From Ryokans to Ray Bans: Booking.com’s Adrienne Enggist on AI breaking barriers and a world without screens

When Adrienne Enggist walks into a room, whether it’s a tech summit in Amsterdam or a ryokan in Arima Onsen, she brings the future with her.

At WiT Japan & North Asia 2025, which wrapped up on Tuesday, Booking.com’s Senior Director of Product for Customer Experience and Platforms joined me on stage in Tokyo for a candid conversation that ranged from the promise of agentic AI to the very human importance of empathy in product design.

It was equal parts travel tech TED Talk, product masterclass, and gender equality manifesto, all filtered through the lens of someone navigating Booking.com’s transformation at hyperspeed.

From Autocomplete to Autonomous Colleague

We began with the AI acceleration that’s felt like “seven dog years in one human year.”

“In the last eight months, we’ve gone from autocomplete on steroids to autonomous digital colleagues,” said Enggist, describing the rise of agentic AI, systems that can set their own goals, break them down, use APIs, and execute tasks with minimal human intervention.

“AI can take on a goal or assign a goal to itself, break down the steps it needs to complete that goal, actually use tools. So think things like access to APIs and payment platforms and so forth, and then fully execute based on just a pure instruction set. It’s here.”

She painted a Venn diagram where productivity and customer experience overlap. “The real excitement happens in that 20% overlap, the same orchestration platform that drives internal productivity also accelerates customer features,” she explained. Booking.com’s product managers now prototype with UX using shared AI-driven tools, reducing weeks of work to mere days.

It’s AI with both a brain and a bedside manner.

An Aha Moment for Ryokan Owners in Arima

From the stage, Enggist transported us to a room full of 80 ryokan owners in Arima Onsen where she wanted to understand their experience of trying to get tourists away from the over-touristy golden route to places such as Arima, which are well-known to Japanese but not to foreigners.

“There are so many opportunities to improve the communication, first of all, between ryokan partners and ryokans to have that constant dialogue with guests before their stay – understanding dietary needs, understanding the type of experience the customer wants to have.

“Indeed, there’s a possibility for AI to become that communication point that can be done at scale to bring you more foreign visitors.”

During the meeting with the ryokans, she demonstrated a simple but powerful use of ChatGPT to translate a Japanese menu and recommend dishes based on her preferences.

“When I showed them how this could make their lives easier, I saw the moment the penny dropped,” she recalled. “It was an aha moment.”

For Enggist, this wasn’t a novelty. It was proof that AI can help scale cross-cultural communication and foster the kind of personalized experiences Booking.com wants to enable –especially in a country like Japan, where the tourism goal is to double international visitors by 2030 without degrading the experience for locals or travellers.

“It’s about intelligent discovery,” she said. “Helping people find the hidden gems and managing expectations before the journey even begins.”

From Keywords to Vibes: Meeting Intent Earlier

Enggist spoke about the evolution of travel inspiration – from Google keywords to TikTok vibes.

“Now, intent is expressed in videos, reels, voice, not just searches,” she said. “We’re working on parsing those 30-second inspirational videos into bookable itineraries. Imagine being able to watch a TikTok and get the whole trip laid out for you.”

That shift is powering a new age of semantic search and composable experiences. Booking.com is working on assembling dynamic interfaces that respond to real-time intent, all personalized, all adaptable.

“It’s no longer just personalisation. It’s adaptation,” she said, echoing Chris Hemmeter’s comments from WiT Africa. “We want the platform to understand user behaviour in the moment and respond accordingly.”

Is Booking.com keeping an eye on social commerce? Absolutely.

“Of course – social commerce, magical commerce, AI-generated commerce – they’re all coming,” she said. “Especially in Asia, where the lines between inspiration, conversation and conversion are blurring.”

Adrienne Enggist: “AI can take on a goal or assign a goal to itself, break down the steps it needs to complete that goal, actually use tools. So think things like access to APIs and payment platforms and so forth, and then fully execute based on just a pure instruction set. It’s here.”

Regulation: Hitting the EU High Water Mark and Scaling Globally

As we discussed EU regulations and their impact on global rollouts, and if that might slow down Booking in executing in growth markets like Asia, Enggist flipped the narrative.

“The interesting thing about regulation is that if we can hit the high water mark of EU regulation for data, privacy, digital market and digital services acquisition – if we can hit that regulatory high water mark – it means that we can open up, scalably, other markets much more easily.

“That is the mission we’re on right now – to create this gold standard and then immediately be able to run out scalable experimentation. So rather than trying to do market specific implementations, we’re first getting over this leap of hitting that EU standard, and if somebody becomes more restrictive than the EU, then we’ll meet that standard, and apply to global.”

Asked if that could be a disadvantage in slowing it down in execution in markets like Asia, she argued that “restraint can be a catalyst for innovation,” and emphasized building stable platforms with privacy, accessibility, and compliance by design.

“We’re aiming to hit the EU’s gold standard for data and compliance,” she said. “That way, we can scale globally with confidence.”

Empathy and The Gender Lens

And then came the empathy question and whether women bring a unique lens to travel tech. Enggist does not believe it’s necessarily gender specific but about lived experience and diverse teams, beyond gender.

“Diverse teams surface edge cases that may seem niche today but will become key differentiators tomorrow.”

But she didn’t let gender off the hook entirely.

To women, she offered this advice: “When you feel imposter syndrome, you’re actually in the zone of learning and growth. Get comfortable there – it means you’re getting better. Also, you don’t necessarily need to be from a technical background or push code. I didn’t push code into production until I was almost 30 years old, and then I only did it a couple of times, and then I moved in product management.”

And to men? “I wish that men would spend a little bit more time thinking about the fact that if we could do a bit more research, looking more into the advocacy side of things, we might be saving ourselves a lot of time, so maybe perhaps it’s better to go slow before.”

The Next Gen Travel App: Predictive and Preventive

Enggist envisions a travel future where the next big disruption isn’t just digital, it’s predictive.

When asked what the next gen travel app must have, Enggist without hesitation said, “We need to think about preventing disruption. This is something that we could call ‘Omotenashi’ for the digital age; taking extra care, predictable care of when things might go wrong, so that you can, beforehand, make sure that nothing could go wrong. Right now, we are good at fixing things reactively, but proactively predicting disruption and preventing it is going to be the next part.”

“We need a break from screens”

Enggist lit up when the conversation turned to wearables and ambient computing. With Booking.com already exploring screenless interactions, she dreams of a world where we’re not buried in our phones during a temple visit or concert.

She’s excited about the recent partnership between Apple’s Jony Ive and OpenAI’s Sam Altman to design a product for the future, as well as development of products such as the Ray-Ban Meta AI Glass.

“Having spent the last week touring around in Japan and with other tourists in tourist spots, the dependency on screens to do things is really, almost disruptive at this point. People walking around with their selfie sticks, holding their phones, either to read something or to just make a record of it. I think that we all need a little bit of a break from that.”

She imagines “a sort of ambience, no screen experience of AI embedded into our day to day life. I think it’s going to feel awkward or unusual at first, but then it will start to become so critical. I’m just really, really delighted about it.

“I want to get away from screens. I’m excited about a future where AI is just part of the environment – ambient, intuitive, natural,” she said. “We’re getting close.”