About this episode
Today’s EpisodeThere are tons of tutorials about Claude Code and Cursor for IC PMs.But what about leaders?Today’s episode is a masterclass on both sides of AI product leadership. How to be a productive AI leader and how to ship AI-native features at scale.Rachel Wolan is the Chief Product Officer at Webflow, the $4 billion company powering TED Talks, SoundCloud, and Reddit.Rachel walks through building her agentic Chief of Staff live, sets up a LinkedIn post generator from scratch, and shares the brutal lessons from launching Webflow’s AI app generator.----Brought to you by:Linear: The task management platform dethroning Jira-----Key Takeaways:1. IC CPO means self-serving answers - "As a leader, you are able to get your own answers to practically any question." No waiting on data scientists. No back-and-forth with analytics. You have tools to self-serve insights, make analysis, automate workflows. Model behavior for your team to inspire them.2. Calendar agent analyzes time - Runs weekly with prompt: "Analyze my calendar for last two weeks. Where could I delegate?" Returns delegation opportunities, red flags (double bookings, context switching), what to cut next week. Rachel gives output to EA. Spot on when shown live.3. Email agent watches behavior - Complete inbox access. Runs triage, archives junk (calendar notifications, marketing), pins important messages, creates draft replies. Twist: watches behavior. If email sits too long, it notices. Caught meeting missing link. Rachel's rule: agent recommends, she approves. No autonomous sending.4. Analytics agent via MCP - Connected Claude Code to Snowflake via MCP servers (not officially supported repos, just fed them to Claude Code). Ask natural language questions, get SQL executed real-time. "How many sites does Shirts.com have?" Claude writes query, authenticates via SSO, returns answer. Data scientist in pocket.5. Accept the adoption curve - Your org follows standard curve: early adopters, early majority, late adopters, laggards. Create pathways for everyone to ascend ladder at their pace. Don't force everyone to be you. Rachel to team: "I only want to see prototypes when you have meetings with me." Creates culture investing in prototype quality.6. Builder Days strategy - Give everyone access: Claude Code licenses, MCP to Snowflake/Tableau, Figma Make, Cursor with design system. Run Builder Days where champions help others through technical hurdles. Everyone demos something outside comfort zone. Results: 0% to 30% of designers using Cursor weekly after first Design Builder Day.7. Rewrite career ladder - Webflow rewriting career ladder to make AI-native work an expectation, not nice-to-have. Create right incentives. Make sure people supported. Avoid AI for AI's sake. Example: Two designers built si
