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How Webflow’s CPO built an AI chief of staff to manage her calendar and drive internal AI adoption

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 manage her executive workload. In this episode, she demonstrates how she uses personal AI software to prep for meetings, triage her calendar, manage emails, and even get brutally honest feedback about how she’s spending her time. *What you’ll learn:* 1. How Rachel built a custom AI chief-of-staff application that integrates with her calendar, email, and more 2. Why building personal software can be a gateway to understanding AI’s capabilities for executives 3. How her AI agents help her prep for podcasts, dinners, and meetings with just-in-time information 4. The technical approach to building personal AI software using markdown files, API tokens, and multiple LLM interfaces 5. How Rachel organized company-wide “builder days” that dramatically increased AI tool adoption across her organization 6. Why she believes executives must lead by example in AI adoption to authentically drive organizational change *Brought to you by:* Graphite—Your AI code review platform: https://graphitedev.link/howiai Atlassian for Startups—From MVP to IPO: https://atlassian.com/startups/howiai *In this episode, we cover:* (00:00) Introduction to Rachel Wolan (02:26) Why Rachel started leaning into AI (06:26) Building an AI chief of staff (08:17) Prepping for the podcast (10:00) Rachel’s morning flow with her AI chief of staff (14:14) Designing a personalized interface with custom note cards (16:34) Getting “brutal truth” feedback from your AI assistant (19:34) Email triage and management workflows (23:31) Prepping for networking dinners and events (28:18) The result of building an AI chief of staff (30:09) Organizing “builder days” to drive AI adoption (35:38) Measuring the impact of AI adoption initiatives (38:00) Lightning round and final thoughts *Tools referenced:* • Claude: https://claude.ai/ • Claude Code: https://claude.ai/code • Cursor: https://cursor.com/ • Google Calendar API: https://developers.google.com/calendar • Gmail API: https://developers.google.com/gmail • Webflow: https://webflow.com/ • Figma: https://www.figma.com/ • Make: https://www.make.com/ • Hex: https://hex.tech/ *Other references:* • The complete beginner’s guide to coding with AI: from PRD to generating your very first lines of code: https://www.lennysnewsletter.com/p/the-complete-beginners-guide-to-coding *Where to find Rachel Wolan:* LinkedIn: https://www.linkedin.com/in/rachelwolan/ X: https://x.com/rachelwolan Webflow: https://webflow.com *Where to find Claire Vo:* ChatPRD: https://www.chatprd.ai/ Website: https://clairevo.com/ LinkedIn: https://www.linkedin.com/in/clairevo/ X: https://x.com/clairevo _Production and marketing by https://penname.co/._ _For inquiries about sponsoring the podcast, email jordan@penname.co._

Claire VohostRachel Wolanguest
Dec 29, 202543mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Webflow CPO builds an AI chief of staff for executive leverage

  1. 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.
  2. 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.
  3. 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.
  4. 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 ideas

Build 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 quotes

You'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

Vibe coding as an executive skill multiplierAI chief of staff for an “N of one”Calendar read-only + delegation recommendationsGuardrails/permissions for agent actions (Gmail drafts, archiving, labeling)Markdown-as-database for personal/context docsEvent networking prep from screenshots + web/LinkedIn lookupBuilder days to drive sustained AI adoption (tracks, support, prizes, metrics)

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