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

Expedia CFO: ‘We Radically Changed the Direction of the Company’

Expedia has been downsizing its workforce over the last year, and plowing some of the savings into machine learning and AI. It's a playbook that's taking place across industries.

Dennis Schaal | 3 months ago

Travel Technology

Amadeus Acquired SkyLink to Infuse Its Products With Conversational AI

Amadeus has always been out-front about the adoption of new technologies, and this acquisition will strengthen its position in conversational AI.

Dennis Schaal | 3 months ago

3 young people inside a home clutching one another and looking fearful in a humorous advertisement

Online Travel

Kayak’s New Ad Campaign Signals a Marketing Dilemma as AI Grabs Share

Booking Holdings sees AI as the future of travel. Its Kayak brand's marketing doesn't touch on AI, but is trying to convince Millennials it's OK to book on smartphones and to use Kayak to navigate social media distractions.

Dennis Schaal | 3 months ago

An EV charger shown at the Cambria Nashville Airport Choice Hotels International

Ground Transport

Airbnb Is Testing Airport Pickups. Are Flights Next?

Airbnb likely sees how flights are driving Booking Holdings' connected-trip vision. The timing is unclear, but it needs flights if it wants to be a true "travel concierge."

Dennis Schaal | 3 months ago

Online Travel

Wyndham and Marriott’s Agentic Plans Put Pressure on Booking. Are the Concerns Justified?

Booking Holdings could survive hotel chains switching allegiances to the LLMs. But how long would it take for independent hotels to likewise jump ship?

Dennis Schaal | 4 months ago

Online Travel

Tripadvisor CEO Issued Confidential Memo to Employees on ‘Challenging’ Month: Scoop

There are conflicting messages at Tripadvisor these days. Goldberg told employees that it "will take time" for its 3-month-old strategy revamp "to show up in the numbers." Meanwhile, activist investor Starboard Value argued "the time for incrementalism is over."

Dennis Schaal | 4 months ago

a man sitting on a yellow chair on a stage

Hotels

Booking CEO Touts Ties With Independent Hotels as Agentic AI and Airbnb Seek Gains

We sometimes think of independent hotels as relatively powerless given the strength of the OTAs and the big hotel chains. Will agentic AI turn the tables?

Dennis Schaal | 4 months ago

Airbnb guests standing and talking in a doorway of a home in Cape Town, South Africa.

Short-Term Rentals

Airbnb Tests Loyalty Benefits. Chesky Says Program ‘Could Be a Massive Accelerant’

In 2018, Airbnb had a "superguest" loyalty plan in the works to reward frequent guests with premium benefits, but it never came to be. Might the loyalty benefits being tested resurrect some of those plans?

Dennis Schaal | 4 months ago

Airbnb CEO Brian Chesky speaking on stage

Hotels

Airbnb’s Hotel Strategy Is Now ‘Much Bigger’

There is absolutely no doubt that eventually Airbnb will take on Booking.com head-on in homes and hotels. But then what will set the two rivals apart?

Dennis Schaal | 4 months ago

Online Travel

Tripadvisor Faces Shakeup as Activist Investor Starboard Seeks Control

Starboard Value will likely find plenty of support among Tripadvisor's long-suffering shareholders.

Dennis Schaal | 4 months ago