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
How I AI
•December 29, 2025•43 min
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How I AI•Dec 29, 2025
Key Takeaways
- •Built AI chief of staff with Claude agents, Google APIs
- •Automates daily calendar triage, meeting prep, and delegation suggestions
- •Generates email drafts, archives, and priority alerts via AI
- •Uses rapid vibe coding to create personal, disposable widgets
- •Shows AI native executive model driving team adoption and productivity
Pulse Analysis
In this episode, Webflow CPO Rachel Wollin reveals how she transformed a personal productivity challenge into an AI‑powered chief of staff. Leveraging Claude‑based agents and secure Google Calendar and Gmail tokens, she built a bespoke assistant that prepares executive summaries, suggests meeting agendas, and even drafts responses. The conversation highlights why senior product leaders are turning to AI native tools: they eliminate repetitive prep, free mental bandwidth, and enable real‑time improvisation—critical skills for executives constantly shifting between strategic and tactical contexts.
Wollin walks listeners through the technical stack behind her system. A set of environment variables stores API credentials, while multiple terminal‑based Claude instances keep context lightweight. The assistant scans her calendar each morning, flags over‑booked slots, recommends delegations, and surfaces customer‑interaction gaps that a traditional chief of staff would catch. A parallel email agent archives low‑value threads, drafts replies for partnership inquiries, and surfaces high‑priority messages. The UI blends a blue‑lined note‑card aesthetic with quick‑flip summaries, proving that even personal tools can benefit from thoughtful design and rapid prototyping.
Beyond the demo, the discussion frames the "AI native executive" as a new leadership archetype. By building N‑of‑1 applications through vibe‑coding platforms, executives can experiment, iterate, and showcase tangible AI value to their teams. This hands‑on approach accelerates adoption, fuels excitement, and demonstrates how AI can augment decision‑making without replacing human judgment. For product leaders seeking scalable productivity gains, Wollin’s workflow offers a replicable blueprint: start with a personal pain point, prototype with low‑code AI agents, and expand the solution to drive organization‑wide transformation.
Episode Description
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:
Graphite—The next generation of code review
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
(23:31) Prepping for networking dinners and events
(28:18) The result of building an AI chief of staff
(30:09) Organizing “builder days” to drive AI adoption
(35:38) Measuring the impact of AI adoption initiatives
(38:00) Lightning round and final thoughts
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Tools referenced:
• Claude: https://claude.ai/
• Claude Code: https://claude.ai/code
• Cursor: https://cursor.com/
• Google Calendar API: https://developers.google.com/calendar
• Gmail API: https://developers.google.com/gmail
• Webflow: https://webflow.com/
• Figma: https://www.figma.com/
• Make: https://www.make.com/
• Hex: https://hex.tech/
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Where to find Rachel Wolan:
LinkedIn: https://www.linkedin.com/in/rachelwolan/
X: https://x.com/rachelwolan
Webflow: https://webflow.com
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Where to find Claire Vo:
ChatPRD: https://www.chatprd.ai/
Website: https://clairevo.com/
LinkedIn: https://www.linkedin.com/in/clairevo/
X: https://x.com/clairevo
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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email jordan@penname.co.
Show Notes
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