Rachel Woland, CPO at Webflow, walks through how she built her own AI chief of staff to run her week—prepping for meetings, auditing her calendar, triaging email, and giving her brutally honest feedback. Claire and Rachel dig into why building personal AI software is the fastest way for executives to really understand what’s possible with AI, how “builder days” can drive org-wide adoption, and why treating software as disposable is a superpower.
According to Rachel Woland, here are some few points to consider when building her AI :
1) The most important outcome is seeing what’s possible.
The most heartwarming feedback from Builder Day participants was that it was “eye-opening”—people didn’t understand what was possible until they tried it themselves. Rachel calls this “getting blue-pilled,” when people suddenly step into a new part of their professional journey.
2) Personal software can be ephemeral and imperfect.
Rachel builds for an “N of 1” (herself), which allows for hyper-customization. She creates widgets for specific needs (like Q4 roadmap planning) that can be tossed away when no longer needed. This approach treats software as being as accessible as documents : build it, use it, discard it when done.
3) Markdown files are the perfect knowledge base for personal AI.
Rachel stores everything from dinner research to product documentation in markdown files, making them easily accessible to both her web app and any LLM she uses. This creates a personal knowledge graph that improves all her AI interactions.
4) Effective AI adoption requires both top-down mandates and bottom-up enthusiasm.
Rachel tells her team, “You can’t get into a meeting with me without a prototype,” creating clear expectations. But she also nurtures grassroots enthusiasm through Builder Days, prizes, and recognition.
5) Calendar delegation is a key executive use case.
The AI analyzes Rachel’s calendar and suggests which meetings she can skip, delegate, or make asynchronous, even drafting the delegation messages she can send. This reduces the friction of managing time and helps her focus on high-impact work.
Brian Greenbaum is a product designer at Pendo who accidentally became the company’s AI champion, starting with a single Slack message he sent while on paternity leave. What followed : hands-on workshops, simple demos that changed leadership’s minds, a clear “golden path” for tools and policies, and real adoption across PMs, designers, and engineers. In this sharing, Brian breaks down a practical, repeatable playbook for getting your team excited about AI—and actually using it.
According to Brian Greenbaum, here are some few points to get his team excited about AI :
A) Becoming your company’s AI champion is a career accelerator.
Brian notes, “This initiative has opened so many doors internally. . . I’m having influence way beyond my scope.” As a senior IC designer, he’s now influencing company strategy, appearing on podcasts, and being sought out by colleagues across departments. The first person to raise their hand gets this opportunity.
B) Rapid tool experimentation beats careful selection.
Rather than spending months evaluating one tool, Brian’s approach was to create a fast-track approval process for trying many tools. This allowed the team to discover what actually worked through hands-on experience rather than theoretical evaluation.
C) AI can reignite designers’ imagination muscle.
Years of “minimum viable product” thinking has trained designers to self-censor their creative ideas. AI’s ability to quickly prototype ambitious concepts (like animated characters waving in an intro screen) lets designers think beyond constraints again—leading to more delightful products.
