GTM & Marketplace Leader @ Claim | Investor & Advisor | 📝 Write about tech x culture | Ex-Warriors, 49ers
Main Street, 1985: The corner store clerk knows your name and your Tuesday Coca-Cola fix is waiting for you when you walk in. No data lakes, just memory and genuine care. As operators, how do we build for this experience with all this pressure to implement AI? Fast-forward to 2025. Foot traffic has moved online, loyalty stacks have exploded, and AI promises that same sixth-sense hospitality at hyperscale… but usually it still feels like a spreadsheet wearing a name tag. Where AI is already adding delight today: ☕ Starbucks: Deep Brew blends weather + daypart + order history - Frappuccinos on a scorcher, Pumpkin Cream Cold Brew when the SF fog rolls in. 🔺 McDonald’s: They bought, integrated and sold Dynamic Yield to flip drive-thru menus in real time (rain = more McCafé). 🍕 Domino’s ANZ: DOM Pizza Checker computer vision has inspected 50M+ pizzas, catching quality issues before the pies hit the box. Where AI kind of sucks right now: 🤷 The black box problem: Predicts what, rarely why - and why is where hospitality lives. Creepy over-personalization: one mistimed ping trained on too much data goes helpful into stalker-y very fast 🚰 Data flows one way: the brand “knows” me, but I don’t feel known and usually can't wait in Here's what I want to see more of from merchants and brands: 1️⃣ Humanizing the handshake. Kick off new-user flows or product intros with a 10-second voice note from the founder or CEO. Low lift, high warmth. 2️⃣ Letting data pick the moment, letting people pick the words to keep your brand standing out. Algorithms trigger when; your team writes copy that still sounds like you. Even you personalize with AI, let people deliver the foundations. 3️⃣ Closing the loop offline. Train staff to reference digital touchpoints IRL (“Saw your DM and your first purchase anniversary in the app - dessert’s on us”). As we pipe real-time purchase data into surprise-and-delight rewards, the secret sauce remains - AI and ML does the math, humans deliver the magic and create the loyalty.