Expedia Group is making a bold, uncomfortable pivot. The Seattle-based online travel giant told its product and technology teams on Tuesday that it is parting ways with at least eight vice presidents and senior vice presidents as part of a sweeping reorganization centered on artificial intelligence. In an internal memo obtained by GeekWire, Chief Product Officer Shilpa Ranganathan and Chief Technology Officer Ramana Thumu framed the moment in almost existential terms. “AI has radically changed what’s possible,” they wrote. “Work that once took weeks increasingly happens in hours.” To fully realize that opportunity, they argued, the company must “fundamentally change how we work, how we’re organized, and the technology we build.” The answer, in their view, is a move to “small end-to-end squads with clear ownership,” with AI and machine learning woven into every mission rather than treated as a separate specialty. For employees, the memo promises less time spent coordinating and waiting, and more time building products for travelers and partners. But it also brings a human cost. The changes ripple through leadership ranks, shifting reporting lines, expanding some portfolios, shrinking others, and eliminating a small number of roles. The company’s spokesperson said the impact is “limited” and that most affected employees are moving to different teams. Still, the reorg is a clear signal: after 30 years, Expedia is not content to let the AI era catch it by surprise. The memo reads like a declaration that the old way of doing things—large teams, tangled hierarchies, slow handoffs—is no longer viable. For the roughly 8,000 people in Expedia’s product and technology organization, the message is both exciting and unsettling. The future they’ve been hired to build is arriving faster than expected, and it is rewriting the org chart beneath their feet. The company’s leaders are betting that speed and ownership will matter more than tenure and title, and that AI can bridge gaps that used to require layers of management. For the leaders who are leaving, it is a reminder that even executives who helped steer the company through previous disruptions can be caught in the current’s turn.
The most senior departure is Sachin Singh, SVP of book-to-trip technology, a former Amazon executive who joined Expedia in 2022 and was part of the CTO leadership team. The memo credits Singh with advancing priorities across checkout, payments, fraud prevention, servicing, and AI. But in the new structure, his portfolio is being carved up. Fraud and risk moves under Chief Information Security Officer Hilik Kotler. Self-service moves under Ryan O’Neill. Payments product, technology, and operations moves under Reena Patil and Debashis Saha, with strategic payment partnerships shifting to finance. Saha, in turn, is being promoted to senior vice president of travel foundations. The other leaders leaving are Sara Beckmann, Ian Butcher, Matt Esler, Amitabh Ghosh, Emil Riccardi, Fiona Stevenson, and Shao Xie—all vice presidents in product and technology roles spanning pricing, lodging, data platforms, and travel platform and fraud. Their names may not be familiar outside the company, but their work shaped the systems that millions of travelers use to compare prices, book stays, and manage trips. Alongside the departures, Expedia is promoting from within. Rajat Arora, Ryan Hillman, Ashwita Kaur, and Ambrish Srivastava are all moving up to vice president. The reorg also consolidates dedicated technology teams under brand product leaders CJ Allen, Ritcha Ranjan, and Eric Moore, bringing engineering closer to the brands and businesses they support. Supply product and technology consolidates under Jonathan Holland. Data, AI, and agentic platforms are consolidated under Xavier Amatriain, the former Google AI executive who joined Expedia in December as its first chief AI and data officer. Rick Fast, previously senior vice president of platform engineering, becomes chief architect. The memo says most changes are about leadership scope and reporting lines, not headcount. But the handful of eliminated roles is a reminder that reorganizations, however strategic, land on real people. Expedia is betting that smaller, autonomous squads with clear ownership will unlock the speed that larger hierarchies cannot.
The reorganization is happening against a backdrop of real anxiety in the online travel industry. AI agents are emerging as a new interface for travel, capable of researching flights, booking hotels, and managing itineraries with little more than a text prompt. That raises a disturbing possibility for Expedia and its competitors: AI assistants could do to them what they once did to traditional travel agents. Instead of travelers visiting Expedia or Booking.com, they might simply ask ChatGPT or a future AI assistant to handle everything, leaving the big booking platforms as invisible inventory sources in the background. Marriott’s CEO, for one, has said AI booking agents will hurt online travel agencies more than hotels. Expedia’s CEO Ariane Gorin, speaking in May on the company’s 30th anniversary, described AI as the third major technology disruption in Expedia’s history, after the internet and mobile, and said the era is “only starting to unfold.” So far, the threat has been slower to materialize than some feared. In March, OpenAI pulled its Instant Checkout button from ChatGPT’s main interface and stepped back from processing travel transactions directly. When that happened, shares of Expedia and Booking Holdings jumped significantly—a small window into how much of their future valuation is tied to the fear of AI disintermediation. But the reprieve is likely temporary. The same technology that powers instant answers, personalized recommendations, and automated customer service is also improving at breakneck speed. Every quarter, AI models become better at understanding nuance, comparing options, and completing transactions. The window for Expedia to position itself as an essential partner in the AI ecosystem—rather than a middleman to be bypassed—may be narrow. This is why the company is not just reorganizing internally; it is also embedding itself in the new platforms. It was a launch partner when OpenAI opened ChatGPT to outside apps, and it has begun buying ads inside ChatGPT. These are early, experimental bets, but they signal that Expedia wants to be wherever travelers are, even if that means sharing the spotlight with an AI assistant.
