Mr. Dadich

Not long after Scott Dadich was appointed executive editor of digital magazine development for all of Condé Nast, “the tops of the mastheads,” as the senior editorial staffs are called, filed into the company’s fourth-floor lecture hall for a series of meetings. Condé’s new iPad king was holding court.

This wasn’t the first time the tastemakers of 4 Times Square had met Mr. Dadich. He’d been shopping “that Wired thing” around the company since it debuted in iTunes’ App Store in May 2010 to considerable fanfare and a flurry of downloads.

But this time, Mr. Dadich faced a few more sets of crossed arms.

Mr. Dadich’s coronation, in August 2010, had come with a big window office on the seventh floor and a mandate to lead the brands that Si Newhouse built into the brave new world of the tablet, a device so shiny and elegant it made Condé’s stable of glossies look dull by comparison. Not surprisingly, Mr. Dadich’s arrival also brought a share of resentment his way in no small part because, even in the pages of this paper, his ascent from Wired, where he had spun a lagging title into ASME gold as creative director, was presented in near-messianic terms.

In a profile of Mr. Dadich in The Observer last August, Evan Smith, his former boss at Texas Monthly, likened Mr. Dadich to a “combination of Jesus and Pelé” before deciding, a moment later, that a comparison to Miles Davis and Frank Lloyd Wright was more apt. Legendary Esquire art director George Lois was, if possible, even more effusive about Condé’s new It Boy, declaring, “With a talent like Scott, magazines will never die.”

Within 4 Times Square, such praise was met with a degree of skepticism, but the breathless optimism among the Condé kingmakers who backed Mr. Dadich was to be expected. It’s hard to find a print dinosaur that doesn’t drool a little, post-recession, over the possibility of wading into a teeming new revenue stream. But Condé Nast felt the pressure more acutely than most. Mr. Newhouse’s puritanical if lavish stewardship of his beloved titles had left the company playing a careful game of wait-and-see through roughly the first three-quarters of the Internet revolution.

Condé’s initial flirtations with the web had been coy and tentative. Rather than sully established titles like Gourmet and Vogue, the company launched new sites, including Epicurious.com and Style.com, as a way of protecting its spoiled progeny from the rough-and-tumble Internet.

While Condé Nast was far from the only media company to find its established business model upended by the web, it appeared to be more paralyzed than most by the shift, perhaps because, in some ways, the rules of online media ran counter to the entire culture of the company. Where Condé Nast had been built on the notion of exclusivity—the idea that its gatekeepers held the keys to a sort of private club, doling out access to readers one glamorous photo spread or finely-turned phrase at a time—the Internet was messy, democratic and fundamentally untamable. Marquee titles like Vanity Fair, Vogue and the New Yorker seemed obsessed with hierarchies. The web obliterated them. Mr. Newhouse’s painstakingly constructed and assiduously policed royal court had come under threat—the villagers were massing at the gates!—and the ambivalence within the company was apparent: every attempt to welcome in the hoi polloi was met with an opposing impulse to head for higher ground on the castle wall.

Former web editors are still baffled by budgets that allowed for a suite to cover the Oscar party at Morton’s but can’t seem to assign to an extra desk for an online editor. Permission was required from the tech side before any print content was posted online. Nine months could crawl by before a request for an RSS feed or comment system on a site made its way through the system. Up until a few years ago, editorial staffers were shackled to a bloated corporate content management system that “forces web editors to spend enormous amounts of time wrangling the system instead of creating content,” according to one insider.

When individual titles began make their own forays into the web, they did so gingerly, slapping up what seemed to be placeholder sites geared mostly to picking up subscriptions. Meanwhile, rivals were popping up everywhere. “The biggest shame was that Vogue wasn’t Net-a-porter,” a former Condé Nast print editor told The Observer. “That was the missed opportunity of the century.”

The iPad, then, promised more than just a do-over. It was a chance for redemption. See what we did there? We’re not extinct! And for all his technical wizardry, Steve Jobs seemed a worthy partner, with his refined aesthetic and affinity for gated communities not unlike the neighborhood Condé Nast had occupied for years. The iPad seemed to promise that, both financially and culturally, the company could resort to its comfy old habits and maybe still survive.

Condé Nast’s digital efforts have been restructured so many times, it’s hard to keep the chronology straight. But call it CondéNet or Condé Nast Digital—as the digital arm has been named at various times—in some ways, it’s the same as it ever was.

IN THE FOURTH FLOOR conference room, Mr. Dadich preached his new gospel with the relentless enthusiasm of a mystical prophet. His crystal ball was showing nothing but iPad. Sales projections for Apple’s magic screenwere thrown around with exuberance. Here’s what we’re doing. Here’s our future.

