Why Enterprise AI Fails | Home Depot | Klarna | Walmart with Ben Pickett Ep50 episode artwork

EPISODE · Aug 24, 2026 · 44 MIN

Why Enterprise AI Fails | Home Depot | Klarna | Walmart with Ben Pickett Ep50

from AI Outcomes · host Ben Drakes

Klarna replaced around 700 support people with one AI agent, then started hiring humans back. Walmart had the same technology and redrew the work instead. Home Depot had AI in 600 stores six weeks after ChatGPT launched, and it wasn't a chatbot.Ben Pickett joins Ben Drakes for the first of a new fortnightly strand on what's actually happening inside enterprise AI rollouts — the ones that went wrong, and the ones that quietly went right.Five stories, and one thread running through all of them: the difference between the company that got hurt and the company that didn't was never the technology and rarely the budget. It was whether one person had been named to own the work.00:00 Live Test and Episode 5001:35 Agenda and Guest Intro06:02 Home Depot AI at Scale10:10 Adoption Lessons and Human Loop13:16 Anthropic Security Breakout20:29 Klarna vs Walmart AI Strategy27:41 Shadow AI in the Workplace34:44 Amazon and AI Deployment Risks42:36 Wrap Up and SubscribeBen Pickett writes Enterprise Field Notes and is Co-Founder and COO at Swa.Free worksheets, no signup: benpickett.com/aioBen Pickett: https://www.linkedin.com/in/benpickett/Ben Drakes: https://www.linkedin.com/in/ben-drakes/Website: https://bendrakes.com

Episode metadata supplied by the publisher feed · Published Aug 24, 2026

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Klarna replaced around 700 support people with one AI agent, then started hiring humans back. Walmart had the same technology and redrew the work instead. Home Depot had AI in 600 stores six weeks after ChatGPT launched, and it wasn't a chatbot. Ben Pickett joins Ben Drakes for the first of a new fortnightly strand on what's actually happening inside enterprise AI rollouts — the ones that went wrong, and the ones that quietly went right. Five stories, and one thread running through all of t...

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Why Enterprise AI Fails | Home Depot | Klarna | Walmart with Ben Pickett Ep50

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