New York Magazine Jason Sylva on how to launch a paywall

In theory, a flexible paywall allows a publisher’s audience to develop more of a habit, hit advertising campaign goals more easily, and test out more hypotheses. But it also risks confusing readers. In this presentation from Digiday’s Hot Topic: Subscriptions and Commerce, which took place in New York City this past February, hear from Jason Sylva, general manager of consumer marketing revenue at New York Magazine, as he discusses its decision to go with a dynamic paywall. The key hits:

  • Information like when, where and how consumers are interacting with your content can help you determine strategic perimeters for the paywall.
  • When introducing a paywall, many publishers run into problems with it impacting their advertising business. To find a balance, consider leaving the paywall off of one-off pieces, such as television recaps or event coverage, and instead drive it on some of the more in-depth reporting.
  • Optimize, but also learn: Optimizing focuses on existing demand, and learning enables you to build a more sustainable business.

 

 

Listen to this presentation on the Digiday Live podcast here.

More in Media

A subscribe button surrounded by lush green and red tropical plants, symbolizing how publishers cultivate and grow loyalty among their subscribers

Media Briefing: Overheard at the Digiday Publishing Summit, March 2026 edition

With no sign of search traffic returning, publishers are doubling down on subscriptions to build direct reader revenue — but it’s not easy.

People Inc.’s Jon Roberts on the AI licensing boom – and the revenue lag

People Inc’s Jon Roberts discusses the boom in AI content licensing marketplaces — and the revenue that could materialize for publishers.

YouTube is building infrastructure for the full creator-brand partnership life cycle

YouTube’s Gemini-powered Creator Partnerships promises to alleviate pain points in the influencer marketing pipeline.