All that sounded promising enough. But there was a catch: there would be no dedicated hires. Instead, existing art and production staffers from the print side would be responsible for making two iPad layouts (one in portrait and one in landscape, per Mr. Dadich’s vision) on Adobe’s platform. The idea was that since Condé Nast used Adobe’s InDesign and InCopy software to create its magazines, sticking with Adobe would make repurposing content easier. Based in Silicon Valley, Adobe had seen where the business was heading and was building software to get into the tablet game. In fact, the first Wired app was built with a lot of Adobe manpower and then rebuilt when Apple banned the Flash system Adobe had been using from the iPad.

Despite the setbacks Wired had encountered, Mr. Dadich made it all sound simple. “What we’re going to do is have workflow specialists come in, so it’ll be actually less work,” a source recalls him saying.

“I think that’s a terrible idea,” says Khoi Vinh, former NYTimes.com design director and author of the highly regarded design blog Subtraction. (A sign of Mr. Vinh’s influence: he boasts 210,267 Twitter followers to Mr. Dadich’s 3,155.) Mr. Vinh is highly critical of Condé’s print-centric, “magazine replica” approach to the tablet. “It’s like going to a Broadway stage crew, who are very talented at what they’re doing, and saying, ‘Can you help us create the next summer movie blockbuster?’” he told The Observer, adding, “I think it’s a fundamental misunderstanding of the way design works.”

Wall Street Journal director of design technology Erin Sparling felt the same way about retasking print folks to design for the iPads simply because they had used Adobe programs before. “That’s crazy,” Mr. Sparling told The Observer. “The assumption that it’s the same thing, just with a different output, is absolutely wrong. Just tacking it onto employees’ responsibilities seems like a recipe for making all of those employees very sad.”

It’s certainly been a culture shock. Some sources say art departments at titles like Vanity Fair, Glamour, GQ and Allure have had to give up their coveted down weeks between issues—time they once spent visiting museums and dreaming up gorgeous new layouts—in favor of working late on weeknights and weekends to produce pages in Adobe. They’re worried that burnout will turn to a morale problem, if not the makings of a full-scale mutiny.

Two talented digital designers, Chris Gonzalez, director of mobile product management at Condé Nast, and Vince Holleran, who helped create the New Yorker’s iPad app, both recently departed for Gilt Groupe. Anton Ioukhnovets, a former GQ art director, left the magazine last September after seven years for reasons unrelated to the iPad. Nonetheless, he said, “I saw it coming, and I was not interested. I didn’t want to do two jobs for the for the price of one.” He called the iPad “the bane” of his former colleagues’ existence.

In a statement emailed to The Observer, Condé president Bob Sauerberg, said, “From the start, we recognized both the opportunities and the inherent challenges of a new technology and medium. We have been aggressive in our digital development and we know the path to success can be bumpy. We believe in the talents and of our editorial teams to create their own apps—entrusting the design to those who have built our magazines. We are gratified with the way consumers are responding and we are extremely proud of what our teams have accomplished.”

While Condé swells with pride, there’s another aspect of its iPad initiative that baffles outsiders. Why lock in a partnership with Adobe while the market is still shaking out? “You don’t do a biz dev deal to get on the iPad! You just do an app,” said a source familiar with Condé’s digital operations.

“We, like our colleagues across the industry, are collectively inventing a new medium,” Wired’s editor-in-chief Chris Anderson said in another statement emailed to The Observer. “This is an exciting opportunity and our designers both want and deserve to be part of it. Designers come to Wired to innovate; this has the potential to be the most innovative thing we’ve done.”

That said, the transition might be a more natural one for Wired and its gadget-fiend readers. The latest unaudited numbers from the Audit Bureau of Circulation show Wired’s digital downloads capping at an average of 27,369 per month for the six months ending this past December. (For context, its first iPad App got more than 100,000 that month.) GQ’s app has less than half of that, with an average of 12,377 per month for those same six months, and Vanity Fair clocked in at just 9,438. Glamour’s iPad app, which was released in August, had a mere 2,471  monthly average for downloads. Condé seems buoyant about new circulation numbers coming out in August, pointing out that The New Yorker was the top grossing app in the App Store for most of the week after introducing a subscription offer.

Meanwhile, the numbers for the Nook, which requires little more effort than uploading PDFs of pages, are surging, and in some cases surpassing iPad sales.

In addition to dipping a toe into the Nook, Condé Nast is sniffing around Hewlett-Packard’s tablet. In April, AdAge reported that it hit the brakes on plans to deliver iPad editions across all its titles, saying they now need justification before launching an iPad edition. But the rhetoric of redemption remains. In a recent interview for Nieman Journalism Labs, Mr. Dadich was still backing the iTunes newsstand and the “dedicated container” for content that an app provides on an iPad, “where covers are the primary means of purchase and browsing.” To which one commenter replied, “All I see when reading this is an entire organization screaming, ‘WE WANT IT TO BE THE EIGHTIES GODDAMMIT.’”

