Pain points identified
What's broken
- Cross-product context fragments as the portfolio crosses ~5 products
- Architectural decisions get re-litigated every quarter — the rationale isn't durable
- Lessons from painful 3am incidents don't transfer to the next product
- Marketing, /help pages, and changelogs drift the moment code ships
- Every Claude Code session starts cold — no memory of the prior session
- Notion / Obsidian are passive: they wait to be queried, never act or coordinate