AI Questions Every Hotelier Should Be Asking

At The Hospitality Show (in Miami Beach, November 2-4), the AI conversation was everywhere, from the sessions on the Visionary Stage to the booths in the expo hall and in nearly every conversation at the Miami Nights reception. Most often, I heard questions, uncertainty, and a need for expert guidance: How will AI change the way guests find and book hotels? Who ends up owning the guest relationship? What is the return on all this investment?

Tuesday morning’s session “AI as Change Agent: What's Next for Travel and Hospitality” took a mighty swing at providing answers — and, as most such conversations do, raised even more questions.

The session was moderated by PwC's Jeanelle Johnson, Managing Partner and Travel Lead Client Partner, with panelists Benu Aggarwal, Founder and President of Milestone; Peter Chambers, Executive Vice President and Chief Information Officer of Montage International; and Priya Chandnani, EVP of Commercial Strategy at Sage Hospitality Group.

Chambers said Montage wants AI for speed and scale, not as a replacement for people. In his view, AI optimization is essential for getting a hotel discovered, and it can also help a hotel understand how a guest's stay went. Aggarwal added that AI helps hotels understand what a guest expects.

Distribution came up again and again. Aggarwal expects more and more bookings to come through OTAs, but said hotels that build a relationship with the guest can still own the direct relationship.

Chandnani separated the transaction from the stay: whoever handles the booking gets the data, but the hotel owns the stay and the communication around it, and that's what builds the relationship. Chambers saw both opportunity and risk: AI could be the industry's greatest opportunity, he said, but it could also open the door to entirely new businesses that step in between hotels and their guests.

Aggarwal said the first thing to fix is data consistency, so that hotels can be found by large language models. She described one project in which Milestone took every piece of data a brand had collected over years and built a new layer to understand and optimize it.

Being found also takes a story. Chambers said every hotel has a story to tell beyond its room rate, and that story will drive more AI discovery. Chandnani suggested letting guests book experiences, not just rooms, and curating those offers, a spa getaway, for example.

The onstage conversation mirrored what many hotel companies are encountering. The pressure to adopt AI is real, but they want proof that it's paying off, and the metrics for measuring it are still being built.

AI on the Expo Floor

Following up on the questions raised in the onstage discussion, I explored exhibitors’ AI offerings. A few highlights are illuminating:

Agilysys has built its AI strategy, called guestsense.ai, around embedding AI into core hospitality systems rather than selling it as a separate add-on. The company has introduced more than 30 AI-powered features and modules organized around four pillars: multi-modal user experiences, hyper-personalization, agentic process automation and revenue intelligence. That includes AI-native features in Agilysys PMS and AI enhancements across products such as Book, InfoGenesis POS and Eatec. Two more modules are in development: Revenue Intelligence and a next-generation central reservations system.

Oracle Hospitality is building AI directly into the property management system that many hotels already run on. It has launched Oracle OPERA Cloud Assistant, a set of AI capabilities embedded in OPERA Cloud's front desk, revenue management and configuration workflows. It includes AI-assisted room assignments, AI-generated rate descriptions, multilingual translation, and plain-language answers to staff questions about operations. Oracle made these features available worldwide to OPERA Cloud customers at no additional cost, which changes the ROI math for those properties. Wyndham, which runs more than 2,100 properties on OPERA Cloud, is among the brands putting the assistant to work. Oracle also offers AI Agent Studio for building agents around industry workflows. While Oracle has already built about 50 agents, it has acknowledged that many hotels still lack a clear idea of which agents they want.

Canary Technologies has built its guest management platform around AI. It includes AI guest messaging, AI Voice for calls, and upselling tools. Its biggest deployment is with Wyndham. In December 2025, after a pilot at more than 700 hotels, the two companies announced a global rollout of Canary's AI Voice, which answers calls, handles booking support and responds to guest questions. The ROI case is straightforward: industry data shows hotels miss up to 30% of inbound calls, and about a third of those calls are booking attempts. Canary has launched Hospitality AI Agent Studio, which lets hotels build, customize and deploy their own AI agents. The company has also launched an Agentic Sales Coordinator that handles group and event sales leads from first inquiry to confirmed booking.

Cloudbeds runs its platform on Signals, which the company calls hospitality's first foundation AI model. Signals uses causal AI, which models cause and effect rather than simple correlation, to power forecasting, pricing and guest marketing. Cloudbeds has introduced Ask Signals, a conversational interface that lets front desk teams, revenue managers and GMs ask questions of their operational, guest and revenue data in plain language. Ask Signals is currently in an early pilot program.

Hapi works one layer down, on data. It connects hotels, hotel companies and technology providers and moves data between their systems in real time, consolidating it into a single hospitality data model. Hapi presents that consistent data as the foundation hotels need before AI can succeed, which echoes Aggarwal's point on the panel. Hapi has hired a chief product officer with a background in AI platforms to help turn that connected data into real-time insights.

Each conversation came back to the same point: AI tools are arriving quickly, and hotel tech leaders need to know enough to judge what each one actually delivers.

5 AI Questions Hoteliers Must Ask

Based on my conversations on the expo floor, I suggest hoteliers ask these five questions in pursuit of real AI ROI.

1. What business problem does this solve, and how will we measure it? Before signing on, set a baseline and agree on the metrics that will show whether the tool is paying off. That might be labor hours saved, direct bookings won, upsell revenue or response times.

2. Is our data ready? Every AI tool depends on the data it's fed. Find out which systems the tool draws from, whether your data is consistent across properties and platforms, and what cleanup or integration work you'll need before you see results.

3. Who owns the data, and who owns what the AI produces? Ask whether your guest and operational data will be used to train the vendor's models, who owns the content and insights the AI generates, and what happens to your data if you end the contract.

4. What new security and privacy risks are we taking on? AI tools often need broad access to guest data and core systems. Ask how that data is protected, where it's stored, how access is controlled, and how the vendor handles a breach or an AI error that reaches a guest.

5. Who is accountable when the AI gets it wrong? Good governance means knowing where people stay in the loop, who reviews what the AI does, and which internal policies apply to its use. It also means your team has to understand AI well enough to oversee it.

Join the Conversation at HFTP's Hospitality AI Exchange

HFTP's Hospitality AI Exchange takes place February 2–3, 2027, in the greater Dallas area. It's a new two-day event developed by HFTP's AI Collective. The program covers how AI is changing hospitality operations, finance and technology, along with governance, intellectual property, security risk and practical adoption. For details and registration, please visit https://www.hftp.org/news/hftp-announces-brand-new-event-for-february-2027-hospitality-ai-exchange