🎙️This week on How I AI: How Webflow’s CPO built an AI chief of staff

Your weekly listens from How I AI, part of the Lenny’s Podcast Network

Every Monday, host Claire Vo shares a 30- to 45-minute episode with a new guest demoing a practical, impactful way they’ve learned to use AI in their work or life. No pontificating—just specific and actionable advice.

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

Brought to you by:

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• Atlassian for Startups—From MVP to IPO

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:

1. 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.

2. Personal software can be ephemeral and imperfect. Rachel builds for an “N of 1” (herself), which allows for hyper-customization. She creates widgets for specific needs (like Q4 roadmap planning) that can be tossed away when no longer needed. This approach treats software as being as accessible as documents: build it, use it, discard it when done.

3. Markdown files are the perfect knowledge base for personal AI. Rachel stores everything from dinner research to product documentation in markdown files, making them easily accessible to both her web app and any LLM she uses. This creates a personal knowledge graph that improves all her AI interactions.

4. 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,” creating clear expectations. But she also nurtures grassroots enthusiasm through Builder Days, prizes, and recognition.

5. 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 now on YouTube | Spotify | Apple Podcasts

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Catch you next week,
Lenny

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