How Product Leaders Should Use AI, with Webflow CPO Rachel Wolan

In this podcast episode, Aakash Gupta interviews Rachel Wolan, the Chief Product Officer at Webflow, about AI product leadership. Rachel shares her workflows using Claude Code and Cursor to enhance productivity and demonstrates how she built her agentic chief of staff. She discusses the concept of ICCPO, which means a leader should be able to get their own answers to practically any question, and how to set up an organization to work in an AI-native way, including providing access to tools, supporting the team with training, and creating the right incentives. Rachel also shares insights on shipping AI-native features, emphasizing the importance of having great evals, playing off strengths, and thinking about distribution first, particularly in the context of answer engine optimization (AEO).