Not all shopping is created equal. And honestly, not all of it is fun.

Today I'm unpacking the tension between the idea of AI-powered shopping and the reality of how we actually shop today. While we love the experience of discovering products and making intentional choices, a huge portion of shopping — especially groceries — is repetitive, operational and tedious.

I explore where consumers are already signaling openness to AI assistance (hint: it’s not where you might think), and why the current tools still fall short of solving the real problem. From meal planning to managing the “messy middle” of grocery lists, I break down what’s missing, what’s coming, and why the future of agentic commerce may arrive faster than expected, once the technology finally catches up to demand.

This episode is sponsored by Mirakl Ads

Timeline

[00:00] – My daily cooking ritual and why grocery shopping is the least enjoyable part
[01:15] – The difference between “fun” shopping and repetitive shopping missions
[01:37] – What consumer behavior data reveals about how we actually shop
[02:15] – Where consumers are already comfortable letting AI step in
[03:00] – A real-world example of DIY grocery automation
[04:30] – Why current retail tools fail to solve the “messy middle” of shopping
[06:00] – The trust gap in grocery delivery (yes, even bananas matter!)
[08:30] – The real barrier to AI shopping adoption: technology, not psychology
[10:00] – Consumer attitudes toward AI agents completing purchases
[11:00] – What needs to happen before agentic commerce goes mainstream

Links & Resources

• Andrea K. Leigh's LinkedIn post about the grocery ordering browser extension she built
• Follow Andrea K. Leigh, Founder @ Allume Group, on LinkedIn
• Read my related articles:
  • Agentic Commerce Is a Sequencing Problem, Not an Existential One
  • Don’t Dance On The Grave Of Agentic Shopping Just Yet
  • How To Be Right About AI, And Still Lose
• I'm hosting a LIVE event with In-Store Marketplace and Catalyst Media Consulting on April 22 about In-Store Retail Media: are we measuring the wrong things? We'll discuss New Research on the state of in-store retail media measurement — and why the path forward may actually be simpler than the industry is making it. REGISTER HERE
• Subscribe to Retail Media Breakfast Club's daily newsletter
• Follow Kiri Masters on LinkedIn