In an era where artificial intelligence is rapidly rewriting the rules of corporate software development and product management, Expedia Group is undertaking a major structural reorganization. The travel technology giant has eliminated eight senior leadership roles, including a key senior vice president and seven vice presidents. The move represents a fundamental pivot in how the company coordinates its massive technology apparatus, shifting power away from traditional, top-heavy management layers and toward smaller, highly agile, AI-focused engineering squads.
According to an internal company memo obtained by GeekWire, the high-profile departures include Sachin Singh, Expedia’s Senior Vice President of Book-to-Trip Technology. Alongside Singh, seven other vice presidents who oversaw critical operational domains—specifically payments, fraud and risk, and customer self-service tools—are also exiting the company.
Rather than hiring direct replacements for these outgoing executives, Expedia is redistributing their extensive portfolios. The responsibilities previously held by these eight leaders will be divided among the remaining technology executives, the Chief Information Security Officer (CISO), and the finance division.
This restructuring marks a significant milestone in Expedia’s ongoing effort to streamline its operations. By dismantling layers of coordinating middle management, the company aims to empower smaller, autonomous teams that can build, test, and deploy products much closer to the individual consumer brands they support, such as Vrbo, Hotels.com, and Expedia itself.
Dismantling the Coordination Layer: Who is Leaving and Where the Roles Go
The departure of Sachin Singh and seven vice presidents represents a notable reduction in Expedia’s executive headcount. Singh, who led the book-to-trip technology division, was responsible for the critical software architecture that connects the initial booking phase of a traveler’s journey to the actual trip execution. This division ensures that reservation data, itinerary management, and real-time travel updates flow seamlessly across Expedia’s various consumer-facing applications.
The seven departing vice presidents managed some of the most transaction-heavy and sensitive areas of the company’s platform:
- Payments: The underlying infrastructure that processes billions of dollars in global travel bookings annually, handling currency conversions, merchant relations, and payout distributions.
- Fraud and Risk: The defensive systems designed to protect both the platform and its users from cyber threats, identity theft, and financial chargebacks.
- Self-Service Tools: The automated customer service systems, chatbots, and help centers that allow travelers to cancel, rebook, or modify their itineraries without needing to speak to a human agent.
Instead of maintaining dedicated, high-level executives to oversee each of these verticals independently, Expedia is consolidating these functions. By transferring these responsibilities to the remaining tech executives, the CISO, and the finance department, the company is attempting to break down organizational silos.
For instance, aligning fraud and risk more closely with the Chief Information Security Officer consolidates the company’s defensive posture under a single security umbrella. Meanwhile, moving certain aspects of payments under the purview of the finance division reflects a desire to align transactional technology more directly with corporate financial operations.
The Scale of Expedia’s Tech Engine
To understand the magnitude of this reorganization, one must look at the sheer size of Expedia Group’s workforce. According to the company’s most recent annual report, Expedia employs approximately 16,000 people globally. Roughly half of that workforce—about 8,000 employees—operates within the product and technology group.
In previous disclosures and conversations with Skift, Expedia estimated that approximately 5,000 of those 8,000 tech employees are software engineers. Managing an engineering organization of this scale requires immense coordination. Historically, large technology companies have relied on hierarchical structures, where layers of vice presidents and directors coordinate roadmaps, manage dependencies, and ensure that different engineering teams do not build redundant systems.
However, as tech organizations grow, this coordination layer can often become a bottleneck. Decision-making slows down, product releases require endless cross-departmental approvals, and engineering teams find themselves isolated from the end-users and consumer brands they are supposed to serve. By eliminating eight senior roles, Expedia is signaling that it no longer requires the same level of top-down administrative coordination to keep its 5,000 engineers aligned.
The AI Paradigm Shift: Why "Squads" are Replacing Executives
The driving force behind this organizational shakeup is the transformative power of artificial intelligence. In the internal memo, Chief Product Officer Shilpa Ranganathan and Chief Technology Officer Ramana Thumu made the company’s motivations clear, writing that "AI has radically changed what’s possible."
Legacy Model: High Coordination Overhead
[Executive Leadership] ──> [VPs / Coordinating Layers] ──> [Siloed Tech Teams] ──> [Brands]
New Model: Decentralized AI-First Squads
[Executive Leadership] ──> [Autonomous AI-Enabled Squads] ─── Direct Integration ───> [Brands]In a traditional software development lifecycle, building a new feature—such as an automated refund tool or an advanced fraud detection algorithm—required extensive cross-team collaboration. A product manager would write a specification, which would then be reviewed by various security, payment, and database teams, overseen by coordinating vice presidents, before a single line of code was written.
Generative AI and advanced machine learning models have fundamentally altered this dynamic in several key ways:
1. Accelerated Code Generation and Deployment
With AI-assisted coding tools, individual engineers can write, test, and debug code at a fraction of the time it used to take. This reduces the need for large, specialized engineering departments that require dedicated executives to coordinate their outputs.
2. Automated Fraud and Risk Mitigation
In the past, managing fraud and risk required large teams of analysts and engineers constantly updating static rules. Today, AI models can analyze transaction patterns in real-time, automatically adapting to new threats without requiring constant manual intervention or executive oversight.
3. Intelligent Self-Service Systems
The integration of Large Language Models (LLMs) has revolutionized customer self-service. Rather than building complex, rigid decision trees for customer service portals, conversational AI engines can understand natural language queries, retrieve booking data, and resolve customer issues autonomously.
By leveraging these AI capabilities, Expedia can transition to a "squad" model. Under this framework, smaller, multi-disciplinary teams of engineers, product designers, and data scientists work autonomously. These squads do not need to wait for approvals from a centralized chain of command; instead, they are embedded directly within the brands they support, allowing them to iterate quickly and deliver localized solutions to travelers.
Aligning Technology with Consumer Brands
Expedia Group’s portfolio includes some of the most recognizable names in travel, including Expedia, Vrbo, and Hotels.com. Over the past several years, the company has undergone a massive, multi-year technical migration to consolidate these disparate brands onto a single, unified backend platform.
Prior to this consolidation, each brand operated on its own legacy technology stack, leading to massive redundancies. A developer building a search tool for Vrbo could not easily share that code with a developer working on Hotels.com.
Now that the core platform unification is largely complete, Expedia is entering its next strategic phase. The goal is no longer just platform consolidation, but brand-level optimization.
By shifting authority away from coordinating executives and toward smaller squads, Expedia is ensuring that its engineering talent is positioned closer to the actual consumer products. A squad dedicated to Vrbo, for instance, can focus entirely on the unique needs of vacation rental travelers and hosts, utilizing the shared AI-powered infrastructure of the parent company without being bogged down by corporate-wide bureaucracy.
The Road Ahead for Expedia’s Tech Strategy
As Expedia Group navigates this transition, the broader travel technology landscape will be watching closely. The online travel agency (OTA) sector is highly competitive, with rivals like Booking Holdings and Airbnb also investing heavily in generative AI to capture traveler loyalty and improve operational efficiency.
Expedia’s decision to streamline its leadership ranks and lean into AI-focused squads is a bold bet on the future of software engineering. By reducing the administrative overhead associated with managing an 8,000-person product and technology division, the company is attempting to reclaim the agility of a startup while maintaining the scale and reach of a global travel giant.
Ultimately, the success of this reorganization will be measured by how quickly Expedia can deliver new, AI-driven experiences to travelers, how effectively its remaining leaders can absorb their expanded portfolios, and whether these decentralized squads can maintain the security, reliability, and financial integrity of the company’s global travel platform.
