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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...
Rachel Wolan, CPO at Webflow, demonstrates how she built a custom AI chief-of-staff application using vibe coding tools to manage her executive workload. She shares her journey from coding at 16 to returning to hands-on development through AI-assisted tools, building personal software that integrates with her calendar, email, and meetings. The episode covers both her personal AI workflows and her framework for driving AI adoption across her product organization through structured 'builder days' that have achieved 80+ prototypes and sustained tool adoption.
Rachel introduces her custom-built AI chief of staff that helps prep for meetings, manage calendar, and provide executive support. She explains how vibe coding tools like Lovable enabled her to return to coding after 6-7 years, building her first app (a kids' memory app) in a weekend and now maintaining dozens of personal applications.
Rachel demonstrates how her AI chief of staff performs daily calendar triage and email management. The system uses Google Cloud API tokens stored in .env files, with carefully scoped permissions (read-only for calendar, draft/archive/label for Gmail) to maintain appropriate guardrails while automating repetitive executive tasks.
Rachel shows how she uses her AI chief of staff to prepare for podcasts and speaking engagements in just minutes. The system generates executive summaries, talking points, and structured outputs that help her operate as a 'just-in-time executive' who can be well-prepared despite back-to-back schedules.
Rachel demonstrates using her AI chief of staff to prep for networking dinners by uploading screenshots of guest lists. The system performs web and LinkedIn searches on each attendee, provides venue information, suggests conversation starters, and identifies priority connections based on her personal context stored in markdown files.
Rachel explains her architecture choice of using markdown files as the source of truth for her personal software. This approach eliminates database complexity, makes content easily accessible to both web UI and AI agents, and enables cross-tool context sharing through simple file references.
Rachel shares her 'builder days' framework that drove 80+ prototypes and sustained AI tool adoption across her product organization. The structured approach includes warm-up assignments, multiple tool tracks (Cursor, Figma, Webflow), support channels, judging panels with CEO, and prizes to create both top-down mandate and bottom-up enthusiasm.
Rachel uses Hex dashboards to track AI tool adoption across roles before and after builder days. She applies the innovation adoption curve framework, identifying early adopters who build scaffolding for the early majority, with the goal of moving the entire organization toward sustained daily AI usage rather than just spike events.
Rachel discusses how she's reinventing every aspect of team operations for AI fluency, including redoing career ladders to emphasize not just tool fluency but leading, owning, and pushing product limits. She evaluates teams across dimensions like data insights, tool fluency, builder culture, and interviewing practices.
Rachel shares her prompting technique when AI isn't delivering desired results: clear Claude Code context and start fresh, then use quantified multipliers like '10x more' for moderate changes or '100x more' for dramatic shifts. This technique leverages models' affinity for numerical calibration.
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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