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In this edition of Expedia Group Arrivals, we’re excited to introduce you to Daniel Shin Un Kang, Head of Organic and Agentic Search based in the Seattle office. He brings deep expertise in technology and venture capital, previously serving as a growth equity investor at SoftBank Vision Fund and as the CEO and Co-founder of a Y Combinator–backed fintech startup. Daniel also sat on the Board of Auto1 Group, Europe’s largest used-car marketplace, advising their pre-IPO raise and retail strategy.
Daniel now applies his expertise to scale our organic and agentic search and recently launched Business to Agent marketing capabilities to influence AI agents.
Daniel Shin Un Kang | Head of Organic and Agentic Search | Seattle, WA, U.S.
Tell us about your journey – what led you to a career in travel technology?
I originally trained to be a pilot sponsored by the Canadian government. Financial and physical limits forced me to pivot, which was when I went to study at McGill University.
I started my career as a consultant at Oliver Wyman, and from there built my career with a thread of democratizing opportunities. At SoftBank Vision Fund, I saw how technology and capital scale impact while investing in fintech companies that democratized financial access. Shortly after, I wanted to directly create financial access, and started my own company backed by Y-Combinator in my dorm room at the University of Oxford. After three years of building that business to help creators and freelancers access funding and financial services, I wrote a book called The Super Upside Factor with Wiley & Sons, which explores how to build a portfolio of asymmetric bets with outsized potential.
Today at Expedia Group, I lead Organic and Agentic Search, with global responsibility for our organic and agentic revenue. What drew me here was the chance to build at scale inside a platform with real structural advantages and to help shape how travelers discover and engage with our brands in a fast-changing search landscape.
What has been the catalyst for your career growth?
I’ve been running the same playbook since I was 17: Asymmetric Principles.
I grew up on a farm in a low-income, immigrant family in a Canadian town of 3,000. College wasn’t affordable, and part-time work at $10 an hour was never going to close the gap. But a single scholarship could be worth $10,000 – so I applied for more than 120. I was rejected 80% of the time. The 20% that landed paid for my education.
The pattern repeated at every fork. Oliver Wyman to SoftBank, I was the underdog candidate and kept knocking until a Partner took the bet. Starting my company, I was rejected 166 times before ultimately raising millions with Y Combinator.
The underlying idea stays the same: you don’t need every bet to work. If you budget for a high failure rate, take swings where the upside is spectacular, and learn from every iteration, you build a portfolio of attempts that compounds your surface area for luck.
A byproduct of operating this way is that I’ve gotten comfortable being the least experienced person in the room – sitting on the Auto1 Group board across from people who’d run businesses far longer than I’d been working. In those rooms, I created value by outworking the prep and offering new angles their tenure makes harder to see – in areas of change. These experiences give me an unfair advantage at frontiers like agentic search, where industry experience is an edge, not a moat. The rules are still being written.
What kind of culture are you aiming to cultivate on your team?
We’re building to become the number one agent marketer in the world — to reach, influence, and serve AI agents better than anyone else. That’s the bar.
The team runs on velocity and scale. We’re scaling proven winners in organic and agentic search, and placing bets on what’s next across technical, infrastructure, and content work. The space is being defined in real time, and the teams that define it won’t be the ones with the most polished plans — they’ll be the ones shipping, learning, and compounding wins week after week.
I hire for winner’s energy. People who want to compete, keep score, and get more energized when the stakes go up. High agency. High tolerance for failure. Comfortable moving outside traditional role boundaries because the boundaries haven’t been drawn yet.
There aren’t many places where a focused team can credibly aim to be the best in the world at something. This is one of them.
How would you describe your Leadership Style?
You hire great people for their judgement, not to tell them exactly what to do. Early on, my job is to understand how someone thinks and decides — what they’ll catch that I’d miss. Once I have that, I want them running their work with real ownership.
That doesn’t mean stepping back. I set the direction, own the outcome, stay close to the calls where I can add the most value, and run air cover so the team isn’t slowed down by things that aren’t theirs to solve.
Where did you travel most recently, and what destination is next on your list?
The travel I care most about is the kind I take every year – one trip with a group of college friends, one with family. They’re the things on the calendar that don’t move. I think of it as memory compounding: the same group, the same ritual, in a different place each time. Over enough years you end up with a real archive of them.
This year’s friend trip is Iceland – somewhere we’ve wanted to go for a while. I’ve made it to 46 countries so far, mostly chasing the iconic stops, but the trips I remember best aren’t the ones I picked off a list. They’re the ones I keep taking.
Join us to build the world of travel.
Ready to build what’s next in travel tech? Explore open opportunities at Expedia Group and join us in shaping the future of travel.