The CMO Podcast – Expedia × Profound | Competing in an AI-Driven Search World

Date: February 4, 2026
Host: Jim Stengel
Guests: James Cadwallader (Co-founder & CEO, Profound) & Daniel Shin Un Kang (Head of Organic and Agentic Search, Expedia)

Episode Overview

In this engaging episode, Jim Stengel explores the seismic shift in marketing brought by AI-powered search and agentic technologies. The conversation features James Cadwallader, CEO of Profound—a startup focused on helping brands navigate AI-driven discovery—and Daniel Shin Un Kang, who leads organic and agentic search at Expedia. They delve into transforming online visibility from serving people directly to serving machines acting on behalf of people, explaining the implications for brands, marketers, and marketers’ organizations. The discussion is framed as a real-world case study on how Expedia partners with Profound to stay ahead in AI-powered search and content.

Key Discussion Points & Insights

1. How Did James and Daniel Meet? (04:41–06:57)

• Daniel was aware of James and Profound through the San Francisco tech community. Connection began as Daniel sought to answer, “How are we really doing in AI search?” (04:51)
• Daniel describes the complex nature of measuring visibility in AI-driven search because little ground-truth data exists:
  “It’s actually quite complex for a couple reasons... Unlike traditional search, you don’t actually get a lot of data services or ground truth.” [05:58 – Daniel]

2. The Genesis of Profound (14:43–21:32)

• James recounts the early days of Profound when the AI-content paradigm shift wasn’t widely recognized:
  “It was a very non-obvious idea... It was almost overwhelming at the time to realize. It was like, wait, surely not. This can't be.” [16:12 – James]
• Identifies the central insight: Click-based search is obsolete; the only thing that matters is “how AI talks about your brand.”
  “In a world where you can talk to the internet and it talks back to you... the only thing that will matter to marketers is how AI talks about your brand.” [17:59 – James]

3. Personal Reflections on the Startup Journey (21:45–22:52; 24:05–27:18)

• James: Describes the startup grind as “the most fun I’ve ever had. I don’t want it to stop.” [21:52]
• Daniel: Candidly discusses the pain of shutting down an earlier startup, themes from his book (“Super Upside Factor”), and the opportunities to apply “venture math” and strategic thinking at Expedia. [24:22]

4. Building for an AI-Driven World: The Expedia × Profound Partnership (27:18–42:30)

• Daniel details the business problem: maximizing Expedia’s brand visibility in AI search and answer engines, which requires new methodologies for synthetic querying and content optimization.
  “You want to know how much, where you are showing up, when you're not showing up, and then constantly optimize your stuff to be able to go do that.” [30:56 – Daniel]
• Technical sophistication: Profound must work at the scale of “hundreds of millions of assets.” [36:27 – Daniel]
• James highlights that the shift means “marketing to machines,” requiring technology to measure and optimize at a scale and context never before possible:
  “You are creating—marketing to machines. Really. That’s the idea.” [35:10 – James]
• Sentiment matters: AI-generated answers insert qualitative opinions about brands, and Profound tracks both presence and tone of mentions:
  “...you’re getting an opinion for free. And that opinion varies and evolves over time.” [38:38 – James & Daniel]

5. Tactical & Strategic Advice for Marketers (46:21–50:58)

• Daniel:
  1. Think in terms of portfolios—AI organic, agentic commerce, ads, etc.—not just AEO (answer engine optimization).
  2. Prepare for a range of “probable future states,” since platforms are rapidly evolving.
     “If you can't get AEO, good luck getting everything else. But you have to think of it as a portfolio...” [46:53 – Daniel]
• James:
  1. “Go find whoever was running your SEO, give them a pay rise.”
  2. This is now an ongoing, never-done function in the marketing stack, not a “one and done” project.
     “SEO could become mega sexy... Lean in and empower that team.” [49:16 – James]

6. The Future of Advertising in an AI World (50:58–54:32)

• James:
  “Generative ads will be the biggest unlock in marketing history... Generative, multi-turn conversational interface, you understand such rich context and intent. Advertising is going to be so wonderful.” [51:15 – James]
• Daniel:
  Notes the challenge of extracting intent from conversational noise and stresses the complexity of ad targeting in AI conversations. Predicts new ecosystems will emerge with both large and long-tail players. [52:29]

7. Personal Journeys: Education and Motivation (54:34–57:33)

• Daniel: Traditional education as a way to raise his “base case” and open opportunities.
• James: Entrepreneurial since age 18, “at war with my helmet on,” sometimes wonders about traditional academic paths but is confident in his choices.

8. The First Brand that Inspired Them (57:33–59:26)

• James: Adidas and David Beckham’s soccer boots:
  “Can just remember it being so visceral, like it was needed to own that pair of football boots. Nothing else mattered in my world at the time.” [58:01 – James]
• Daniel: Apple, discovered in rural Canada, symbol of possibility and creativity:
  “I finally got to use some Apple products. I'm very happy.” [58:48 – Daniel]

Notable Quotes and Moments

• On the AI shift in marketing:
  “We’re not building content anymore for human beings. We’re building content for user agents on behalf of consumers.” [34:22 – Jim quoting James]
• On founding Profound:
  “...this is the biggest outcome in the history of capitalism. Surely not. And why is no one talking about this?” [16:12 – James]
• On measuring brand visibility in AI:
  “That’s the new click: when a user agent visits.” [42:54 – James]

Important Timestamps

• [04:41] – How James & Daniel met / context of partnership
• [14:43] – Profound’s founding story and the AI shift
• [21:52] – James reflects on the journey
• [24:22] – Daniel’s personal startup journey & joining Expedia
• [27:59] – Case study: What Profound & Expedia are actually doing
• [35:10] – Marketing to machines explained
• [38:38] – Sentiment in AI search and its significance
• [46:21] – Strategic advice for CMOs
• [51:15] – The future of generative AI advertising
• [54:34] – Education and life choices
• [57:33] – First brand memories
• [61:24] – Final actionable advice to CMOs

Actionable CMOs Advice (61:24–62:30)

James:

• “Go to the people who run search for you and get to know how you're going to show up in this new world of AI and creating content for machines on behalf of people. This is the biggest platform shift in the history of marketing and you should invest accordingly.”

Daniel:

• “You won’t have the bandwidth to deep-dive yourself. Empower someone on your team to go deep, coordinate, and bring the results back. Let them run.”

Takeaway

Learn about and prioritize this profound shift in marketing—the move to AI-driven content and machine-to-machine brand engagement. Understand its impact, empower your teams, and invest strategically in this new paradigm.

Listen at: CMO Podcast YouTube Channel
Learn more about Profound: www.tryprofound.com

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