The AI First Holiday Edition
The 2025 holiday season is giving us a front-row seat to the future of retail. In this edition, we’ll highlight the AI breakthroughs that just shaped the biggest shopping week of the year, and what they tell us about where innovation is headed in 2026.
What’s Inside:
Five Flavors of AI Shopping
Holiday Shopping + AI
Key Stats this Holiday Season
Holiday Ads Brought to Life with AI
5 Flavors of AI Shopping
Nearly 9 in 10 retailers are weaving AI into the shopping experience, and conversational systems are on track to save $80B in support costs by 2026. From subtle recommendations to fully autonomous shopping agents, five core types of AI are reshaping how we shop and how retailers sell:
Reactive AI — Quick responders that instantly answer prompts or questions. Think chatbots and support agents replying to “Where’s my order?” in seconds.
Limited-Memory AI — Learners that use past behavior to personalize future experiences. Think Amazon’s recommendation engine curating products based on your browsing and buying history.
Theory-of-Mind AI — Empathetic engines that interpret tone, intent, and urgency. Think Assistants that understand “Need this gift by Friday” and prioritize shipping options.
Self-Aware AI — Although still being perfected, this is AI that deeply understands your long-term goals, tastes, and routines.
Agentic AI — Autonomous helper that plans, reasons, and acts on your behalf. Think digital shoppers that hunt, compare, buy, and even negotiate deals while you sleep.
Together, these five “flavors” are fueling one of the biggest transformations retail has ever seen.
An AI First Challenge: As you reflect on your shopping this season, can you spot which “AI flavor” is behind your favorite retailer’s magic moment?
Holiday Shopping + AI News
Here are some of the most exciting AI-powered tools and experiences we saw emerge this holiday shopping season:
Google’s AI Now Calls Stores
Flavor: Agentic AI
Google’s conversational shopping agent will now call stores to confirm what’s available before you head out to purchase. It plans, reasons, and acts — all on your behalf. (Read more in Retail Dive)
Amazon “Buy For Me” Agent
Flavor: Agentic + Limited-Memory AI
Amazon’s newest assistant can now purchase off-Amazon products for you, using what it already knows about your preferences. It’s your tireless, cross-retailer shopping elf, comparing, buying, and saving you time without you lifting a finger.
OpenAI’s “Deep Research” Shopping
Flavor: Limited-Memory + Theory-of-Mind AI
OpenAI quietly rolled out a commerce-focused assistant that helps users compare products, summarize reviews, and build gift lists in a single conversation. It learns from your cues and understands context, bridging logic with intuition for a smarter shopping experience.
Lowe’s Mylow Enters Elf Mode
Flavor: Agentic + Reactive AI
Mylow, Lowe’s OpenAI-powered home improvement assistant, answered nearly 1M questions this season. It also doubled online conversion rates and was highlighted in Q3 earnings, proof that AI can boost both cheer and sales.
AI’s Breakout Moment: Key Stats From the Biggest Week in Retail
Cyber Monday: $14.25B (+7.1% YoY) — biggest online shopping day ever
Cyber Week: $44.2B (+7.7% YoY)
Black Friday: $11.8B (+9.1% YoY), outpacing Cyber Monday for the second year in a row
AI’s Impact
AI-driven traffic to retail sites surged 670% on Cyber Monday
Season-to-date AI traffic is up 760%
Agentic AI influenced 20% of global online orders, driving $67B in sales
How Shoppers Used AI
62% used AI tools or chat assistants for holiday tasks
37% used AI to check inventory, pricing, or availability
44% used AI for gift ideas or product comparisons
Bottom line: This was the first holiday season where AI shaped shopping end to end — from discovery to decision to purchase.
AI-Generated Holiday Ads
As AI shows up across the entire shopping journey, it’s also reshaping how brands tell their stories, holiday ads included.
For nearly two decades, John Lewis has set the standard for heartfelt holiday storytelling. This year, they embraced AI-assisted production to refine color, continuity, and composition, while keeping the emotional core unmistakably human.
The result? A visually stunning, unmistakably John Lewis story built around a simple act of kindness, a moving soundtrack, and a signature tear-jerker ending.
From All of Us at Forum3
As the season of gratitude, giving, and connection is here, we’re wishing you time well spent with family, friends, and your teams.
Here’s to a joyful holiday season, and to the stories, insights, and AI breakthroughs we’ll create together in 2026.
Happy Holidays!
Stay Curious. Stay AI-First.
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