The key for a media company trying to reinvent itself during this digital era is to have a strategy. And, preferably, one that works. The problem is, nobody really knows which ones do.

But there are no lack of glittering lures. Companies like BuzzFeed and Vice have raised big money at enormous valuations by selling themselves as quasi-ad agencies happy to create original content for brands. There are also platforms aplenty, like Facebook and Snapchat, willing to host your content on their sites for a cut of the ad revenue.

This is the environment that confronts Paul Greenberg as he tries to turn around Nylon Media. Started 16 years ago as a music and pop culture magazine aimed at young women, Nylon has struggled with the transition to digital. Last year it was bought by a private equity firm, which later installed Mr. Greenberg as CEO. He’s a digital journeyman, having previously been CEO at CollegeHumor, an executive vice president at TV Guide and head of digital at Time Inc.’s Lifestyle Group.

For Nylon, he’s taken a look at the landscape of platforms, native ads, events, e-commerce and banner ads and tried to pull them all together. Call it the unified theory of everything in digital. Mostly though, he argues that the strategy comes down to Nylon’s voice and the ability to pitch itself to brands and readers as the best way to communicate with young, hip, female music lovers.

In a recent conversation with The Information, Mr. Greenberg discussed his native ad play for Nylon, why it make sense for Nylon’s editor-in-chief to head up its sponsored content and why he’s skeptical of the content creators that are singing the praises of Snapchat and its new Discover video feature.