
Five Tensions in the Room
Everyone in this room has a strategy for AI. Whether it’s working is another issue.
The conversations happening at this summit go beyond adoption. They will address what happens when ambition meets reality, when speed collides with trust, and when the channels you’ve built your business on start to shift beneath you.
The gap between AI strategy and AI reality is wide; most organizations are further along on the slide deck than they are in production. The distance between the two is where the real decisions live.
The five tensions below are where that gap is widest. Each one corresponds to at least one session on today’s stage, each includes data that should make you uncomfortable, and each comes with a question worth putting directly to the speaker.
These tensions don’t have easy answers, but the leaders who navigate them best aren’t waiting for certainty. They’re building the judgment to act decisively without it. That’s what today is for.
— Rafat Ali, CEO & Founder, Skift
How the Day Is Designed
Each session at the Skift Data + AI Summit is built around a specific decision, not a topic. The moderator’s job is not to introduce a speaker, but to name the tension the audience is facing, drawing out the unique intelligence held by that speaker and synthesizing its meaning.
The day runs in three acts:
Build the Stack
What does production-grade AI require, and are you building on infrastructure that will hold?
Run the Business
What breaks when a pilot meets a real organization, and who owns the transition?
Drive the P&L
Where does AI show up in revenue and cost, and can you tell the difference?
The five tensions below thread through all three. You will hear the same underlying questions (pilots vs. production, speed vs. trust, build vs. buy) answered differently by operators at different stages, with different bets. That friction is intentional. The goal is to correct assumptions and adjust expectations, rather than to reach a consensus.
Agenda
Agenda subject to change. See the latest agenda for the most current version.
The Five Tensions
Pilots vs. Production
That ratio belongs to Carnival Cruise Line and it is not unusual. MIT found that 95% of organizations report zero ROI on generative AI projects.
The skills that get you to a pilot (curiosity, speed, low governance) are often not the ones needed to get to production. The result? Most travel organizations haven’t meaningfully scaled AI yet. Skift Research found that fewer than one-quarter of companies in the industry say they’ve scaled generative AI and are using it widely, and only 2% say the same about agentic AI. The organizations that crack this first will have an advantage that compounds over time and leaves others in their wake.
The decisions you’re likely making right now
- Should we consolidate our AI pilots into a single, scaled program, or keep running parallel experiments until one clearly wins?
- Should we hire for AI execution or continue relying on the team that got us to the pilot stage?
- Who in the organization owns the transition from experiment to operating function?
In the room
- Ask Expedia’s Shilpa Ranganathan how to decide which of 1,500 employee-built agents actually makes it to production.
- Ask IHG’s Wei Manfredi what breaks when a pilot hits real hotel operations.
- Ask Amex GBT’s John Sturino who owns the outcome when responsibility is distributed too broadly.
Speed vs. Trust
AI in pricing, customer service, and personalization runs on traveler trust. But even millennials and Gen Z, who are more likely to embrace AI than older travelers, aren’t giving that trust to companies yet. Part of this is because the pressure to move fast creates visible governance gaps that erode credibility.
This is already playing out in practice. Teams are pulling back, adding human oversight, and rethinking what “ready” actually means when speed and trust pull in opposite directions.
The decisions you’re likely making right now
- Where do we draw the line between AI autonomy and human oversight, and who in the organization owns that decision?
- How transparent do we need to be with customers about where AI is making decisions on their behalf?
- How do we ensure our brand is accurately represented in AI-powered search and booking tools that we don’t control?
In the room
- Ask Sierra’s Pol Peiffer what breaks when nobody inside the travel company is responsible for managing the human/agent interaction.
- Ask Booking.com’s Vipul Hingne how to build at scale when research shows only 6% of travelers fully trust AI — and the agent has saved 150,000 developer hours on the inside, but consumers still won’t let it decide for them.
Restructuring vs. Readiness
The travel industry is reorganizing work around AI faster than it is preparing people for it. BCG and NYU found that only 2.9% of travel workers have AI skills, the widest gap of any major industry, while 36% of hotel and airline employees report receiving no formal AI training at all. AI upskilling has taken hold at a handful of travel companies and several have noted that where it’s working with teams, it required deliberate change management investments most organizations haven’t made. We are finding that AI adoption looks less like a technology rollout and more like an organizational transformation.
