How I AI How Webflow’s CPO built an AI chief of staff to manage her calendar, prep for meetings, and drive AI adoption | Rachel Wolan
100 snips
Dec 29, 2025 
Rachel Wolan, Chief Product Officer at Webflow, is a hands-on coder who developed a custom AI chief-of-staff application. She shares her journey of how this innovative tool helps her manage her calendar and prep for meetings efficiently. Rachel discusses the importance of executives embracing AI by building personal applications to drive authentic organizational change. She also highlights the outcomes of company-wide 'builder days' that significantly increased AI tool adoption, emphasizing the need for leaders to be actively involved in learning AI technologies.
AI Snips
Chapters
Transcript
Episode notes
Return To Hands-On Building
- Rachel returned to hands-on coding after vibe coding rekindled her developer roots and she built a weekend app for her kids.
- That experience led her to run dozens of small AI-native prototypes and make Cloud Code her daily driver.
Learn AI By Building A Personal Project
- Start with a personal, small project to learn AI tooling and get hooked quickly.
- Use a short weekend build to prove concepts and accelerate skill adoption.
An Iterative Chief-Of-Staff Build
- Rachel iteratively built an AI chief-of-staff over many attempts and currently runs multiple rotating agents for different tasks.
- The product remains a single-user, evolving utility she uses daily and shares to model behavior for her team.