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

December 29, 2025·43 min·6-min readinterviewtechnology
Podzilla Summary (6 min)
TLDR
Rachel Wollin, CPO at Webflow, has built a personalized AI chief of staff using AI-assisted coding tools like Cursor and Claude to automate executive workflows such as calendar triage, email management, meeting prep, and social event research. By building for herself first, she’s not only

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Guest

R

Rachel Wollin

interview on How I AI

Mentions

Books, people, and resources mentioned in this episode.

People

Rachel WollinClaire Vo

Companies

Webflow

Products & Tools

CursorClaudeAppGen

Topics

Artificial IntelligenceProduct ManagementSoftware Engineering

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