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

43 min episode · 2 min read
·
Rachel Wolan

Episode

43 min

Read time

2 min

Topics

Leadership, Design & UX, Artificial Intelligence

AI-Generated Summary

Key Takeaways

  • 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.

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.

Notable Moment

Wolan's AI chief of staff analyzes her calendar and delivers brutal feedback that she operates like a senior PM rather than a CPO, spending time reviewing PRDs and recording marketing videos instead of strategic work—forcing honest reflection on executive time allocation.

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Episode Transcript

So you've built yourself an AI chief of staff. The AI chief of staff is actually something that I have been trying to build since I started vibe coding. There's a lot of repetitive things that I have to do. For example, like prepping for podcasts and speaking engagements and stuff like that. And so I've built an agent that preps me. Let's go into a specific workflow of how this chief of staff actually helps you with do something. I think you did a little prep for this podcast. I basically prompted it and said, hey, let's generate a How AI flow. And so I was trying to get it to tell me what should I actually actually demo that is gonna be part of this chief of staff app. And then what actually ends up getting output is this. It gives me an executive summary. Here are three different ways you could tell me about yourself and web flow. Just the ability to be prepped even in a few minutes ahead of these things can can really make your life better. Welcome back to How I AI. I'm Claire Vaux, product leader and AI obsessive here on a mission to help you build better with these new tools. Today's episode is all about the AI native executive. We have Rachel Wollan, CPO at Webflow, who's gonna show us how she uses AI, quad code, and personal software to run her life and her business day using AI as an executive. She's also gonna show us her formula for teaching teams how to use AI, drive adoption, and get them in those new tools with excitement. Let's get to it. This episode is brought to you by Graphite, the AI powered code review platform, helping engineering teams ship higher quality software faster. As developers adopt AI tools, code generation is accelerating, but code review hasn't caught up. PRs are getting larger, noisier, and teams are spending more time blocked on review than building. Graphite fixes this. Graphite brings all your code review essentials into one streamlined workflow. Stacked diffs, a cleaner, more intuitive PR page, AI powered reviews, and an automated merge queue, all designed to help you move through review cycles faster. Thousands of developers rely on Graphite to move through review faster so you can focus on building, not waiting. Check it out at graphitedev.link/howiai to get started. That's graphitedev.link/howiai. Rachel, welcome to How I AI. The reason why we are doing this podcast together is we were sitting at a very recent San Francisco based AI event, And we were talking about how so much of the discourse is around the AI native PM, the AI native engineer, basically, like the AI native IC. And we spent a lot of time on that topic here at How I AI. But you and I have been chief product officers, and we wanna talk about the AI native executive. And I think your workflow and the tools that …

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Keep Reading

Books, tools, and gear mentioned in this episode

SignalCast may earn commission on purchases via these links.

Tools

  • WebflowRecommended

    by Webflow

    Run organization-wide prototype days where all teams stop regular work to build with AI tools (Cursor, Figma, Webflow)
  • Claude CodeRecommended

    by Anthropic

    Wolan built a locally-hosted app using Claude Code that connects to Google Calendar and Gmail via API tokens with limited permissions
  • by Google

    connects to Google Calendar and Gmail via API tokens with limited permissions (read-only calendar, draft-only email)
  • by Google

    connects to Google Calendar and Gmail via API tokens with limited permissions (read-only calendar, draft-only email)
  • CursorRecommended
    Run organization-wide prototype days where all teams stop regular work to build with AI tools (Cursor, Figma, Webflow)
  • FigmaRecommended

    by Figma

    Run organization-wide prototype days where all teams stop regular work to build with AI tools (Cursor, Figma, Webflow)
  • SPONSORS [Graphite, url: graphitedev.link/howiai]

company

  • SPONSORS [Atlassian for Startups, url: atlassian.com/startups/howiai]

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