Loyalty isn’t a punch card anymore, and it definitely isn’t just repeat purchases. We’re chasing a tougher standard: loyalty of choice. That’s the kind of customer loyalty that shows up when someone sticks with you even when a competitor is cheaper, closer, faster, or simply more convenient and when they come back after you’ve had a service failure or a product miss. I’m joined by Jaclyn Wands, VP of Product and AI at Phaedon, to get concrete about what “true loyalty” looks like in 2026 and how to measure it without fooling ourselves.
We break down the difference between transactional loyalty (habit, ease, familiarity) and emotional loyalty (preference, trust, forgiveness). Jacqueline shares practical examples from travel and hospitality, including a smarter approach to airline loyalty programs: stop blasting generic promotions and start using data to solve the customer’s problem with relevance and timing. We also tackle the uncomfortable truth about personalization. If it feels like customers are being “haunted,” it’s usually because the brand is optimizing for its own KPIs, not the customer experience.
Then we go deep on AI in loyalty and marketing. AI can create massive efficiency, but it also exposes structural problems in your data ecosystem and processes because it scales whatever you already have. Jaclyn lays out a clear “human in the loop” philosophy, what AI should absolutely handle (repetitive work, zero-to-one drafts), and where humans must stay accountable. Finally, we look ahead to AI assistants as a new gatekeeper for discovery and booking, and why brands may need loyalty programs connected into AI marketplaces to stay visible and differentiated.
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