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

2025-05-13 · Source: Lenny's Newsletter · Field: Technology & Digital — Artificial Intelligence & Machine Learning, Software Development & Engineering, Project & Product Management · Depth: Intermediate, extended

Summary

Rachel Woolen, CPO at Webflow, demonstrates her "AI Chief of Staff," a personalized agent-based system built using vibe coding to manage executive tasks. This system, developed over a year, automates podcast prep, morning calendar triage, email management, and even dinner networking research. It integrates with Google Calendar and Gmail via API tokens, with carefully configured guardrails for read-only calendar access and draft-only email creation. Woolen also details Webflow's "Builder Days," an initiative to drive AI adoption across product, design, data science, and engineering teams. These events involve organization-wide prototyping with tools like Cursor, Figma Make, and Webflow, supported by engineers, judging panels, and prizes, resulting in over 80 prototypes and significant increases in AI tool usage and team confidence.

Key takeaway

For CPOs and executives aiming to enhance personal productivity and scale AI adoption across their teams, building custom AI agents can significantly streamline daily operations like meeting prep and calendar management. Your organization should consider implementing structured "Builder Days" or hackathons, providing tools, education, and incentives to foster hands-on AI experience and drive sustained engagement, ensuring teams are not just aware of AI but actively building with it.

Key insights

Executives can build personalized AI agents to automate routine tasks and drive organizational AI fluency through structured "Builder Days."

Principles

• Hands-on AI building fosters deep product understanding.
• Personalized software can be highly effective for individual productivity.
• Organizational AI adoption requires both top-down mandate and bottom-up engagement.

Method

Develop AI agents for specific executive workflows (e.g., calendar, email, prep) using API tokens and markdown for context. Implement "Builder Days" with tools, support, and incentives to scale AI proficiency across teams.

In practice

• Use markdown files for agent context and personal app content.
• Start AI skill development with personal, weekend projects.
• Quantify prompt instructions (e.g., "10x more harsh") for better model calibration.

Topics

• AI Chief of Staff
• AI Agent Development
• Organizational AI Adoption
• Prompt Engineering
• Personal AI Tools

Best for: VP of Engineering/Data, Executive, Product Manager, CTO, Director of AI/ML, AI Product Manager

Related on AIssential

• How Webflow’s CPO built an AI chief of staff to manage her calendar and drive internal AI adoption — Executives can build personalized AI agents to automate tasks and drive organizational AI fluency through hands-on "builder days."
• How Webflow’s CPO built an AI chief of staff to manage her calendar, prep for meetings, and drive AI adoption | Rachel Wolan — Executives can build personalized AI tools to enhance productivity and drive organizational AI adoption.
• The 4 AI Team Members Execs Should Hire Right Now — Executive AI usage, guided by specific principles, significantly predicts broader organizational AI adoption and effectiveness.
• Work in the Age of Infinite Agents — AI agents will fundamentally reshape knowledge work by enabling unprecedented scale and democratizing complex tasks.
• The Builder-PM Manifesto — Product management is fundamentally changing as AI's "harness" operating layer shifts scaling laws from models to team-level strategic framing.
• Transcript: ‘We Gave Every Employee an AI Agent. Here's What Happened.’ — Personalized AI agents, reflecting user personalities, enhance organizational collaboration and individual productivity.

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