This Week on How I AI: How Webflow’s CPO Built an AI Chief of Staff

Summary

In this episode, Webflow CPO Rachel Wolan explains how she built a personal AI "chief of staff" to automate calendar management, meeting prep, email triage, and provide candid feedback. She highlights that creating bespoke, disposable AI tools for oneself reveals what's possible and drives broader adoption through "Builder Days" and a mix of top‑down expectations and grassroots enthusiasm. Key takeaways include the power of markdown‑based knowledge bases, the importance of treating software as an interchangeable document, and using AI to delegate and streamline executive time.