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

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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 I AI

How I AI

2025/12/29
OverviewShownoteHighlightsTranscriptChaptersPins

Shownote

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 manag...

Highlights

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.
01:30
Rachel Wolan built an AI chief of staff to handle her podcast prep and speaking engagements.
02:26
Built a kids' memory app in a weekend using Claude Code.
06:26
The AI chief of staff is designed to help Rachel level up her team through personalized, AI-driven workflows.
10:00
The AI pointed out not blocking energy, not taking care of oneself, and not spending enough time with customers.
14:17
The app mimics blue-lined note cards for a tactile, personal feel
16:35
The AI chief of staff gives brutal truth feedback, revealing the speaker acts more like a senior PM than a CPO.
22:35
Atlassian for Startups offers up to 50 free seats on premium editions of Jira and Confluence.
23:31
AI chief of staff creates full prep docs using guest lists and personal context
28:18
Using Codex helps her understand the app's codebase.
32:51
Over 80 prototypes were built in a single Builder Day across multiple functions.
35:39
CPOs and executives should get hands-on with coding as a crucial hard skill
40:57
Use quantifiable prompts like '10x' to improve AI output when results are lacking

Chapters

Introduction to Rachel Wolan
00:00
Why Rachel started leaning into AI
02:26
Building an AI chief of staff
06:26
Prepping for the podcast
08:17
Rachel’s morning flow with her AI chief of staff
10:00
Designing a personalized interface with custom note cards
14:14
Getting “brutal truth” feedback from your AI assistant
16:34
Email triage and management workflows
19:34
Prepping for networking dinners and events
23:31
The result of building an AI chief of staff
28:18
Organizing “builder days” to drive AI adoption
30:09
Measuring the impact of AI adoption initiatives
35:38
Lightning round and final thoughts
38:00

Transcript

Claire Vo: So you've built yourself an AI chief of staff. Rachel Wolan: The AI chief of staff is actually something that I have been trying to build since I started write coding. There's a lot of repetitive things that I have to do, for example, like prep...