How Webflow’s CPO built an AI chief of staff to manage her calendar, prep for meetings, and drive AI adoption | Rachel Wolan

What It Covers

Webflow CPO Rachel Wolan demonstrates her custom-built AI chief of staff that manages her calendar, preps meetings, triages email, and explains her framework for driving AI adoption through builder days across product teams.

Key Questions Answered

• •Personal AI Chief of Staff: Wolan built a locally-hosted app using Claude Code that connects to Google Calendar and Gmail via API tokens with limited permissions (read-only calendar, draft-only email) to analyze her schedule, suggest delegations, and flag overcommitment patterns weekly.
• •Markdown-Powered Personal Apps: Store context as markdown files in your repo instead of databases—personal notes, meeting prep, product updates—so any AI agent can reference them across tools while displaying nicely on front-end interfaces without infrastructure complexity.
• •Builder Day Framework: Run organization-wide prototype days where all teams stop regular work to build with AI tools (Cursor, Figma, Webflow). Provide warm-up assignments, on-call engineer support, judging panels with executives, prizes, and measure sustained adoption post-event to drive 80-plus prototypes.
• •Quantified Prompting Technique: When AI outputs miss the mark, clear context and restart with numerical modifiers—"be 10x more detailed" for incremental changes or "100x more harsh" for complete rewrites—because language models calibrate better to specific numerical targets than vague requests.