Episode Summary

When Katelyn Lesse was leading engineering at Stripe, she noticed everything around her shifting because of AI. So she left, and joined Anthropic. Today she leads platform engineering at one of the most important AI companies in the world, which is why we were so thrilled to host her for Anthropic's first ever interview in Sydney.

Katelyn does not lead with technical jargon. She leads with a question every builder needs to sit with right now. Are you building on the exponential, or are you stuck on the linear? Most people, she says, are already further behind than they realise.

In this episode she shares the exact framework she uses to think about building in the AI era, why your frustrations with Claude are actually signals you are onto something, and what it really means to be AGI pilled inside Anthropic.

Time Stamps

00:00 Intro

02:53 AI Hack: Using Claude to Pick Wine

03:42 Katelyn's Background and Path to Anthropic

05:32 Why She Left Stripe to Join Anthropic

11:22 What Building on the Exponential Means

11:48 Why Australia Is a Top AI Market

13:05 Is the Claude Obsession Healthy?

15:20 The Framework for Building AI Products

16:38 Why Evals Are Non-Negotiable

18:18 Inside Anthropic's Developer Platform

20:11 What Is Harness Engineering?

25:13 AI Security, Sandboxes and Human in the Loop

29:09 Cloud Managed Agents Explained

31:56 Open Source MCP vs Closed Claude

33:48 How AI Is Changing Engineering Teams

36:24 How to Choose the Right AI Coding Tool

39:12 The End of the Traditional Tech Team

44:30 The AI Magic Moment Everyone Remembers

45:30 What It Means to Be AGI Pilled

47:21 Rapid Fire With Anthropic

49:56 Advice for Developers Building With AI

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