Giant Tiger's Head of AI Diptendu Ray on mapping the process your teams follow, fixing retail data one project at a time, and putting AI automation to work. 

Interview 15 people about how a process works, and you could get 15 different versions. Diptendu Ray, Head of Product Management and Head of AI at Giant Tiger, says that's where AI automation starts: finding what those versions have in common.

Ricardo Belmar and Casey Golden recorded this one live at RetailClub AI Festival in Huntington Beach, a few hours after Diptendu joined Ricardo on the PCH Stage for a session called You Can't Automate What You Don't Understand. They pick up where that session left off, with the parts of an AI automation project nobody plans for and what AI efficiency should mean for a retailer. This is Season 6, episode 16.

In This Episode, You'll Learn:

• Why every stakeholder builds their own version of a process to hit their own KPIs.
• How to find the common ground when 15 people give you 15 different answers.
• What a chicken curry recipe has to do with process drift (jump to 07:01).
• Which retail data is usually clean, and which data is a mess.
• Why Diptendu says a year-long data cleanup for its own sake is probably never feasible.
• How Giant Tiger handles privacy and security for customer and payments data (jump to 11:16).
• How deadline shortcuts trade long-term strategy for short-term gains.
• Why Diptendu's first AI efficiency goal at Giant Tiger, faster inventory turns, has nothing to do with headcount.
• Why the hours AI automation saves your team won't reach the bottom line until you put them to work.

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This is one of eight episodes we recorded live at RetailClub AI Festival, rolling out across all four shows on the Retail Razor Podcast Network. Subscribe so you catch every one!

Featured guest.

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

Meet your hosts.

Helping you cut through the clutter in retail & retail tech:

Ricardo Belmar is an NRF Top Retail Voice for 2025 and a RETHINK Retail Top Retail Expert from 2021 – 2026 and a Top AI Leader for 2027. Thinkers 360 has named him a Top 10 Thought Leader in Retail and eCommerce, a Top 25 Thought Leader inCareers, a Top 50 Thought Leader in Agentic AI, AGI and Management, and a Top 100 Thought Leader in AI Ethics, Marketing, Digital Transformation and Transformation. Thinkers 360 also awarded him an Elite Expert Certification in Retail, a Master Expert Certification in Management, and named him a Certified Expert in AI, Marketing, and Digital Transformation. Thinkers 360 also named him a Top Digital Voice for 2024, 2025 and 2026. He is an advisory council member at the Retail Cloud Alliance. He was most recently the partner marketing leader for retail & consumer goods in the Americas at Microsoft.

Casey Golden, is the North America Leader for Retail & Consumer Goods at CI&T, and CEO of Luxlock. She is a RETHINK Retail Top Retail Expert from 2023 - 2026, and Retail Cloud Alliance advisory council member. After a career on the fashion and supply chain technology side of the business, Casey is obsessed with the customer relationship between the brand and the consumer and is slaying franken-stacks and building retail tech! 

Episode Music.

Includes music provided by imunobeats.com, featuring Overclocked, and E-Motive from the album Beat Hype, written by Heston Mimms, published by Imuno.