Greg Clayman has spent the past decade trying to build digital on-ramps for traditional media companies including News Corp. and Viacom, with varying degrees of success.

Now he’s gone native: Clayman joined Vimeo, the IAC-owned Internet video site positioned as the antithesis of YouTube, as its g.m. of audience networks in October. He’s charged with convincing indie filmmakers and other producers that Vimeo is the best way to make money from their content online. In many ways, it’s an uphill battle.

Both Vimeo and YouTube let anyone self-publish video on their sites. But Vimeo makes money selling subscriptions to content makers and giving them control over their product, eschewing preroll ads, which are YouTube’s bread and butter.

Vimeo is a minnow in the shadow of the YouTube whale. The latter’s ad-supported free model is on pace to generate some $5.6 billion in gross advertising revenue this year, eMarketer estimates. Vimeo sales for the 12 months ended in September came in at just $37 million, according to IAC.

How in the world can Clayman and Vimeo fight the Internet’s prevailing content-wants-to-be-free ethos?
YouTube, he said, is like free broadcast TV. Vimeo is like cable in the early 1980s: tiny right now, but with the potential to be a multibillion-dollar biz.

“There’s a mass-market acceptance of over-the-top as a means of consuming video,” Clayman said. “The market for premium content, where people spend $5 to stream a movie or $3 for a series — that’s a market we are just at the beginning of.”

Before boarding Vimeo, Clayman was head of digital strategy for News Corp; he also oversaw the launch of the company’s ill-fated iPad newsmagazine, the Daily, which was folded a year ago after failing to attract enough subscribers. Before that, he was MTV Networks’ exec VP of digital distribution, cutting its first deals with Netflix and Hulu after having led the programmer’s mobile media efforts.

At Vimeo, Clayman wants to grow the base of 400,000 content producers who subscribe to its publishing tools, and make it easier for them to make money from online VOD.

“On one end of the spectrum, you have network TV and studio films. On the other end there’s a broad set of user-generated content,” he said. “There’s so much really, really good content in the middle that isn’t being distributed.”

Unfortunately for Vimeo, many digital-video producers simply don’t consider transactional VOD a viable way to reach a mass audience today. Other players with similar direct-to-consumer paid-video strategies, like VHX and Chill.com — as well as YouTube’s stab at paid channels—have gone nowhere.

Since Vimeo On Demand launched in March, content owners have added 4,000 titles to the store. Vimeo CEO Kerry Trainor said VOD sales to date have been “encouraging” (he wouldn’t provide numbers) but acknowledged that it’s a nascent business. With Vimeo now topping 135 million monthly visitors, the company will turn on the monetization taps in 2014 with Clayman at the helm.

“Vimeo has a big challenge,” said Jay Bennett, VP of digital and creative director at Smokebomb Entertainment, the digital arm of Toronto-based production company Shaftesbury, which uses Vimeo. “YouTube is the big broadcaster. Everyone else is really niche.”

Clayman thinks he’ll be able to change that attitude by focusing on the needs of smaller producers, adding that Vimeo is evaluating new distribution models such as selling video in subscription-bundle packages.

“There are lots of places to see this stuff. It’s not a lack of options,” Clayman said. “The difference is, we know our audience and we want to put this content where it will not get lost in a catalog by a larger distributor.”