At the same time, CFOs are cutting headcount and citing AI on earnings calls, seeking proof in the margins. As roles are redeployed and workflows redesigned, the human element of change management threatens to undermine any meaningful acceleration of AI.
The decisions you’re likely making right now
- Who in our organization owns the transition to AI adoption for non-technical employees?
- How do we enable AI for a workforce that is overwhelmingly frontline and hourly, and never opens a laptop?
- How can we best offer reskilling and education opportunities without destroying workforce trust?
In the room
- Ask Hilton’s Michael Leidinger what AI enablement looks like for a workforce that is mostly on its feet, not at a desk.
- Ask Marriott’s Colin Coleman what the AI Community of Practice actually does.
- Ask Amadeus’ Gaëlle Bristiel what it actually takes to move an engineering workforce from AI adoption to AI fluency.
- Ask Air Canada’s Firas Al Osman what it actually means to design an AI and digital strategy from scratch when you are the first CDO a major airline has ever had – and which legacy assumptions are the hardest to discard.
Build vs. Buy
The build vs. buy decision looks different depending on where you sit. For a platform operating at global scale, owning more of the stack can mean better margins, clearer differentiation, and greater flexibility. For others, it can mean distraction, debt, and delay.
One question that most companies have not yet answered is which capabilities are genuinely differentiating, and which are effectively commodity.
Where a company sits on the AI maturity curve often determines the right answer, but the curve keeps moving. The leaders in this room have made different bets and today is a chance to stress-test them against each other.
The decisions you’re likely making right now
- Which AI capabilities are genuinely differentiating for our business rather than commodity functions we should buy?
- How much vendor dependency are we willing to accept, and what’s our exit strategy if a key AI partner pivots or fails?
- Do we have the internal talent to build and maintain proprietary AI systems, or are we underestimating what that actually requires?
In the room
- Ask Mews’ Richard Valtr where the line is between what’s worth owning and what isn’t.
- Ask TUI’s Jie Zheng what happened to adoption after the initial push, and whether course access and capability building are the same thing.
Control vs. Visibility
Travel brands have spent years optimizing the direct booking experience, but AI is changing the calculus entirely. AI doesn’t send travelers to your website to browse and compare. It returns a shortlist based on what it can find, parse, and trust about you. If your data aren’t structured to speak to AI systems, you may not make that list at all. The new shelf space isn’t search rankings or OTA placement, it’s whether AI can read you clearly enough to recommend you.
That makes this perhaps the sharpest tension of the five: expose your data and restructure your operations to capture AI-driven traffic, or protect the first-party booking funnel you’ve built and risk becoming invisible. The industry is moving from search/scroll/compare to ask/shortlist/decide.
The decisions you’re likely making right now
- Should we restructure our data and content to be more legible to AI systems, knowing it may reduce our control over how our brand is represented?
- Should we invest in optimizing for AI discovery now or protect the direct funnel we’ve already built and wait to see how the landscape settles?
- How do we measure brand health when AI is making the shortlist decision before a traveler ever visits our site?
In the room
- Ask Evolve’s Arun Nagarajan how AI-powered discovery is changing the distribution calculus for vacation rentals, and whether structuring data for AI legibility is a competitive bet or a brand risk.
- Ask Cloudbeds’ Adam Harris what happens to the smallest operators when AI makes the shortlist decision and their data aren’t structured to be read.
What You Will Leave With
Are you building, reorganizing, or renaming?
The say–do gap in travel AI is real, and it is widening. A handful of companies are genuinely building at the model and orchestration layers. Most are somewhere between reorganizing and renaming; many don’t know which category they’re in.
By the end of the day, you should.
Not because the speakers will hand you a roadmap (they won’t). But because hearing how Expedia decides which of their 1,500 AI agents actually gets deployed, how Booking.com manages the trust problem when only 6% of travelers will let AI act for them, and how Marriott and Google Cloud assess what production-grade infrastructure actually requires — that evidence, in sequence, across one day, creates something a report cannot: the judgment to know where your organization stands and what the next decision needs to be.
You came in knowing that five tensions exist. Leave knowing which one is yours to resolve first.
