Expedia × Profound | Competing in an AI-Driven Search World // With James Cadwallader and Daniel Shin Un Kang

We’re living through one of the biggest shifts in the internet since it began: a move from building content for people to building content for machines, on behalf of people. On this week’s episode, Jim Stengel is joined by James Cadwallader, Co-Founder and CEO of Profound, and Daniel Shin Un Kang, Head of Organic and Agentic Search at Expedia, for a thoughtful, practical conversation about AI search, answer engines, and what this shift means for the future of marketing.

James founded Profound in 2024, raising $60 million and earning recognition from Redpoint Ventures as one of the most promising private AI companies shaping applied artificial intelligence. Today, Profound works with brands like US Bank, Chime, Expedia, and DocuSign to help them navigate the transition from traditional search to a world of answer engines, agents, and AI-led experiences.

After building companies and investing in high-growth technology businesses, Daniel moved from the venture world into operating at global scale. He now leads Organic and Agentic Search at Expedia, where he’s helping redefine how one of the world’s largest travel platforms shows up in AI-powered search and discovery.

Together, James and Daniel unpack how brands actually appear inside AI systems like ChatGPT and Gemini, why traditional SEO metrics no longer tell the whole story, and how CMOs should rethink visibility, content, and measurement in an AI-driven world.

This episode offers a rare look at AI search from both sides of the table: the platform builder shaping the category and the operator putting it to work inside a performance-driven global brand. If you’re a CMO wondering what to focus on now, this conversation is a strong place to start.

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This week's episode is brought to you by Deloitte and the IAB.

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