I stole the AI product stack of the top 1% product managers for you (full tutorial)

Rachel Wolen is CPO at Webflow ($4B company). She runs her whole day out of Claude Code and Cursor. She reveals how to build an agentic Chief of Staff (calendar, email, analytics agents), scale AI adoption from 0% to 30% with Builder Days, and ship AI-native features with MVO before MVP and proper evals. Full Writeup: https://www.news.aakashg.com/p/rachel-wolan-podcast Transcript: https://www.aakashg.com/ai-product-leadership-rachel-wolan-claude-code-cursor/ ---- Timestamps: 0:00 - Intro 1:30 - What Is IC CPO? 3:25 - Building Agentic Chief of Staff 7:03 - Calendar Agent Demo 9:30 - Email Triage Agent 13:01 - Linear Ad Start 13:48 - Analytics Agent (Snowflake + MCP) 17:27 - Linear Ad Start 19:26 - Building Agent from Scratch 29:16 - Setting Up Your Org for AI 34:25 - Shipping AI-Native Features 36:12 - Evals Story 40:58 - Distribution First Mindset 44:00 - Outro ---- 🏆 Thanks to our sponsor: Linear: Plan and build products like the best - https://linear.app/partners/aakash ---- 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 similar prototypes. Director caught early: "Go harmonize your prototypes now." Easier now than late in product cycle. 8. MVO before MVP framework - Most teams: Feature → PRD → Design → Ship. Rachel flips it. MVO (Minimal Viable Output) before MVP. Get model's output right FIRST using RAG, prompt engineering, context engineering. Only then build feature. "If you don't have desired outputs, don't spend time productizing the AI feature." 9. Evals are now your job - Brutal story: Webflow's AI app generator 2 weeks from launch. Rachel tested it. Agent kept dying. Realized: changed underlying model, evals didn't have coverage. Evals = test cases for models. Want dream evals (should pass) and edge cases (should fail). Use BrainTrust. Teaching PMs to write evals is part of AI PM toolkit now. 10. Build on your strengths - Framework: See trend → Is it applicable to customers? → What's YOUR core competency? Webflow's strength: bringing visitors to front door via CMS. Built production-grade app generator (not prototype like Lovable). Uses your brand, CMS, hosting, security. "We're bringing a way to prompt an app to production." Don't copy trends, leverage unique strengths. ---- 👨‍💻 Where to find Rachel Wolen: LinkedIn: https://www.linkedin.com/in/rachelwolan/ Twitter/X: https://x.com/rachelwolan Website: https://www.rachelwolan.com/ 👨‍💻 Where to find Aakash: Twitter: https://www.x.com/aakashg0 LinkedIn: https://www.linkedin.com/in/aagupta/ Newsletter: https://www.news.aakashg.com #aipm #claudecode #productmanagement ---- 🧠 About Product Growth: The world's largest podcast focused solely on product + growth, with over 200K+ listeners. 🔔 Subscribe and turn on notifications to get more videos like this.

Rachel WolenguestAakash Guptahost

Nov 30, 202545mWatch on YouTube ↗

EPISODE INFO

Released: November 30, 2025
Duration: 45m
Channel: Aakash Gupta
Watch on YouTube: ▶ Open ↗

EPISODE DESCRIPTION

Rachel Wolen is CPO at Webflow ($4B company). She runs her whole day out of Claude Code and Cursor. She reveals how to build an agentic Chief of Staff (calendar, email, analytics agents), scale AI adoption from 0% to 30% with Builder Days, and ship AI-native features with MVO before MVP and proper evals. Full Writeup: https://www.news.aakashg.com/p/rachel-wolan-podcast Transcript: https://www.aakashg.com/ai-product-leadership-rachel-wolan-claude-code-cursor/ ---- Timestamps: 0:00 - Intro 1:30 - What Is IC CPO? 3:25 - Building Agentic Chief of Staff 7:03 - Calendar Agent Demo 9:30 - Email Triage Agent 13:01 - Linear Ad Start 13:48 - Analytics Agent (Snowflake + MCP) 17:27 - Linear Ad Start 19:26 - Building Agent from Scratch 29:16 - Setting Up Your Org for AI 34:25 - Shipping AI-Native Features 36:12 - Evals Story 40:58 - Distribution First Mindset 44:00 - Outro ---- 🏆 Thanks to our sponsor: Linear: Plan and build products like the best - https://linear.app/partners/aakash ---- 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.
1. 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.
1. 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.
1. 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.
1. 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.
1. 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.
1. 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 similar prototypes. Director caught early: "Go harmonize your prototypes now." Easier now than late in product cycle.
1. MVO before MVP framework - Most teams: Feature → PRD → Design → Ship. Rachel flips it. MVO (Minimal Viable Output) before MVP. Get model's output right FIRST using RAG, prompt engineering, context engineering. Only then build feature. "If you don't have desired outputs, don't spend time productizing the AI feature."
1. Evals are now your job - Brutal story: Webflow's AI app generator 2 weeks from launch. Rachel tested it. Agent kept dying. Realized: changed underlying model, evals didn't have coverage. Evals = test cases for models. Want dream evals (should pass) and edge cases (should fail). Use BrainTrust. Teaching PMs to write evals is part of AI PM toolkit now.
1. Build on your strengths - Framework: See trend → Is it applicable to customers? → What's YOUR core competency? Webflow's strength: bringing visitors to front door via CMS. Built production-grade app generator (not prototype like Lovable). Uses your brand, CMS, hosting, security. "We're bringing a way to prompt an app to production." Don't copy trends, leverage unique strengths. ---- 👨‍💻 Where to find Rachel Wolen: LinkedIn: https://www.linkedin.com/in/rachelwolan/ Twitter/X: https://x.com/rachelwolan Website: https://www.rachelwolan.com/ 👨‍💻 Where to find Aakash: Twitter: https://www.x.com/aakashg0 LinkedIn: https://www.linkedin.com/in/aagupta/ Newsletter: https://www.news.aakashg.com #aipm #claudecode #productmanagement ---- 🧠 About Product Growth: The world's largest podcast focused solely on product + growth, with over 200K+ listeners. 🔔 Subscribe and turn on notifications to get more videos like this.

SPEAKERS

Rachel Wolen
guest
Chief Product Officer at Webflow, discussing AI-native product leadership and agentic workflows.
Aakash Gupta
host
Product-focused creator and host who runs a paid newsletter and interviews product leaders about AI tooling and workflows.

EPISODE SUMMARY

In this episode of Aakash Gupta, featuring Rachel Wolen and Aakash Gupta, I stole the AI product stack of the top 1% product managers for you (full tutorial) explores webflow CPO’s AI agent stack for elite product leadership today The “IC CPO” mindset is framed as a leader’s ability to self-serve answers by investing in high-quality, accessible data and modern AI tooling across the team.

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