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
2025/12/29
How Webflow’s CPO built an AI chief of staff to manage her calendar, prep for meetings, and drive AI adoption | Rachel Wolan
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
2025/12/29
Rachel Wolan, Webflow's chief product officer, shares her journey of re-engaging with coding through AI, transforming how she manages executive responsibilities. Rather than relying solely on off-the-shelf tools, she built a custom AI chief of staff to handle complex, personal workflows—offering a glimpse into the future of personalized productivity for leaders.
Leveraging tools like Claude and Cursor, Rachel created an AI-powered system that integrates with her calendar, email, and APIs to automate meeting prep, triage messages, and generate contextual briefs for events like podcasts and networking dinners. The AI provides candid performance feedback, revealing gaps in her leadership focus and helping her operate at a strategic level. By using markdown files and modular interfaces, she designed a flexible, personal operating system that evolves with her needs. To scale this mindset across Webflow, she launched 'builder days,' immersive events that empower employees to create AI-driven prototypes, fostering widespread adoption. These initiatives combine top-down leadership with grassroots innovation, emphasizing that executives must model AI fluency to drive authentic organizational change. Her approach highlights how hands-on experimentation with AI can deepen technical understanding and unlock new levels of efficiency.
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Rachel Wolan built an AI chief of staff to handle her podcast prep and speaking engagements.
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Built a kids' memory app in a weekend using Claude Code.
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The AI chief of staff is designed to help Rachel level up her team through personalized, AI-driven workflows.
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The AI pointed out not blocking energy, not taking care of oneself, and not spending enough time with customers.
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The app mimics blue-lined note cards for a tactile, personal feel
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The AI chief of staff gives brutal truth feedback, revealing the speaker acts more like a senior PM than a CPO.
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Atlassian for Startups offers up to 50 free seats on premium editions of Jira and Confluence.
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AI chief of staff creates full prep docs using guest lists and personal context
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Using Codex helps her understand the app's codebase.
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Over 80 prototypes were built in a single Builder Day across multiple functions.
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CPOs and executives should get hands-on with coding as a crucial hard skill
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Use quantifiable prompts like '10x' to improve AI output when results are lacking