Recorded live at RetailClub AI Festival, a few hours after Diptendu joined Ricardo Belmar on the PCH Stage for a session called You Can't Automate What You Don't Understand. Ricardo and Casey Golden pick up where that session left off.
Diptendu explains why every stakeholder builds their own version of a process, which retail data is usually clean and which is a mess, and why a year-long data cleanup for its own sake is probably never feasible for an AI automation project. Casey asks about the people side of AI automation, and Diptendu names the shortcut culture that trades long-term strategy for deadlines. Ricardo asks how to measure AI efficiency beyond cost reduction, and Diptendu's answer is the mic drop: at Giant Tiger, AI efficiency starts with moving inventory faster, and the hours AI saves won't reach the bottom line unless you redirect them. If AI efficiency is on your 2027 plan, watch this one.
This is one of eight episodes recorded live at RetailClub AI Festival, coming to all our shows on the Retail Razor Podcast Network.
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*Retail Agent Con - November 17, 2026*
Explore how AI agents fit into retail work at Retail Agent Con, a live virtual event on November 17, 2026, from 11 a.m. to 3 p.m. Eastern, produced by IHL Group with ClearSight AI.
Join retail leaders like Glenn Allison of Tractor Supply, Scott Saeger of David’s Bridal and Justin Emig of Artisan Lane Furniture, Dr. Janet Sherlock on the organizational changes required for agents and humans to work together, analysts like Greg Buzek and Jerry Sheldon of IHL Group and Retail Razor’s Ricardo Belmar, for practical conversations about agents in merchandising, order management, inventory control, store systems, and more.
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*Retail Razor Show S6:E16*
*Released on November 10, 2026*
*Guest info*
*Diptendu Ray.* https://www.linkedin.com/in/diptenduray/
_Head of Product Management & Head of AI,_ *Giant Tiger.* https://www.gianttiger.com
Diptendu Ray is a product and AI leader who has spent over a decade building products that solve real business problems. From writing code early in his career to leading product teams and digital transformations, he has worked across retail, eCommerce, SaaS, and health insurance. Along the way, he has managed products generating over $4 billion in revenue and helped drive more than $300 million in incremental sales at companies like Yahoo!, Humana and Staples. He currently works at Giant Tiger as Head of Product Management & AI.
His experience with AI goes back over 12 years, spanning personalization, machine learning, automation, and conversational AI. He was recognized among Signifyd’s 30 Most Influential in eCommerce in 2024 and named a Top AI Leader by Rethink Retail for 2027.
*Chapters*
00:00 Teaser
00:34 Show Intro
04:15 AI Automation's Hidden Traps (Giant Tiger)
05:04 Your Documented Process Is Probably Fiction
08:21 Why Retail's Data Is a Dumpster Fire (and the Fix)
12:24 The Shortcut Culture That Kills AI Projects
13:36 AI Efficiency Isn't Cost Cutting: The Mic Drop
15:58 Show Close
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