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Jake Chen, Strategy Lead at Waymo

Jake Chen

Strategy Lead at Waymo

I study what happens when AI meets the real world.

How it reshapes decisions, organizations, and the systems that run them — and what the best teams do differently. Previously McKinsey, HubSpot, Microsoft. MIT Sloan MBA.

Now

Day job

Leading strategy at Waymo — helping autonomous mobility scale from prototype to product.

Writing about

What happens when AI systems start making real decisions. Second-order effects. The gap between what gets announced and what actually ships.

After hours

Tinkering with code. Built an AI-themed game arcade and coded this site from scratch in TypeScript and React.

Featured project

Resume Runner

Jump over career milestones to build my resume in real time. From undergrad to Waymo — clear all seven blocks to see the full picture. Built with Canvas and React.

Play now

Try it yourself

Interactive experiments

What's your AI strategy score?

Question 1 of 5

Your AI model makes a mistake that costs a customer money. What happens next?

The bottleneck finder

Pick your industry. I'll tell you what AI makes abundant — and where the new bottleneck forms.

Recent essays

All writing

On the shelf

Books that shaped how I think

Thinking in Systems

Donella Meadows

The best book on understanding why complex organizations behave the way they do. I re-read it every year.

The Alignment Problem

Brian Christian

The most honest book about what goes wrong when AI systems meet the real world. Required reading for anyone deploying AI.

Competing in the Age of AI

Iansiti & Lakhani

Gets the operating model question right — AI changes how firms run, not just what they sell.

Thinking, Fast and Slow

Daniel Kahneman

Every decision framework I use has roots here. The gap between System 1 and System 2 is the gap between a demo and a product.

Join the conversation

I send essays when they're ready — honest thinking on how AI is reshaping decisions, industries, and the systems we rely on. No spam, no schedule.