Greg Schulze, Expedia Group’s chief commercial officer for 21 years, is leaving the company this month, closing a chapter that fundamentally altered one of the world’s largest travel platforms. His exit arrives during a period of sweeping industry change—one he helped steer through major disruptions, from the mobile booking revolution to the pandemic’s abrupt halt of global travel.
Schulze joined Expedia in 2005, when online travel was still fighting skepticism about its reliability. By May 2026, under his leadership, the company had booked more than a trillion dollars in gross bookings over his tenure—a milestone he downplayed in favor of the broader transformation. “I’m confident that Expedia was changed by what I brought every day,” he told me, carefully sidestepping the word “legacy” because “that sounds arrogant.” His focus remained on the impact: on employees, partners, and the industry as a whole.
His career began in data analytics, where he honed skills in revenue management and deal optimization. Yet he soon recognized that the most effective outcomes came not from aggressive negotiation but from understanding people—leaving them convinced they had won. Early airline partnerships tested this approach, with some negotiations turning heated and public.
By combining data-driven constraints with an engineer’s problem-solving, he converted potential adversaries into long-term collaborators. “I realised that the combination of my understanding of revenue management and belief in the power of relationships and understanding people allowed us to work through really difficult negotiations that were quite emotional and publicly combative,” he said, adding with quiet satisfaction, “and then to have remained friends with these partners all these years.”
This ability to merge analytical precision with relationship-building became the foundation of his leadership. Over two decades, he scaled his approach across Expedia’s global operations. His departure now places the company at another turning point, one he likens to the desktop-to-mobile shift, but even more significant.
AI Redefines Travel’s Future Rules
Artificial intelligence, Schulze argues, is rewriting travel’s core rules beyond mere automation. The transformation lies in how customers engage with the industry: shifting from static searches to dynamic, conversational interactions, even agent-assisted service. Meanwhile, the boundaries between business and leisure travel are fading. Airlines, banks, and loyalty programs now function as distributors, while events like sports tournaments account for 10% of total travel spending. This is not a fad but a permanent state of being.
Despite the upheaval, fundamental human motivations endure. People continue to travel, seeking connections, with destinations, with others, and with experiences. Schulze pointed to the industry’s resilience through crises: 9/11, the 2008 financial collapse, the pandemic. “At the core, people are still travelling and still looking to connect with people and places around the world,” he noted. “Planes are still full. The world may be ending, but apparently, we’re all flying to see it happen in person.”
Beyond Expedia: Identity and Unplanned Departures
The discussion turned to identity. After two decades at Expedia, Schulze rejected the notion that his professional life defined him entirely. “All of us are replaceable,” he observed. “This is a business that will continue past me. And yet the relationships that we have, the experiences that we have, are important parts of our lives.” His own identity, he explained, was shaped not just by Expedia but by earlier roles, a factory job that taught discipline, data work that sharpened his mind, and relationships that outlasted spreadsheets.
His time in Singapore stands out, including a chance meeting with a journalist over kaya toast. Yet his departure was sudden. The pandemic disrupted plans, his son graduating high school in a virtual ceremony, and a sudden departure that nobody had planned for. “It was quite surreal,” he said. Still, the recovery confirmed a truth he’d seen before: travel isn’t just resilient. It’s essential.
Schulze remains on Traveloka’s board, staying engaged with Asia’s travel market, and is exploring new opportunities that combine his analytical skills with interpersonal strengths. His daughter’s college graduation adds another layer to this phase.
Legacy of Trust in a Digital Age
The WiT Singapore conference, themed “21: A New Beginning”, held special meaning for Schulze. His departure from Expedia aligns with both the 20th anniversary of his arrival and the industry’s broader renewal. The event, running from September 30 to October 2, marks a moment of reflection on how the past two decades have transformed travel, from booking methods to customer experiences. Schulze, who joined Expedia when online transactions faced doubt, has spent his career bridging skepticism and trust. His exit coincides with an industry poised to redefine itself again, this time through artificial intelligence, a shift he compares to the mobile booking revolution of the 2010s.
The pandemic forced an early end to Schulze’s time in Asia, where he had spent years expanding Expedia’s presence. His son’s high school graduation, originally planned as an in-person celebration, became a virtual event, a moment he described as “surreal.” The crisis also accelerated existing trends, particularly the rise of digital interactions and the convergence of business and leisure travel. These changes, he emphasized, are permanent, reshaping how people plan and engage with travel.
His final months at Expedia were defined by both closure and anticipation. Schulze continues to engage with the industry through his Traveloka board role, where he interacts with Asia’s evolving travel market. He is pursuing additional board positions where his unique blend of analytical rigor and interpersonal skills can address key industry challenges. He was recognized as a WiT Warrior last year on the organization’s 20th anniversary for his efforts to strengthen Asia’s position in global travel.