The race has been heating up among business travel services looking to serve unmanaged or lightly managed travelers from small- to medium-size businesses.

Upside has been perhaps the most visible as a result of a concerted marketing campaign in print, radio, and TV appearances by founder Jay Walker. Now, a partnership with one of the biggest media companies in the world will further extend Upside’s exposure to business travelers.

The Wall Street Journal Business Travel Service, which is co-branded with Upside, allows users to book flights, hotels, rental cars, and Uber rides through its online booking site. The transactions, and subsequent service, are all provided by Upside. Users can connect by phone to customer service representatives 24/7 and the site has a chat service, as well.

The Wall Street Journal booking site, which was live over the weekend and has much of the look and feel of Upside’s own website, doesn’t tout gift card rewards or free headphones like Upside’s own website, but customers will receive them for applicable bookings.

Subscribers to The Wall Street Journal will also receive additional perks and deals through its WSJ+ loyalty program, but the service isn’t limited to subscribers only, and it isn’t behind a paywall like The Wall Street Journal news site.

“Basically, The Wall Street Journal is being an online travel agency, we’re just enabling it,” said Walker. “If you buy with them, we have a common infrastructure. We’ll know exactly who you are. What’s nice here is once you’re a Journal user, you might change jobs or do something new; you don’t have to start over, [because] we know who you are, we know what you like, and we actually care about you.”

Users will be able to access their itineraries and receive service across the Upside site, app, and Wall Street Journal booking site. Upside released a mobile app for the first time last week, enabling chat-based service inside the app similar to that provided by its competitor Lola.

Walker took out several full-page print ads in the newspaper this year, and the move seems to have paid off. Upside is looking to explore more partnerships.

It seems like teaming up with high-profile brands could be a more efficient way of reaching high-yielding business travelers than traditional advertising for the little-known Upside brand. The disadvantages are Upside has to share revenue with partners and doesn’t get the brand punch that would come with winning customers on its own.

What’s in It for The Wall Street Journal?

The Wall Street Journal views the tie-up as a value-add for its WSJ+ program, and the goal is that the partnership will generate revenue for the company.

The Wall Street Journal plans on putting some marketing muscle behind the new booking site across the Dow Jones network of sites.

“We’ve begun to expand into thinking more about memberships and what additional tools and services we can build out,” said Suzi Watford, chief marketing officer of Dow Jones- Wall Street Journal. “We also make sure we understand our customers. We have a very large professional audience and we want to make sure were building things that are relevant to our customers… we’re moving from a transactional relationship to a membership relationship. The opportunity to join forces [with Upside] and solve the customer problem makes sense.”

The BCD Travel Connection

A big piece of the deal is based on Upside’s relationship with BCD Travel, which provides the customer service solutions for the new site. BCD Travel is also a major investor in Upside.

The history of online travel is fraught with cautionary tales of media companies trying to push into online travel booking and struggling with it.

The New York Times partnered with Trip.com in the early 2000s to enable online bookings through its travel section online, and nothing much came of it. USA Today has experimented for years with various travel brands catering to both consumers and travel agents.

There are countless other media examples with varying success, but none have been wildly successful. These efforts, however, have been mainly geared toward leisure travelers, who are less likely to become repeat customers.

“Unmanaged business travel is the last great sector that nobody really addresses or provides serious value or service,” said Walker.

“The Soviet era in business travel,” he said, meaning the top-down dynamic in much of managed travel, “is going to end for customers as the age of the fully empowered digital traveler comes. Mobile, big data, chat, and artificial intelligence are going to completely revolutionize [business travel].”

For now, Upside is hoping the allure of free headphones and always-on customer service keep customers coming back.

Photo Credit: The Wall Street Journal teamed with Upside to offer a booking site for business travelers. Pictured are travelers at an airport. Patrick T. Fallon / Bloomberg