By Lukas I. Alpert 

When New York Times Co. launched its NYT Now mobile app last year, hopes were high internally that it would appeal to younger readers and ease them into the habit of paying for quality news.

But after a few months, it was clear that the subscription service, a cheaper and slimmed-down version of the main Times app, wasn't meeting expectations. In the end, only about 20,000 people agreed to pay $8 a month for it, well short of the newspaper's target of 200,000, said two people familiar with the matter. In May, 13 months after its launch, the Times made NYT Now free.

The change signaled a shift in digital strategy at the Times toward courting young readers with free content rather than trying to turn them into subscribers right away. That approach has the Times experimenting, to varying degrees, with making its content available across a multitude of platforms, from Facebook Inc.'s Instant Articles program to Apple Inc.'s coming News app to messaging platform WhatsApp and even on Starbucks Corp.'s mobile app.

The moves, however, leave the Times with a delicate balancing act: The paper is trying to boost its Web and mobile audience to bolster ad sales without undermining a steadily growing digital subscription business that has drawn almost one million customers and contributed 11% of the company's revenue last year. The newspaper's top digital executives argue that aggressively going after younger readers on platforms outside of the Times will persuade some to subscribe.

"We need to be wherever readers are, regardless of the platform," said Kinsey Wilson, the Times' editor for innovation and strategy, echoing sentiments often heard from executives at digital startups like BuzzFeed and Vox Media Inc. "We consider this to be a series of experiments to figure out what our audience wants and how best to make them paying customers."

The Times' digital approach has been more aggressive than many other large traditional publishers, like the Washington Post and Gannett Co.'s USA Today, which have so far stayed on the sidelines of Facebook's and Apple's news initiatives. The Wall Street Journal, owned by News Corp, said it has engaged in talks with Facebook and Apple but has yet to sign on to either program.

The new way of thinking has taken hold in the 16 months since the Times published an in-house study, the Innovation Report, detailing where the paper was failing to adjust to the fast-changing media landscape. Findings included the declining value of the home page, the publication's need to experiment more, a lack of digital talent, and a need for more collaboration between the newsroom and business side.

The Times is trying to address a problem faced by all traditional publishers, including The Wall Street Journal: Younger readers now get their news from a wider variety of nontraditional sources--and it is usually free. A recent Pew Research Center survey found that six out of 10 people between the ages of 18 and 34 said they got some political news on Facebook, compared with just 17% from the Times.

"We need to build habits to get people to come back to us every day," said Alex MacCallum, the paper's assistant managing editor for audience development.

In recent years, the Times, like other newspapers, has come to rely more heavily on circulation and subscription revenue to offset steady declines in print ad revenue. The Times' biggest move was erecting an online paywall in 2011 that generated $169 million last year. Thanks to online subscriptions and print edition rate increases, circulation overtook advertising as the biggest driver of revenue in 2012.

While print and digital circulation sales rose 22% from 2010 to 2014, ad revenue fell 15% to $662.3 million. Digital ad sales, while growing, totaled a modest $182 million in 2014 and haven't come close to offsetting the decline in print advertising. As a result, over the past five years, the company's overall revenue growth has been effectively flat, so a slowdown in new digital subscribers could prove destabilizing.

The shift away from print has meant falling ad revenue industrywide. Ad revenue at the Journal fell 11% in the quarter ended March 31, although its emphasis is increasingly on growing digital subscriptions. Gannett Co. just reported a 11.5% decline in second-quarter ad revenue. This has led all publishers to make digital strategy a priority in newsroom structure and hiring.

John Janedis, an analyst at Jefferies, predicts that growth in the Times' digital subscriber revenue will taper in the next five years. At the same time, print ad revenue is projected to continue falling faster than digital ad sales rise, which he estimates will reduce the Times' annual revenue by as much as $100 million by the end of the decade.

"The problem the Times has is that they have no more revenue streams to mine," said one former New York Times executive. "The real risk is that if you start making your content free elsewhere, it may end up giving no incentive to new readers to start paying, and that could cause a dangerous spiral as time goes on."

In recent years, the family controlled New York Times Co., which has a market value of $2.2 billion, has pared back its holdings, selling off the Boston Globe, About.com, TV and radio stations, and other assets. While that has allowed the company to bolster its balance sheet and focus on its flagship brand, it means it is largely dependent on its namesake publication's ability to evolve. Arthur Gregg Sulzberger, son of publisher and chairman Arthur Sulzberger Jr., and his cousin Sam Dolnick, have been instrumental in many of the Times' digital projects and last week both were promoted to senior newsroom positions.

Mr. Wilson, who joined the Times in February, said using the vast scale of social networks and outside distribution platforms is essential to connecting with new audiences.

For example, Facebook's Instant Articles allows publishers to publish free content directly on the social-media site rather than have it link back to the publication's site, something Facebook says will greatly speed load times on mobile. Apple's news app, meanwhile, will bundle free content from several outlets into a customizable stream.

"This is very different from going only after eyeballs and clicks. You have to deliver value and you have to help people navigate in a world where they are overwhelmed with information," Mr. Wilson said. "With that, we believe the economics will follow."

Mr. Wilson said the advertising split Facebook is offering--publishers keep 100% of any ads they sell and 70% if Facebook sells the ad--made the deal "mutually beneficial."

"The Silicon Valley approach is to learn and tweak what you did yesterday or last week and adjust," said Ms. MacCallum. "A newsroom in the new era requires that kind of constant strategic thinking."

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