Lining the walls of the Chicago Sun-Times newsroom are striking, historic black-and-white photos. There are shots of former mayors mingled with seedy politicians, notorious criminals, and Pulitzer-winning breaking news photography. They are reminders of the paper’s storied past juxtaposed with its rocky present.

When I left the Sun-Times in 2010 after working as a Web editor and sometime reporter, many had completely written off the organization. Layoffs, declining readership, and bankruptcy had pushed the paper to the brink. Depending on whom you might ask, the paper was hours from liquidation in October 2009.

The Sun-Times is certainly not alone as a struggling news organization. A few blocks east, the Chicago Tribune is still mired in a never-ending bankruptcy filing. The 175-year-old New Orleans Times Picayune is scaling back its print edition to three days a week. Outside of The New York Times and some other titans that made early commitments to digital delivery, there are few old media news organizations that are thriving in the new world.

Yet the Sun-Times, two ownership teams later, is still afloat. And recent shakeups in the newsroom indicate a commitment to remaining relevant in a rapidly shifting media landscape.

Specifically, the Sun-Times’ new editor-in-chief, Jim Kirk, told Time Out Chicago media blogger (and former Sun-Times columnist) Robert Feder: “We are a technology company that happens to publish a newspaper. We deliver content. And we will deliver content on many platforms and in ways that we haven’t yet fully considered.”

Many cynics said, “Welcome to the party.”

“There’s no question they’re late. Maybe too late,” Feder tells PR Daily. “One of the reasons I left the Sun-Times in 2008 was because I saw the world passing us by in terms of how people use media. It took me a year living in the ‘real world’—away from the paper—to understand how dire the situation truly was.

“The bankruptcy and cutbacks that followed only made matters worse. Now, finally, the transition to a digital culture seems to be under way in earnest. But there’s very little room for error, and they’ve only got one chance to get it right.”

During my tenure there, which overlapped with Feder’s final year or so, plenty of lip service was paid to being a “Web first” news organization, but the reality was very different. Sure, we published most stories on the Web before they appeared in print. But there was never a premium put on using emerging technologies to engage readers.

Along with Kirk’s hiring, Craig Newman was promoted to managing editor after serving as head of production. Newman, 41, has been with the Sun-Times since 2003. Newman was instrumental in creating a social media presence for the Sun-Times, which wasn’t part of his job description at the time. Now, he says it’s impossible to be a viable journalism brand without a commitment to social media.

I recently sat down with Newman to discuss the company’s future and its retooled approach. He says the change stems largely from the Sun-Times’ new ownership group, Wrapports. But our conversation quickly turned to social media and its role in bolstering readership for mainstream media.

“The marketplace for information and reporting and journalism has evolved so much in the last couple of years that we need to figure out how to make ourselves relevant where people live and consume content,” Newman says. “We have to find out where people are [consuming news] and go there.”

I couldn’t help but see parallels between the work I do in content marketing with various brands and what the Sun-Times is trying to accomplish in connecting with readers. We’re constantly trying to find a way to fit the right message with the right tool. In a news organization’s case, the “message” just happens to be reported facts.

Newman lays out the challenge: “How do we take tools that are continuing to emerge—Instagram, Pinterest, Tumblr, whatever—and figure out what makes sense for us as a content provider and what makes sense for the content consumers?”

Though he acknowledges that along with the media landscape’s evolution, the competition has also evolved. Think of your Facebook experience and where traditional media fit in. If your news feed is anything like mine, your average Sun-Times (or any media outlet’s) news story is competing with content from brands and updates from my friends.

“The walls [dividing journalism and marketing] don’t exist like they used to,” Newman says. “It’s not that we’re asking journalists to go out and sell ads, but we’re disseminating knowledge along the same tracks as marketing and PR efforts, because that’s what the consumers are telling us they want.

“It used to be our competition was the Chicago Tribune (and the [Tribune-owned] RedEye) and to a lesser extent TV and radio. But that was strictly speaking from a journalistic standpoint. Now, our competition is everything.”

So, how does a news organization compete with everything?

Reporters are now armed with smartphones, and all of them are encouraged (though not required) to be active on Twitter and in other social spaces. Newman says ideally all of the organization’s reporters and columnists would be active in whatever social space makes the most sense to them.

Federal courts reporter Natasha Korecki is a prime example of how this is working. She’s amassed a healthy following by live-tweeting some of the city’s most high-profile cases, including the Rod Blagojevich trial and sentencing.

Much of the Sun-Times’ success or failure rests with Kirk, who many—including Newman—believe is the man for the job. Kirk jumped to the Sun-Times in April from Crain’s Chicago Business, where he was instrumental in retooling its Web presence. He has also worked at the Chicago Tribune, Bloomberg News, Adweek, and the recently shuttered Chicago News Cooperative. He also served as a reporter at the Sun-Times from 1995 to 1997, when he was escorted out of the building after telling his supervisors he had accepted a job with the rival Tribune.

“Hiring Jim Kirk was a grand slam home run for Wrapports and [its chairman] Michael Ferro,” Feder says. “I can’t think of a smarter, more focused or more capable individual to lead the company’s digital transformation. He seems to have a clear view of what needs to be done while respecting the traditions of Chicago journalism he has known all his life. Still, the challenge is enormous, and his success is by no means assured.”

What’s certain is that nobody seems to be questioning the Sun-Times’ commitment to becoming a modern media company. But the coming months will reveal whether the commitment pays off, and we’ll see whether the Sun-Times will become a legitimate, profitable “technology company.”

“Legitimate? Yes,” Feder says. “Profitable? I couldn’t possibly predict. But remember—we’re talking about guys with very big egos and very deep pockets.”

Kevin Allen worked at the Chicago Sun-Times from 2007 to 2010.

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