This sponsored content was created in collaboration with a Skift partner.
A traveler lands in a new country and reaches for a phone. The boarding pass, hotel address, ride-hailing app, maps, payment tools, and messages all live there, and every one of them assumes a working connection.
Without a reliable connection, even routine parts of the journey can become challenging. A hotel may lose contact with an arriving guest, a ride-hailing service may be unable to connect a passenger with a driver, and an airline’s digital services may become inaccessible at a critical moment.
That was the central challenge that Richard Trinder, senior director of strategic partnerships at Holafly, an travel eSIM provider, discussed with Dan Marcec, intelligence editor at Skift, at Skift Global Forum 2026. No single travel company controls the entire journey, yet a connectivity failure can affect the experience travelers associate with every brand involved. For Trinder, addressing that vulnerability requires closer partnerships and making connectivity part of the travel experience from the outset.
The Trip Begins With a Connection
“The smartphone has increasingly become the control center of our lives,” Trinder said. It holds boarding passes, payment tools, maps, messages, and, increasingly, digital identity documents. When the phone cannot connect, much of the trip can become inaccessible at once. With a boarding pass on the phone, he said, losing connectivity is “a crisis.”
The growing dependence on smartphones has also changed travelers’ expectations. Trinder pointed out that consumers have spent decades getting accustomed to seamless, on-demand digital experiences. They now expect the same reliability when traveling, even as they move between countries, networks, and service providers.
Those transitions are particularly vulnerable. Trinder highlighted international border crossings, where changes in connectivity zones can interrupt service, and airport Wi-Fi, which can be patchy, insecure, and susceptible to cyberattacks. The consequences become more serious when travelers need to retrieve information or communicate during a disruption.
As Marcec pointed out, a hotel has no control over an airport’s connectivity failure, but it still faces the consequences when a guest cannot communicate with the hotel. Trinder warned that these breakdowns can affect customer satisfaction, brand perception, loyalty, and the likelihood of a repeat purchase.
“Today, the consumer has zero tolerance for friction,” he said.
Peace of Mind Without Thinking About Data
Marcec compared connectivity to basic hotel amenities like clean water and air conditioning: Travelers expect them to work and only notice when they don’t. Trinder agreed that connectivity has become a basic need, “just like the air we breathe and the water we drink.”
At Holafly, that thinking informs a company-wide emphasis on traveler peace of mind. He described it as providing travelers with a sense of confidence, security, and safety by anticipating connectivity issues before they arise.
The stakes can be personal as well as practical. Trinder described a business traveler facing a deadline or someone who needs to reach family with an urgent message. In either case, the inability to connect can turn an already stressful situation into something more serious.
His argument was that travel companies should make every effort to pre-empt these moments rather than leave customers to solve connectivity problems themselves. A relatively small part of the overall travel purchase can have a disproportionate effect on the experience when something goes wrong.
A Journey No Company Owns Alone
Delivering that peace of mind requires coordination across companies that may otherwise have little to do with one another. Airlines, hotels, booking platforms, and connectivity providers each control different parts of the experience, while travelers increasingly expect those services to work together.
Marcec connected the discussion to a broader theme at Skift Global Forum: Travel companies, including Uber and Airbnb, are looking for ways to take greater ownership of the customer experience. But even as companies expand their reach, they remain dependent on services outside their control.
“No one travel provider or travel company in this room owns the journey end-to-end completely,” Trinder said. “We have to partner up.”
For Holafly, that means changing how connectivity is sold and delivered. Rather than treating an eSIM as a separate purchase, Trinder wants travel brands to incorporate connectivity directly into their booking processes and digital services.
“We’re trying to move away from a reseller or vendor mentality and absolutely integrate it into the buying flow of how a journey happens,” he said.
Through application programming interfaces and software development kits, connectivity can sit within a partner’s app and purchasing flow rather than appearing as a separate product later. The case for doing so is practical: brands have already invested in their apps, and they don’t get the full value from them when a connection breaks.
Trinder pointed to maritime travel as one opportunity for this approach. Passengers at sea can move between connectivity zones or experience service blackouts, creating challenges that a travel provider may struggle to address alone. With coverage across more than 200 destinations, Holafly sees opportunities to work with global travel companies to reduce those interruptions.
But Trinder emphasized that technical integration alone will not solve the problem. He pointed to joint business plans as a way for companies to agree on shared objectives, responsibilities, and measures of success. Those measures can include ancillary revenue and other economic benefits alongside improvements to the traveler experience.
He also returned to a theme raised elsewhere at the forum: the importance of human intelligence as companies adopt more sophisticated technology.
“We need humans to talk to each other in companies,” Trinder said. Partnerships can take multiple forms, and coordinating them requires people to work through the behind-the-scenes complexity so travelers don’t have to.
Always On as a Safety Net
The importance of maintaining access becomes particularly clear when a trip does not go according to plan. A delayed connection, unexpected layover, or disruption caused by severe weather or geopolitical events can leave travelers needing information and assistance at precisely the moment their connectivity is most vulnerable.
Trinder offered Holafly’s Always On as an example of how connectivity providers can help address that problem. He described the product as a foundational layer of data that remains available for emergencies, with a particular focus on business travelers.
The idea is to ensure that travelers retain enough connectivity to handle essential tasks when their plans change unexpectedly. As Trinder explained, the value lies in knowing that a traveler can still access data when something goes wrong, without having to address a new connectivity problem in the middle of a disruption.
“Always On will give you that peace of mind that you’re okay,” he said. “You can do the emergency things you need to do.”
What Comes Next
The conversation also raised a longer-term question: What happens as travel companies build more of the customer experience around AI-powered services?
Marcec pointed out that the industry is investing in agentic AI and digital customer service, but those tools still depend on travelers being connected. Without reliable access, even the most sophisticated digital services may be unavailable when customers need them.
Trinder argued that companies should prepare by integrating connectivity into their existing services and purchasing flows now. While the implications of agentic AI are still taking shape, he sees application programming interfaces and software development kits as a foundation that will allow brands to adapt as the technology evolves.
“If you’ve got the plumbing and the integration there,” he said, rather than treating connectivity as an afterthought, travel companies will be better positioned to take advantage of AI.
Trinder expects eSIM connectivity to become as routine as contactless payments and digital boarding passes in about two years. Not long ago, neither was universal, he said, and now travelers tap and go without thinking about the heavy technical lift behind it. Holafly plans to build on that foundation. “We think of ourselves as being the travel companion of the future,” he said.
That ambition extends to additional services built on top of connectivity, with the goal of giving travelers the information they need at the right moment. But Trinder’s immediate message to travel brands was more practical: Identify where connectivity affects the customer experience, find partners that can address those gaps, and establish shared measures of success.
The technology may become increasingly sophisticated, but the desired result is straightforward. As Trinder put it, the question is: “How do we make it easy and peaceful for you?”
To learn more about Holafly, visit esim.holafly.com.
This content was created collaboratively by Holafly and Skift Studio.