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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.
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By Hannah Clark - The Product Manager4.8
66 ratings
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:

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