(2025-12-29) Vo How Webflow's CPO Built An AI Chief Of Staff

Claire Vo: How I AI: How Webflow's CPO built an AI chief of staff. How Webflow’s CPO built an AI chief of staff to manage her calendar, prep for meetings, and drive AI adoption.

Every Monday, host shares a 30- to 45-minute episode with a new guest demoing

Rachel Wolan, CPO at Webflow, walks through how she built her own AI chief of staff to run her week—prepping for meetings, auditing her calendar, triaging email, and giving her brutally honest feedback. Claire and Rachel dig into why building personal AI software is the fastest way for executives to really understand what’s possible with AI, how “builder days” can drive org-wide adoption, and why treating software as disposable is a superpower.

Biggest takeaways:

The most important outcome is seeing what’s possible. The most heartwarming feedback from Builder Day participants was that it was “eye-opening”—people didn’t understand what was possible until they tried it themselves. Rachel calls this “getting blue-pilled,” when people suddenly step into a new part of their professional journey.

Personal software can be ephemeral and imperfect. Rachel builds for an “N of 1” (herself), which allows for hyper-customization. (situated software)

Markdown files are the perfect knowledge base for personal AI. She keeps manual PKM notes in markdown, too, now, so they can be fed into AI.

Effective AI adoption requires both top-down mandates and bottom-up enthusiasm. Rachel tells her team, “You can’t get into a meeting with me without a prototype,” (vibe prototyping)

Calendar delegation is a key executive use case. The AI analyzes Rachel’s calendar and suggests which meetings she can skip, delegate, or make asynchronous, even drafting the delegation messages she can send. This reduces the friction of managing time and helps her focus on high-impact work.

Listen https://www.youtube.com/watch?v=BTcG59ZR9sg]

• I think it's ClaudeCode
• personal/local webapp - plays with design: "theme like Apple Notes"
  • lots of calendar-driven dialog (because that's how her day is managed)
• interacts with GoogleCalendar
  • actually app gives her custom design/view of the calendar, which lets her control what shows up in-line
  • "which meetings tomorrow can I delegate, or change to async?"
  • working on drafting slack-message
• "the only thing in your calendar tomorrow that will matter in 6mo is X" -
• daily index card - 3 MITs; end-day accomplishments (she enters these herself? no AI help there?)
• but primary interface is still chat/terminal
• 21:20: Claire makes cool point about impossibility of constant triage of massive amounts of disconnected bits (see TeamGarden)
• benefits
  • gets her hands dirty in AI, relevant to product changes
  • gets her closer to their existing codebase
• Claire: is this a product, or does each person have to build themselves?
  • anthropic could probably provide a base-case
  • probably network of people sharing bits
• evaluating team/practice - rubric specifically applying AI to each existing aspect of PM job
• giving feedback to model: "be 2x meaner" (use numbers)