One viewer is standing in the checkout line at the supermarket, scrolling through Facebook. Another is about to get on a train, and pulling up a video on YouTube, while someone else is sitting on the couch with their laptop, ready to devote three hours to binging a show.

“When you’re making content, the storytelling style is different for whichever platform,” said Dawn Ostroff, president, Condé Nast Entertainment (CNE). Having an intimate understanding of how the audience interacts with each platform—both established and emerging—has been key to the company’s successful digital video strategy.

“The question is, as the business evolves and the viewer’s expectation evolves, how do you stay ahead of the curve?” asked Ostroff. “What works, and what doesn’t work, and for what reasons?”

Ostroff will address just that at PromaxBDA the Conference, where leading media companies and agencies gather for industry-leading insights, strategy, creativity and professional development. This year’s annual summit is taking place June 11-14 at the Midtown Hilton in New York City.

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“What we really want to talk about is just how there is a different way in which this generation, Gen Z and Millennials, really watch content, and how content is being made for them,” Ostroff said.

While subject matters remain relatively constant, formats are constantly shifting, and tapping into those changes is something CNE has embraced.

For instance, a murder mystery that would be 48 minutes on Dateline, CNE does in five minutes on Snapchat. And the video series 73 Questions turns the linear talk show format on its head by creating more of a one-on-one relationship with viewers. In it, celebrities answer rapid-fire questions directly into the camera, while giving a tour of their homes.

“There’s an intimacy and a familiarity that feels very different,” Ostroff said.

That concept is front and center of a digital video distribution expansion, revealed at Condé Nast’s upfront this month, which includes new over-the-top (OTT) offerings with dedicated channels for Wired, Bon Appétit and GQ available on AppleTV, Roku and Amazon Fire, as well as 60 new digital video pilots for the 2018-2019 season.

“We have been working for the past five years on making our brand really relevant for a young audience sitting on video platforms,” Ostroff said.

The new OTT distribution “is a way for us to expand that for our viewers,” with longer-form content that creates more of a “lean-back, living-room experience.”

“It’s really another platform where people will be able to get our content,” she said.

But, “not everything is going to work,” she acknowledges.

It’s a lesson she learned early on, when transitioning from her role as president of entertainment for The CW broadcast network to founding CNE in 2011 when Condé Nast decided to build a thriving digital video, film, and television business based on its iconic brands.

“We started this division under the guise of there are so many assets, and movies made based from the magazines,” Ostroff said. In pivoting from a publishing company to a media company, the film and television side of the equation was pretty clear, but digital video “was really a guessing game because the industry really hadn’t evolved.”

“Originally, we started off thinking you make content for television, but you make it shorter,” she said. “That was a recipe for failure … All the knowledge and assumptions we made walking in the door were totally wrong.”

But they were humble enough to admit it, and also learn from those early mistakes, essentially “building a bullet train while laying the tracks.”

“The whole key is being nimble, and being able to recognize when to make a change, and do it,” Ostroff said.

One benefit of working in a digital medium is the transparency of data, and the ability to combine analytics and creative to make decisions.

“You never know what’s going to work and what’s not. But the bets we take are much more informed than the bets we would take if I was running a linear channel,” she said.

Ostroff first recognized that audiences were migrating to digital platforms during her time at The CW when the network began streaming full episodes, and she realized the potential for what CNE was building.

“We didn’t know much about how the transformation would evolve,” she said. The rate of change has been much faster than she ever would have predicted, but the industry itself, and business models positioned around that change, are still in their infancy.

“We were starting this business at a time when we were in the first inning. And we’re only in the second inning now as the industry continues to transform,” she said.

And the third inning?

“For us, it’s about monetization and building a business that is profitable. What drives us really is not only revenue, but our ability to turn a profit,” she said.

But from a personal standpoint, and for anyone working in the world of entertainment, that success is driven by something more.

“You have to be able to really get into a part of the business you feel excited and passionate about,” she said. “Roll up your sleeves, learn as much as you can, and focus on the work.”

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