The Product Podcast Webflow CPO on How Product Leaders at AI-Native Companies Act as Individual Contributors | Rachel Wolan | E281
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Dec 23, 2025 
Rachel Wolan, Chief Product Officer at Webflow, discusses the company's transformation into an AI-native platform. She introduces the ICCPO framework and the importance of leaders using their own tools. The conversation delves into building AI-native products and the strategic shift from SEO to Answer Engine Optimization (AEO). Rachel also highlights innovative products like AppGen that enhance enterprise application generation, and her insights on leveraging AI for productivity make this discussion a goldmine for aspiring product managers.
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Lead By Building Your Own Tools
- Be patient zero: use and build with your own AI tools to understand limitations and shape vision.
- Ask questions yourself, prototype, then work backwards to what must be true to productize the solution.
AI Toolkit Defines The Product
- AI-native means the model toolkit is the product and must shape how you deliver value.
- Leaders must know the toolkit to place informed bets and guide teams effectively.
Building A Chief-Of-Staff AI
- Rachel iterated ~10 times building an agentic chief of staff before models became reliable for long tasks.
- Once Sonnet/Opus improved, she ran agents for podcast prep, email triage, analytics and calendar automation.