When Expedia Group's employee digital experience and learning teams started fielding employee requests for AI tools, the question was never simply which platform to buy. The deeper question was how to give people one clear place to start, without boxing them into a single, rigid experience for every kind of work.
Becky Wilson, who leads the employee digital experience team at Expedia Group, and Alex Buono, who leads AI enablement out of learning and development, led a session at Glean:GO 2026 to share how that thinking has played out in practice.
From personal experimentation to enterprise guardrails
When Expedia first began exploring AI tools across the workplace, employees began asking for enterprise access to the tools they were already using at home. From an IT standpoint, that meant guardrails. Expedia couldn't hand out licenses to every AI tool on the market, so the team started with the contracts it already had, embedding AI into Microsoft, Slack, and Zoom so people could get comfortable with the technology inside tools they already used every day. However, one piece was still missing: connectivity across the company's enterprise context. Without it, employees were still bouncing between tools and verifying sources to piece together an answer.
That gap led Expedia to run a formal RFP process, evaluating the maturity of AI platforms against two needs at once: strong enough security and governance for IT, and an approach that employees would actually trust and adopt. Glean stood out for how quickly it was adopted and how accurate it felt to users from day one, since it connected context they'd never had linked before.
Building an early-adopters cohort
Expedia built what it calls the "Pioneers Group": representatives from every business unit, given early access to new tools so they could stress-test them and shape how the rollout would be communicated to their peers. Getting that feedback early mattered, since asking people to add something new to their toolkit is inherently hard, and learning new habits doesn't come naturally.
The team at Expedia measured success less by usage numbers and more by a shift in behavior. When someone asked a colleague if they'd asked that question to Glean first before coming directly to the team, that was a signal that enablement was working. As the questions employees brought to leadership evolved towards being more strategic and less tactical, rather than something like "how do I get a license for Figma," that was another marker of progress of early adoption and success.
The front door analogy
Expedia equated their experience with Glean to a ‘front door’ analogy. The front door doesn't mean everyone has to walk through it: deliveries still go through the loading dock, and someone picking up a paycheck isn't going to use the delivery entrance. In a mall, you don't park at one end of the building if the store you need is at the other end. There isn't a single door for every purpose, but there needs to be a way to guide people to the right place.
Glean, in that framing, is one of Expedia's primary front doors, not because it's the only tool, but because it connects enterprise context without forcing people through a single, rigid path once they're in. Glean's MCP support makes that flexibility a reality in practice: someone can enter through Glean and still reach the surface they actually need to work in.
Expedia currently maintains roughly six AI tools, including SaaS-embedded assistants like Rovo and Slack AI, as well as frontier models and Glean. The team isn't trying to shut any of those doors, since builders who are comfortable working in a particular model or tool should be able to keep doing so. Where Expedia does actively consolidate is when there's true duplication: two tools solving the exact same problem is an unnecessary decision to force on users. Elsewhere, the team is deliberately not turning on universal enterprise search within tools like Atlassian and Slack—they want broader, context-dependent enterprise questions to be guided toward Glean instead.
Letting practitioners design the workflow
One of the clearest lessons from Expedia's rollout: watch what people actually build, rather than prescribing it for them. They described trying to pitch Glean to a team as a way to summarize their quarterly business reviews and pull action items from the transcript. That team ended up building a complete replacement for the QBR itself, in which all the information that normally would have gone into a deck now lives in Glean. Users can query that pool of information directly before the meeting, which is then spent discussing open questions rather than sitting through a presentation.
Expedia also approaches enterprise AI as a collaborator rather than as a static tool. When an AI response doesn't land, the guidance is to treat it like a person: give it feedback about what was wrong, and try again, rather than abandoning the tool after one disappointing result. Employees are also encouraged to think of themselves as orchestrators, not just as the ones doing the task.
What's next in Expedia’s AI journey
Trust is key to the continuation of Expedia’s AI transformation. They’re also looking for more personalization in AI, a "digital co-worker" that proactively helps rather than waits to be asked, and knowing where a human still needs to be in the loop. On the more operational side, Expedia is looking to connect more applications and tools to Glean.
Expedia's story is a reminder that a front-door strategy is about building trust—no matter which door someone walks through, they end up exactly where they need to be thanks to Glean.