AFTER THE RUDE AWAKENING of the recession, Condé Nast faced a turning point. It was clear the old model—concentrating on publishing elegant and high-end content and assuming that advertisers would line up for pages—was failing. Mr. Newhouse, who is in his 80s and has never been much for innovation, began increasingly to take a back seat, sources say, leaving a something of a power vacuum at the top of the company.

During the McKinsey era, when the white-shoe consultancy was paid seven figures to help turn things around, Condé Nast’s then-CEO and president, Chuck Townsend, was ready to ask for help. He created a ideas box—grandly named “The Power of Suggestion”—and invited any Condé employee with an idea to benefit the company to submit it. The best idea would be selected once each quarter, and the employee would be awarded a $10,000 bonus. But why, some wondered, would anyone with a truly disruptive idea give it away for $10,000 when they could walk to the Flatiron and get half a million in funding?

Later that year, Mr. Townsend handed over the president’s role to Bob Sauerberg, former group president of consumer marketing. That left Mr. Townsend (an operations-side suit), Mr. Sauerberg (a consumer marketing guy steeped in the world of blow cards and direct mail) and editorial director Tom Wallace (former editor-in-chief of Condé Nast Traveler), as the decision-makers charged with leading Condé to its digital destiny.

Though all had mastered various ins and outs of the print magazine business, at least as it was practiced in the last century, none were digital natives, and the mobile world was even more foreign. “These are not guys with iPhones in their pockets checking-in on Foursquare,” noted one insider.

It wasn’t a surprise, then, that the young Mr Dadich was viewed as something of a savior. “You know what it’s like,” a former employee told The Observer, regarding Mr. Dadich. “You sit in a room, and you don’t know much about a subject, but some person is able to discourse in it. All of a sudden someone says, ‘Wow this guy must be incredible!’ They’re anointed as the new king.”

And minting stars is what Condé Nast has always done best—from promising young designers selected as Anna Wintour’s favorites and aggressively promoted in the pages of Vogue, to internal staffers who find themselves propelled up the masthead. It’s the same model Condé used to promote James Truman, known as the “prince of Condé Nast,” to become the company’s second-ever editorial director.

“But,” the source was quick to point out, “just as in every royal family, the king has a certain time when he’s being fawned over, and then there will be a moment when someone chops off his head.”

It doesn’t appear likely that Mr. Dadich is on his way to the guillotine. But there are certainly those ready to plot a coup. Condé Nast employees described Mr. Dadich as “Tom’s boy,” and wonder if Mr. Wallace, the company’s editorial director, hasn’t developed something of a “mancrush” on his young protege. Many of the sources who spoke to The Observer wondered why, in a city suddenly teeming with venture capitalists, entrepreneurs and coders, a print guy like Mr. Dadich was picked to lead the way in the first place. One told The Observer that, last year, even Adobe requested a different point person better versed in interactive design. But that didn’t stop Condé from flying Mr. Dadich, who didn’t respond directly to an interview request, to Moscow a few months ago to deliver his spiel to the company’s Russian titles.

One source we spoke to said Mr. Sauerberg was busily trying to counter Mr. Wallace’s unwavering faith in Mr. Dadich, a relationship backed by Mr. Townsend. Then again, we heard some staffers blame Mr. Sauerberg for the seemingly short-sighted decision to partner with Adobe, while others pinned it on Mr. Townsend. Whichever view is closer to the truth may be less meaningful, in the long run, than the impression of a company on the edge of obsolescence increasingly falling victim to finger-pointing and internal power struggles.

It is, according to a Wired designer speaking from the magazine's headquarters out in San Francisco, a “snake pit.”

Still, there are signs that things may be changing. A few weeks into Mr. Sauerberg’s tenure, he tapped an unglamorous outsider, Joe Simon, an Indian expat from Viacom, to be the company’s first-ever CTO. It was a move toward what one source called “the way every other sane company in the world works.”

Mr. Simon’s biggest challenge might be finding a way to move beyond the Adobe partnership and a mind-set that looks at the iPad and sees a newsstand, but with virtual stacks of print.

“It’s obvious it wasn’t going to work,” said Mr. Vinh, the former NYTimes.com design director. “It’s only if you’re under the spell of this very traditional print-centric bias that you would ever think that this would work. I don’t know who the executive was that said this is the way we’re going to approach it, but this is not a decision that I would put on my résumé.”

ntiku@observer.com