#176 - Dean Phillips: The Cold Email That Became a Head of Product Strategy Job

About Dean Phillips

Dean Phillips is the Head of Product Strategy at ClickUp, where he leads the product direction for ClickUp Docs and the company’s emerging AI-powered Super Agents. Rising to prominence in the early 2020s, he became known for translating complex workflows into opinionated, high-leverage product systems inside a platform used by millions of users worldwide. At ClickUp, he currently oversees strategic initiatives that connect document creation, task management, and AI automation into a single unified experience.

Previously, as Head of Product Strategy and Product Manager at ClickUp, he helped scale the product organization through more than five years of rapid growth, serving in core product roles from December 2020 through at least early 2026. He became known for shipping multi-quarter initiatives that spanned Docs, collaboration surfaces, and workflow automation, partnering closely with engineering and data teams to improve productivity at scale. Before ClickUp, he served as Chief Technology Officer at The Pattern Trader, where over four and a half years he led full-stack product and technology efforts for a trading and analytics platform.

Hey, Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.

So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.

I make this for myself first. If you read the way I do, you’ll want it too.

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