Your Daily Retail Brief

Friday May 29, 2026

Hey Friends,

Friday is here and what a week it has been. This week felt like another major turning point in how AI is reshaping retail, and the data is starting to back up what a lot of the industry has been predicting. Adobe reported that AI-driven traffic to retail websites jumped nearly 400% year over year, but the bigger story is that those shoppers are actually converting at higher rates and spending more time on-site than traditional traffic sources. In other words, consumers are no longer just experimenting with AI for product discovery, they’re actively shopping through it. At the same time, strong earnings from retailers like Best Buy, Kohl’s, and Dollar Tree showed that companies leaning into retail media, data, automation, and smarter customer engagement strategies are finding real momentum in a pretty unpredictable market.

There’s also a growing split happening across retail right now. Value-focused chains continue to expand aggressively, luxury brands are doubling down on big experiential bets like Vancouver’s new Oakridge Park development, and legacy department stores are still trying to stabilize after years of pressure. The common thread through almost every story this week: retailers that are adapting quickly to changing consumer behavior and new technology trends are putting themselves in a much stronger position heading into the second half of the year.

Let’s get into it……