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

2025-12-22 · Source: Lenny's Newsletter · Field: Technology & Digital — Artificial Intelligence & Machine Learning, Software Development & Engineering, Data Science & Analytics · Depth: Intermediate, extended

Summary

Rachel Wollin, CPO at Webflow, demonstrates her custom AI Chief of Staff application, built using Claude code, to manage her executive tasks. The app assists with meeting preparation by generating executive summaries and talking points, performs morning triage by analyzing calendar events to identify delegation opportunities and time management issues, and streamlines email management by archiving unnecessary messages and drafting responses. Wollin also uses it for dinner prep, analyzing guest lists from screenshots and providing background on attendees and discussion topics. She emphasizes the importance of hands-on building for executives, noting her return to coding after a six-year hiatus, and highlights the use of Markdown files for context and guardrails for API access to Google Calendar and Gmail. The app, designed for an "N of one," reflects a trend towards personalized, ephemeral software.

Key takeaway

For AI Product Managers or Directors of AI/ML seeking to integrate AI into executive workflows, consider building custom, "N of one" AI applications. Your direct engagement with tools like Claude code and Markdown-based context will not only streamline your own operations but also provide invaluable insights for driving broader organizational AI adoption through initiatives like "builder days," fostering a culture of hands-on experimentation and practical application.

Key insights

Executives can build personalized AI tools to enhance productivity and drive organizational AI adoption.

Principles

• Hands-on building fosters deep understanding of AI capabilities.
• Personalized software can be highly effective for individual workflows.
• AI adoption requires both top-down mandates and bottom-up engagement.

Method

Build AI agents using tools like Claude code, integrating with APIs (e.g., Google Calendar, Gmail) with strict guardrails. Store context in Markdown files for easy model access and display via web UI.

In practice

• Develop a personal AI chief of staff for meeting prep and calendar analysis.
• Use Markdown files as a content source for AI agents.
• Organize "builder days" to accelerate team AI fluency.

Topics

• AI Agents
• Executive Productivity
• AI Adoption Strategies
• AI-assisted Development
• Personalized AI Software

Best for: Director of AI/ML, AI Product Manager, Software Engineer

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Editorial summary, takeaway, and curation by AIssential. Original article published by Lenny's Newsletter.