkin reveals what's hiding under the hood of your ad attribution.
💡 Knowledge Drops – Why AI agents are skipping your products, and the new customer your store was never built to serve.
🔥 Tool of the Week – Littledata: the server side tracking layer your ad platforms are starving for.
📡 Industry Pulse – $1.5 trillion agentic commerce forecast, Stripe's Shoptalk debrief, Klaviyo's Composer launch, and ShipMonk's apparel play.
🎤 Gladly Connect Live 2026 – What's ahead for customer experience this year.
Let's get into it. 👇
🔥 AI Is Already Shopping For You 🔥
Meet the CX leaders building what’s next in retail
AI isn’t just changing how brands handle support, it’s changing how customers shop, discover, and buy. At Gladly Connect Live, May 4–6 in Atlanta, CX leaders from HOKA, Deckers, UGG, Crate & Barrel, and Bombas will dig into what that actually means for their businesses.
The anchor session for Shopify brands: a Day 3 panel on agentic commerce, where CTOs and CDOs from leading retail brands tackle how AI agents are starting to shop on behalf of customers, and how brands show up when ChatGPT or Perplexity becomes the discovery channel instead of Google.
You'll hear from the teams behind The Black Tux, Ollie, Pact, Condé Nast, StockX, and Smith Optics, practitioners who have actually shipped AI in production, not just talked about it.
This event sells out. Save your seat before it's gone on Gladly.ai
[ Sign Up Now ]
🎧 New Podcast Episode! 🎧
Your ROAS Is Fine. Your Tracking Is Broken.
You're staring at your dashboards on a Tuesday morning. Meta says 94 conversions. Google insists it's 67. Shopify shows 83. Same period, three different realities, and every budget decision you make is riding on which number you believe.
I sat down with Sean Larkin, Chief Product Officer at OpenSend and founder of Fueled, to dig into what's actually happening under the hood. After years of rebuilding analytics infrastructure for scaling Shopify brands, he keeps seeing the same pattern: browser pixels are quietly dying, and most brands have no idea how much conversion signal they're already losing.
Here's what we unpacked:
Browser pixels are structurally losing signal every year Apple's privacy updates keep shrinking your attribution window while ad blockers silently intercept the tracking calls your ad platforms depend on. The numbers still update, but the data underneath has been degrading since 2017.
One app install can silently tank your ad performance Sean shared a scenario most operators never think about, and the damage window is longer than you'd expect.
The ROAS lift hiding in your data infrastructure Brands making one specific infrastructure shift are seeing 20 to 30% more attributed conversions on Meta without changing a single ad. Sean breaks down exactly why.
Why enterprise CDPs might be overkill for your stage There's a growing conversation about what mid market brands actually need versus what they're being sold. Sean's perspective (as a former Segment certified engineer) is worth hearing.
The new blind spots most brands don't even know exist ChatGPT assisted checkout, Shop Pay routing, AI driven purchase flows: these create conversion gaps that browser pixels will never see.
If you're spending $5K to $500K a month on paid acquisition, this conversation could change how you allocate your next budget cycle.
LISTEN NOW → Get the server-side tracking framework before your next budget call
💡 Knowledge Drops of the Week 💡
The Silent Reason AI Keeps Skipping Your Products
Most merchants think they have a technology problem. They don't. They have a data problem wearing a technology costume.
Right now, AI shopping agents like ChatGPT, Google AI Mode, and Perplexity are evaluating your catalog in milliseconds. If they can't instantly answer basic product questions (is it waterproof? is it vegan? does the sizing run small?), they don't wait around. They send the customer to a competitor whose data answers those questions without hesitation.
Here's what's working right now:
Attribute depth beats marketing copy The brand story that converts humans does nothing for an AI agent that needs structured facts. The article breaks down exactly how many fields your hero SKUs need and which ones matter most.
Your internal AI tools are choking on the same problem That support chatbot underperforming? That inventory agent misfiring? There's a single root cause most merchants never connect to their external visibility issues.
The first mover window is real, but it's not forever Morgan Stanley pegs US agentic commerce at $385 billion by 2030. The merchants who clean their data layer now will own recommendation surface area that gets exponentially more expensive to compete for later.
If you're doing $30K to $2M per month, this is the most actionable 15-minute read you'll find this week.
[ READ THE FULL BREAKDOWN ] - The step-by-step data hygiene playbook for Shopify merchants in the age of AI
The New Customer You’ll Never See (But Can’t Afford to Ignore)
For 20 years, every decision you made about your Shopify store was built for one customer: the human who browses, hesitates, and (too often) abandons. That assumption just broke.