At the heart of the reorg is a bet on how work should get done. The memo describes experiments with “a different way of working” that removes usual constraints and gives smaller cross-functional teams clear ownership. The lessons learned from those pilots are straightforward: speed blockers are often structural; decisions and accountability work best when teams are close to the work; and AI, when used well, can bridge gaps and scale knowledge in real time. These may sound like management platitudes, but they reflect a genuine shift in how product development happens at scale. Historically, a company like Expedia built travel platforms through large, specialized departments—one team for payments, another for pricing, another for fraud—each with its own priorities and timelines. Coordination across those silos consumed enormous amounts of time. The new model tries to collapse that distance. Small end-to-end squads are meant to own a problem from start to finish, with the authority to make decisions and the tools to move quickly. This is a deeply human change as much as a technical one. It changes what it feels like to come to work. Instead of waiting for approval from several layers of management, engineers and product managers are expected to act. Instead of writing handoff documents, they are expected to work alongside designers, data scientists, and business leaders in the same room, even if the room is virtual. And instead of treating AI as a separate platform, they are expected to make it part of every mission—using machine learning to improve search results, surface unseen travel options, respond to customer questions, and catch fraud before it happens. For some employees, this is energizing. For others, it is disorienting. The leadership changes are a reminder that the company is willing to make painful decisions to move in this direction. The old structures produced reliable, incremental improvements; the new ones are designed for speed and invention.
Expedia Group is not a small company. Its portfolio includes Expedia, Hotels.com, Vrbo, Orbitz, Travelocity, ebookers, Wotif, and a majority stake in trivago. At the end of 2025, it had about 16,000 employees across nearly 50 countries, and roughly half of those people work in technology roles. That makes the product and technology organization touched by Tuesday’s memo a workforce of about 8,000—a major tech operation in its own right. But the company has been through dramatic swings in size before. Employment peaked above 25,000 in 2019, fell to 14,800 during the pandemic when travel nearly vanished, and rebounded to about 17,100 by the end of 2023. Since then, a series of restructurings and layoffs have kept the number in flux. Each of those numbers represents real people: engineers who moved across the country for a job, designers who built their careers around travel, managers who spent years navigating Expedia’s complex matrix of brands and platforms. Layoffs and reorganizations have become almost routine in the tech industry, but that doesn’t make them any easier for the people who lose their roles or who watch colleagues walk out the door. The company’s spokesperson described the current changes as “limited” and said most affected employees are moving to different teams. But the elimination of even a small number of roles in a company this size sends a ripple through the culture. Employees are left to wonder whether their own jobs are safe and whether the promise of AI-driven efficiency might eventually make their skills less necessary. The leadership’s answer, embedded in the memo, is that AI is not a reason to shrink the organization but a reason to rebuild it—so that human talent can be deployed more creatively and with more autonomy. Whether that promise holds will depend on execution.
What makes this moment different from earlier restructurings is the sense that the ground itself is shifting. Expedia has navigated disruption before—the rise of the internet, then mobile—and emerged as a dominant force in online travel. But AI has the potential to change the relationship between travelers and the platforms they use. Instead of beginning a search on Expedia, travelers may begin with a conversation with an AI assistant that already knows their preferences, their budget, and their calendar. The booking platform becomes just one of many options in a machine’s decision-making process. That is why the internal changes are so important. Expedia is trying to make itself a partner to artificial intelligence rather than a victim of it. It is embedding its services into tools like ChatGPT, buying ads where travelers are already asking questions, and putting its AI leadership at the center of the organization. It is also trying to change its own culture, breaking down the silos that made large companies slow and bureaucratic. The executives who remain are asking employees to trust that smaller teams, clear ownership, and AI-assisted workflows will create more satisfying work and better outcomes. It is a compelling vision, but it is also an experiment. The next few years will show whether Expedia can move fast enough to keep pace with companies like OpenAI, Google, and a wave of startups that see travel as a rich vein for AI innovation. For the leaders who are leaving, the departure is a personal loss, even if the company frames it as a strategic necessity. For those staying, the work ahead is harder and less certain. But there is also something hopeful in the memo’s tone: a recognition that the old ways cannot hold, and that the only way through is to change, learn, and build together. Expedia’s next chapter is being written now, not by a single visionary, but by thousands of engineers, designers, and product managers trying to figure out what it means to make travel easier in an age of intelligent machines.
