February 13, 2025

CPS

Travel Adventure

Fail Fast, Succeed Sooner: Inside Booking.com’s experimentation strategy with Adrienne Enggist

Fail Fast, Succeed Sooner: Inside Booking.com’s experimentation strategy with Adrienne Enggist

Fail Fast, Succeed Sooner: Inside Booking.com’s experimentation strategy with Adrienne Enggist

Imagine this: you’re digging in search of treasure, only to realise after hours of toil that the map you’ve been following is upside down. For Adrienne Enggist, Senior Director of Product – Customer Experience & Platforms at Booking.com, this “Indiana Jones moment” is a metaphor for innovation: the need to adapt swiftly when a hypothesis proves incorrect. “We need to have the agility to do rapid iteration on a hypothesis,” she explains. “Fail fast, fail often, and course correct when necessary—it’s about learning from everything we do.”

Enggist stopped by the WiT Studio recently to discuss the approach to experimentation within one of the largest travel companies in the world, as well as the need to always stay customer-centric in a tech-driven industry.

 


Watch full interview:


 

Enggist’s approach to innovation is rooted in embracing mistakes as part of the journey. “It’s okay to make mistakes in interpretation,” she says, emphasizing that the key lies in understanding what could go wrong, and iterating based on insights. Leveraging tools like large language models (LLMs) has amplified this process. “The ability to use something like ChatGPT to refine my thoughts ensures I’m clear about what I’m trying to test,” she shares, adding that such tools are invaluable for validating hypotheses before committing resources.

While innovation drives Booking.com’s product development, customer satisfaction remains at the epicenter of product design. That, and of course, empathy, as Enggist highlights. Enggist acknowledges the delicate balance required between experimentation and delivering seamless customer experiences. “One of the main questions I ask is, are we shipping our org charts? Can the customer feel that they just moved from one product team to another? They shouldn’t see it or feel it,” she insists.

To maintain this balance, Booking.com employs a process of experimentation and data analysis. “We do post-analysis of experiments and meta-analysis on both successes and failures,” Enggist explains. Combining quantitative metrics with qualitative customer feedback ensures a holistic view of how changes impact users. “It’s important not to isolate one or two data points but to understand the full picture of what we’re giving to customers,” she notes, stressing the importance of aligning back-end innovation with front-end reliability.

Reflecting on her career journey, Enggist highlights how technological advancements have revolutionised travel. From her early days working with Icelandair’s first online booking engine to her current role at Booking.com, the shift has been monumental. “Back then, losing a website for 20 minutes wasn’t catastrophic because call centers handled bookings. Today, the stakes are much higher,” she observes.

The future, Enggist believes, will further integrate old concepts with modern technology. “The idea of the travel agent never truly went away,” she says. Advanced models and local LLMs are set to transform how travel is personalized and supported. “Imagine an agent that predicts issues like weather disruptions and reroutes your flights before problems arise. That’s an old concept making a big comeback,” she adds, painting a vision of a self-healing trip powered by AI.

At its core, Enggist philosophy remains deeply human. Her diverse background in hospitality and technology shaped her belief in creating meaningful connections. “I always look for the no-regrets moves that allow us to move forward,” she says.

 

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