Recommending the wrong whiskey to a loyal customer does not just miss a sale. It breaks trust, and once trust breaks, no amount of personalization copy fixes it. Recorded live at K:LDN 2026 in London, this conversation is about the thing every brand now has in common. Everyone has access to the same AI tools. So what actually separates the brands winning with them from the ones just using them? Phillip Jackson sits down with Jake Cohen, VP of Insights at Klaviyo, and Tim Martin-Harvey, Head of Ecommerce at The Bottle Club, a UK multi-brand alcohol retailer carrying roughly 9,500 products. Their answer: memory. Not the AI kind, the brand kind… meaning the stored, structured context a business builds about its own customers and products over time. Tim explains how one mandatory checkout question, asking whether an order is a gift, for self-consumption, for hosting, or for trade, reshaped his customer insight and exposed why standard RFM and lifetime value metrics break down across different buyer types. Jake widens the lens, arguing that loyalty is better measured through engagement across touchpoints than through money spent, and that the brands seeing real gains from AI are the ones writing customer and product knowledge down as reusable context, what Klaviyo calls "artifacts." The conversation gets specific fast, down to the exact wrong recommendation that can cost a brand its credibility, and closes with Jake's straightforward plan for putting this into practice over the next 90 days. What you'll learn Why context, not performance marketing spend, is becoming the real competitive moat as every brand adopts the same AI toolsHow one checkout question corrected years of wrong assumptions about who buys and why at The Bottle ClubWhy standard RFM and lifetime value segmentation breaks down once you separate gift buyers from self-consumption buyersWhy loyalty is better read through engagement than through total spendThe exact kind of recommendation mistake that destroys customer trust, and how layered product data prevents itJake Cohen's 30/60/90 day plan for building AI context that compounds over time Key takeaways As every brand uses the same AI tools, the real differentiator becomes stored context, meaning written detail about the brand, the customer, and the products, what Klaviyo calls "artifacts."The Bottle Club added one mandatory checkout question (gift, self-consumption, hosting, or trade), which corrected wrong assumptions about which products are gifts and showed that standard RFM and lifetime value metrics break down across different buyer types.Loyalty reads better through engagement across touchpoints than through money spent. The goal is asking the right questions instead of pushing a discount, then building context on each customer over time.Recommendations get dramatically stronger when product data (margin, weeks of cover, gift versus self-consumption, category nuance) is layered onto customer data. Recommend a Jack Daniels to a lifelong Jameson drinker and you have made, in Tim's own framing, the worst recommendation possible, one that costs more than the sale.Jake's plan: set up a service agent and build its skills first, then use Composer to explore your data and test ideas, then keep improving the skills as you learn, since the value compounds over time. Pull quotes "The word of the moment to me is actually context, and that context, if you can store it effectively and leverage it effectively, is the way that you can create a moat, because you can serve more people more personally, more memorably, which will create deeper relationships and, of course, more durable business over time." — Jake Cohen, VP of Insights, Klaviyo [2:08 to 3:04] "What starts to become very important in the world of AI post LLMs is that the most important thing a brand can do is show up for someone the way that they need when they need it." — Jake Cohen [9:09] "I genuinely think Klaviyo agent makes the most sense to be the agentic storefront, and that's not just me Klaviyo championing it. It's genuinely got the most context from multiple sources." — Tim Martin-Harvey, Head of Ecommerce, The Bottle Club [18:49 to 19:48] "The answer should not be, 'Great, here's 10% off, go buy one.' The answer should be, 'How long are you running? Do you have a color you're interested in? Do you have a race coming up?' As you start to collect that information, that helps build the context for that individual, and they become the type of customer that will stay with you for a lifetime." — Jake Cohen [10:26] Chapters 0:00 Cold open and introductions4:45 Memory is the new moat, why context beats tools8:00 The checkout question that rewrote The Bottle Club's customer data9:15 Why RFM analysis breaks down across buyer types10:40 Showing up for the customer the way they need, when they need it12:15 The running shoe example, questions over discounts19:08 The whiskey mistake, the worst recommendation in retail20:38 Why ...
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