Jackie Pines gave Claude a memory for her whole career

Jacqueline Pines · Published November 4, 2026

Jackie Pines showed us her Career Brain File and a scheduled task she calls Brain-sync, both built with Claude projects and skills. Eight minutes was nowhere near enough. We wanted the whole tour.

Most of us start every AI chat by explaining ourselves. Who we are, what we've worked on, what we're good at. Again. And again.

Jackie fixed that for herself. She did it the way you'd expect from someone who worked as a product and customer success manager on a knowledge management tool. At Built by Willa, our member show and tell in October, she walked us through her Career Brain File and the system that keeps it running.

Think like an information architect

Information architecture is the practice of organizing information so it's easy to find, use and understand. Jackie brought that knowledge management mindset into Claude and built her Career Brain around three goals:

1. One source of truth about her career: the Career Brain File
2. A process to keep the source up to date, so she doesn't have to update more than once: Brain-sync
3. A record of every change and why it was made: Changelog

The part everyone wanted more of

It starts with a Claude project with clear instructions. A discovery skill builds the Career Brain File through coaching conversations, and Brain-sync copies new changes from Changelog back in so it never falls out of date. But what really landed was how Jackie structures the Claude project itself. It's a system, not a pile of notes, and that's why it works.

What's next

Jackie is now working on GenAI fundamentals training, AI policy for individuals, consultants and small business owners, plus a framework for keeping ownership of your work when you partner with AI. If her brain file is any sign, it's going to be beautifully organized.

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