AI-attributed orders on Shopify are up 11x, and AI-referred traffic is up 7x since early 2025. This second customer evaluates your store in a completely different way. The human feels your brand story. The AI agent reads your data attributes. The human reacts to urgency. The agent ignores it. The human might give you a second chance. The agent moves on in milliseconds.
Here's what's working right now:
There are three models for how AI "shops" your store Not all agent interactions work the same way, and the model that matters most for mid market Shopify merchants right now is probably not the one getting the most LinkedIn buzz. The article maps all three and shows which one is your easiest entry point.
The premature complexity trap is burning brands at the $500K to $2M stage There's a specific sequence that separates brands compounding AI performance from brands leaking it. Get the order wrong and every tool you add makes things worse, not better.
"Agent ready" looks different at every revenue stage What a $10K per month store should prioritize this week is not the same as what a $2M per month operation needs to fix. The article breaks down the exact moves by stage so you're not over building or under preparing.
This is the strategic companion to the data hygiene playbook above. One gives you the "why now" framework. The other gives you the audit checklist.
[ READ THE FULL BREAKDOWN ] - The two customer framework every Shopify merchant needs to understand in 2026
🔥 Tool of the Week 🔥
Your Shopify store had 100 orders yesterday. Google Analytics only saw 80 of them.
That's not a hypothetical — the average DTC brand is missing 20–30% of transaction data in GA4 right now. Ad blockers, iOS privacy restrictions, Shop Pay redirects, and subscription renewals all silently break Shopify's default tracking. The result? Your ROAS looks worse than it actually is, Meta and Google's algorithms optimize against incomplete data, and you end up killing profitable campaigns you should be scaling.
Littledata is the server-side data layer that fixes this in about 10 minutes — no GTM, no code, no developer. It connects your Shopify store directly to Google Analytics, Google Ads, Meta Conversions API, Klaviyo, and more, capturing every conversion that browser-based tracking misses. Over 2,000 Shopify brands trust it as the foundation for their marketing decisions.
If you're spending on paid acquisition and making decisions from GA4 reports, you need to know whether your data is lying to you first.
👉 Run Littledata's Free Conversion Checker → See exactly how many orders your GA4 is missing — takes 30 seconds
⚡ This Week’s Industry Pulse ⚡
A handful of updates land that actually move the needle. Here's what made the cut…
Juniper Research published the first comprehensive market forecast for AI agent driven shopping, projecting total transaction value rising from $8 billion in 2026 to $1.5 trillion by 2030. Mastercard, Visa, and Stripe were named the leading payments infrastructure providers positioning for this shift. Trust remains the top barrier to adoption, and the research confirms agentic commerce will complement traditional checkout rather than replace it. The window to build your data layer is now.
Stripe's post Shoptalk analysis captures where agentic commerce actually stands today: Meta's new in ad checkout flow built on the Agentic Commerce Protocol, Sephora using loyalty data inside ChatGPT for personalized recommendations, and broad retailer consensus that discovery has already shifted to AI surfaces. The most honest theme across 10,000+ commerce leaders? The gap between "we see it happening" and "we have a plan."
Klaviyo shipped its biggest Q1 ever, headlined by Composer: an AI tool that generates complete campaigns from a single prompt, including audience segments, copy, and send logic, all trained on 14 years of performance data from 193,000 brands. The release also adds Customer Agent skills for order tracking, returns, subscription edits, and loyalty lookups, pushing Klaviyo deeper into agentic territory for both marketing and service. Currently in private beta.
ShipMonk launched its first category specific 3PL facility in Louisville: 406,000 square feet purpose built for apparel brands with dedicated rework stations, an in house returns grading program, and on site embroidery services. The returns first design directly targets the operational pain point that costs apparel merchants the most margin.
Until Next Thursday
I didn't plan it this way, but every section this week landed on the same conclusion.
Sean Larkin showed us that the tracking data powering your ad spend has been quietly degrading for years. The knowledge drops laid out why AI shopping agents are skipping your products and what "agent ready" actually looks like at your revenue stage. And the industry pulse? Juniper Research just put a $1.5 trillion number on agentic commerce by 2030, Stripe confirmed that discovery has already shifted to AI surfaces, and Klaviyo is building agents that run on your customer data.
The brands that win the next 18 months won't be the ones with the biggest ad budgets or the flashiest creative. They'll be the ones who got their data infrastructure right while everyone else was still debating whether this shift was real.
Pick one thing from today's edition. Audit your top 20 product attributes. Ask your team when you last checked your pixel health. Look at whether your store answers the questions an AI agent would ask. Start there. The compound advantage builds faster than you think.
If something in today's edition clicked, or you're already making moves on your data layer, hit reply. I read every response, and these conversations shape what we dig into next.
Keep building.
Cheers!
— Steve
P.S. Missed a previous edition? Check out the archive for more growth strategies and insights.
