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AI has collapsed the gap between idea and execution—but standing out in a flood of generative tools requires more than just speed. Product leaders now face a different kind of challenge: evaluating opportunities with sharper questions, building for users with evolving expectations, and navigating distribution channels that look nothing like they did a year ago. Rachel Wolan, CPO at Webflow, joins Hannah to unpack what it really takes to ship differentiated, production-ready AI products in a crowded market. Drawing from her experience leading product at Dropbox and now building an AI-native digital experience platform, Rachel shares how she approaches defensibility, user segmentation, AEO, and when to buy versus build. Resources from this episode: • Subscribe to The CPO Club newsletter (https://cpoclub.com/subscribe/) • Connect with Rachel on LinkedIn ( / rachelwolan ) and Twitter/X (https://x.com/rachelwolan) • Check out Webflow (https://webflow.com/)