Dennis Schaal Archives

Dennis Schaal is Skift’s Founding Editor and Executive Editor. Dennis has been a reporter focusing on online travel and short-term rentals for more than two decades at Skift, Tnooz, USA Today, and Travel Weekly. He is well-known for tough one-on-one interviews on stage at Skift events, including with the CEOs and top execs of Expedia, Uber, Booking Holdings, Priceline, Kayak, Hopper, and more.

Online Travel

Full Video: Fintech Is Booking’s Quiet Powerhouse, and It’s Getting Smarter With AI

Booking.com wants to engineer a future where payments unlock the full travel journey. As AI and agentic systems loom, it is making the case that the its future lies in easing friction, striving to be hyper-local, with fintech as a foundation.

Dennis Schaal | 8 months ago

Two men sitting in yellow chairs on stage at Skift Global Forum East.

Online Travel

Booking’s Fintech Boss on the Strategic Importance of Its ‘Very Profitable’ Payments Biz

Saving a basis point or two per transaction in Booking.com's payments business can turn into a windfall of millions of dollars. That's an edge that Booking.com is leveraging in payments, which are also central to its connected trip strategy.

Dennis Schaal | 8 months ago

Steve Hafner, Kayak CEO at the Skift Global Forum in New York.

Online Travel

Kayak CEO on $457 Million Writedown: Google Squeezed the Travel Industry Again

Google has been downplaying free organic links for many years. In the past year, its AI Overviews and other ad formats have basically forced travel companies to spend more for traffic. Kayak isn't the only player feeling the squeeze.

Dennis Schaal | 8 months ago

Booking Holdings CEO Glenn Fogel at Skift Global Forum 2025.

Online Travel

Booking CEO on the ChatGPT-Hotel Risk: ‘An Overblown Threat’

Booking Holdings had a strong third quarter. CEO Glenn Fogel acknowledged these are early days for the artificial intelligence boom.

Dennis Schaal | 8 months ago

Hotels

Mews Acquires AI Firm to Simplify Data Usage for Hotels

One big challenge with AI and personalization is that companies don't know how to manage the troves of data they already possess. DataChat hopes to simplify that process.

Dennis Schaal | 8 months ago

Online Travel

Will Agentic AI Turn OTAs Into Passive Order Takers?

No one yet knows who will be the winners and losers in the agentic AI battle. Developments are happening too fast. But few would argue with the fact that the online travel agencies face a substantial disruption risk.

Dennis Schaal | 8 months ago

Travelers on a food tour in Reykjavik, Iceland in May 2023 that was booked through Viator.

Online Travel

Activist Investor Starboard Value Details How To Fix Tripadvisor

So far Starboard Value hasn't publicly called for any leadership changes at Tripadvisor, but the activist investor's views aren't exactly a ringing endorsement.

Dennis Schaal | 8 months ago

A Navan advertisement at Heathrow Airport

Business Travel

Navan’s Business Travel Customer List Includes OpenAI, Perplexity, and Anthropic: Scoop

Navan's landing of OpenAI, Perplexity and Anthropic as customers is a coup, and shows the company's offerings resonate in Silicon Valley. But Navan's revenue is also broad-based geographically.

Dennis Schaal | 8 months ago

Online Travel

Airbnb’s Brian Chesky: ChatGPT Can Distribute Travel, But Cutting Out OTAs Is ‘Very Difficult’

It's the existential issue the travel industry is debating: Will OpenAI and other platforms become travel booking sites? Brian Chesky doesn't think so.

Dennis Schaal | 8 months ago

Online Travel

Hostelworld to Acquire Local Events Aggregator to Build Out Social Network

Whether this acquisition will be a difference-maker for Hostelworld may depend on how well flea markets and arts festivals resonate with its youthful cohort of guests.

Dennis Schaal | 8 months ago