How Webflow’s CPO built an AI chief of staff to manage her calendar, prep for meetings, and drive AI adoption | Rachel Wolan
December 29, 2025
AI Summary
5 min read🎙️ The Voices & The Context
- The Format: This interview between host Claire Vauxh and guest Rachel Wolin dives into hands-on AI tools for executives, blending live demos with energetic storytelling to showcase practical AI integration in high-level product leadership. Technical yet inspirational, it pulses with shared excitement over "vibe coding" breakthroughs.
- The Format: An interview with live app demos and conversational rapport.
- The Key Players:
- Guest: Rachel Wolin, CPO at Webflow, renowned for her vibe-coding revival after years away from hands-on building; she's famous for prototyping AI-native products like Webflow's new app-gen tool and her personal AI chief of staff app, making her a trailblazing "AI Native Executive."
- Host: Claire Vauxh, AI-obsessed product leader, mirrors Rachel's journey with infectious enthusiasm, fostering a seamless, geeky chemistry around exec hacks and team adoption.
🗝️ Key Themes & Topics
The episode explores AI as a personal and organizational superpower for executives, emphasizing hands-on building over theory, with demos revealing how AI tames chaos in calendars, emails, and prep while sparking team-wide adoption.
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What you'll learn
- 1 CPO at Webflow; shares AI workflows, vibe coding, and personal software for executives
- 2 Episode focus: AI Native Executive, team AI adoption strategies
- 3 Started coding at 16; returned after 6-7 year hiatus with AI tools like Claude
- 4 First project: Weekend-built kids' memory app on localhost; now daily driver for dozens of apps
- 5 Parallels host's story: Hands-on building reignites coding passion for busy execs
- 6 Advice: Start personal projects to get hooked on AI tools
- 7 First vibe-coded app; iterated for repetitive tasks like podcast/speaking prep
+ Full timestamped outline available in the app
Show Notes
Rachel Wolan, the chief product officer at Webflow, has embraced AI not just as a product leader but as a hands-on builder. A coder since age 16, Rachel has returned to her technical roots by creating a custom AI chief-of-staff application that helps manage her executive workload. In this episode, she demonstrates how she uses personal AI software to prep for meetings, triage her calendar, manage emails, and even get brutally honest feedback about how she’s spending her time.
What you’ll learn:
- How Rachel built a custom AI chief-of-staff application that integrates with her calendar, email, and more
- Why building personal software can be a gateway to understanding AI’s capabilities for executives
- How her AI agents help her prep for podcasts, dinners, and meetings with just-in-time information
- The technical approach to building personal AI software using markdown files, API tokens, and multiple LLM interfaces
- How Rachel organized company-wide “builder days” that dramatically increased AI tool adoption across her organization
- Why she believes executives must lead by example in AI adoption to authentically drive organizational change
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Brought to you by:
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Atlassian for Startups —From MVP to IPO
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In this episode, we cover:
(00:00) Introduction to Rachel Wolan
(02:26) Why Rachel started leaning into AI
(06:26) Building an AI chief of staff
(08:17) Prepping for the podcast
(10:00) Rachel’s morning flow with her AI chief of staff
(14:14) Designing a personalized interface with custom note cards
(16:34) Getting “brutal truth” feedback from your AI assistant
(19:34) Email triage and management workflows
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