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How I AIHow Webflow’s CPO built an AI chief of staff to manage her calendar and drive internal AI adoption
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At a glance
WHAT IT’S REALLY ABOUT
Webflow CPO builds an AI chief of staff for executive leverage
- Rachel Wolan explains how recent “vibe coding” tools pulled her back into hands-on building, leading her to create a personal AI chief of staff app that supports just-in-time executive work.
- She demos concrete workflows: calendar analysis and delegation suggestions, “brutal truth” executive coaching, Gmail triage with guarded permissions, and dinner/event networking prep from a screenshot guest list.
- A key design pattern is storing personal and company context as Markdown inside a repo, making it easy to render in a simple UI and reusable by agents.
- Wolan then shifts to organizational adoption, describing Webflow’s builder days—tool access, structured tracks, on-call helpers, prizes, and measurement—to move teams from curiosity to sustained AI tool usage.
IDEAS WORTH REMEMBERING
5 ideasBuild personal software for executive bottlenecks first.
Wolan targets repetitive, high-friction executive tasks (meeting prep, calendar triage, email overload) where even small time savings and better context dramatically improve daily effectiveness.
Use tight permissions as the default guardrail for agents.
Her calendar integration is read-only, while Gmail is constrained to specific actions (draft, read, archive, label). She explicitly “takes power away” when an agent feels over-authorized.
“Brutal truth” prompting turns an assistant into lightweight executive coaching.
By instructing the agent to be harsh, she gets direct feedback (e.g., behaving like a senior PM vs. CPO) that highlights misallocation of time and pushes higher-leverage behavior.
Separate contexts (multiple Claude sessions) to improve answer quality.
She runs different terminals for different task types to avoid bloated context and to keep similar questions grouped, which she finds yields more consistent outputs.
Markdown files are a powerful, low-complexity knowledge base.
She stores “about me,” communication preferences, and product release summaries as Markdown in-repo, enabling easy UI rendering and making the same content reusable across agents without a database.
WORDS WORTH SAVING
5 quotesYou're a CPO with, like, no regular visible customer contact. Fatal flaw.
— Rachel Wolan (AI chief of staff output, read by Rachel)
The brutal truth is... you're operating as a senior PM, not a CPO.
— Rachel Wolan (AI chief of staff output, read by Rachel)
The number one skill you need to learn as an executive is improv.
— Claire Vo
It would be inauthentic for me to tell them, 'Hey, you need to prototype with AI,' if this isn't something that I'm doing every single day.
— Rachel Wolan
I call it getting blue-pilled.
— Rachel Wolan
High quality AI-generated summary created from speaker-labeled transcript.
