The New Yorker, an American weekly magazine founded in 1925, with a signature mix of reporting on national and international politics and culture, reviews, and cartoons, amongst other topics, appointed Dan Oshinsky in 2017 as their Director of Newsletters focusing on growing The New Yorker’s relationship with its readers through their multiple newsletters. With GEN, he shares his knowledge on best practices, new challenges, and why email is at the heart of The New Yorker’s editorial strategy.

Global Editors Network
May 2 · 7 min read

If you want to keep up with the latest trends and insights in the journalism industry, newsletters are the way to go. Or are they? Today, readers expect more from a newsletter — more content, tailored to their interest, more insights and exclusivity. A good newsletter has become vital for newsrooms and readers alike, and an organisation’s strategy to grow its newsletter is more essential than ever. To have a look behind the scenes of how newsrooms are keeping up with these demands, the Global Editors Network talked to Dan Oshinsky about the editorial process at The New Yorker of coming up with new newsletters and newsletter ideas, how to monetise free newsletters, and his advice on audience engagement.

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GEN: A Director of Newsletters — what does that entail? What ‘newsletter strategy’ does The New Yorker have and what are some key findings you can share from your experience?

Dan Oshinsky: I oversee the newsletter strategy for The New Yorker — everything from launching new newsletters to content strategy to list growth. Our strategy is simple: To build products that help us to bring our best stories directly to readers. We try to launch newsletters — from our daily newsletter to newsletters around humour, culture, or commentary — that will serve our readers and subscribers well.

Can you share a bit more about your everyday routine? What goes into the process of coming up with new newsletters, or newsletter ideas? Are you the one deciding on the content, do you have brainstorming sessions within the team to agree on what goes into your newsletters?

Most days, I’m in conversation with a handful of key stakeholders, from New Yorker editors to members of our audience development, consumer marketing, product, or sales teams. I’ll check in with key members of the editorial team who are curating content for each newsletter, and make sure they have what they need for the day’s newsletters. I’m also always monitoring our stats to see what learnings I can share with the team.

When it comes to new newsletter ideas, it’s a group effort. We’ll convene a group of editors, talk about questions in this Newsletter Strategy Positioning Brief, and try to come up with concepts that work. Every new newsletter will have an effect on our subscription and sales efforts, so those teams will be part of the conversation, and audience development helps make sure we’re focusing on the right strategies and metrics for our newsletters. We’ll make a few test newsletters and get feedback from the team before we decide to move forward with any new launch.

Click on the picture to read more about The New Yorker’s Newsletter Strategy Position Brief

Do you see it as vital for newsrooms today to have one/multiple newsletters?

Yes, definitely! For an organisation with a broad mission, like The New Yorker, it probably makes sense to launch several newsletters that serve different interests or audiences.

Some debates are ongoing about email newsletters being a way forward for digital journalism to grow an audience. How do you see that comment? Do you believe the medium of newsletters has started growing stronger?

At The New Yorker, email is at the heart of our editorial strategy. Our email audience is one of our most loyal audiences — they spend far more time reading the website newyorker.com than the average reader. Email represents a huge opportunity for any newsroom to build, grow, and retain an audience. Readers — especially our paying subscribers — expect a lot from The New Yorker. Newsletters allow us to deliver our best stories to readers, and to build a stronger relationship with them. For readers who are fans of a particular section of The New Yorker — like fiction, food, or our crossword puzzle — the newsletter is a great way to discover more content that they’ll love.

By The New Yorker cartoon editor Bob Mankoff

There has been a sharp increase in editorial newsletter production in recent years, both by “legacy” print and newer digital media publishers. Is it possible that there are too many newsletters coming from all different directions, leading to market saturation?

No, I don’t think so. But I will say this: Readers expect more from a newsletter than they did five or ten years ago. They expect a design that’s going to be easy to read on a mobile device. They expect additional content, analysis, or insight, some of which may be exclusive to that newsletter. And they expect the stories in the newsletter to be tailored to their interests. In the long run, organisations that focus on creating exceptional newsletters will be the ones that succeed in this space.

Speaking of the future of digital journalism, where does the newsletter have its place? Have you seen a big change in the market in the last year(s), and where do you see the newsletter model can develop further?

Far more news organisations are investing in newsletters, which is exciting to see! When I started as the first newsletter editor at BuzzFeed, in 2012, few newsrooms had employees dedicated full-time to email. Now, it’s a surprise to see news organisations that don’t have an email lead — or even a team devoted to email! I’m thrilled to see more newsrooms investing in newsletters. They have the potential to be traffic and revenue drivers for just about every news organisation.

Newsletters have shown to create audience engagement, but is there a negative side to it? Do we risk creating ‘filter bubbles’ by focusing on target audiences/deliver targeted content?

So many readers subscribe to a publication — say, their local newspaper — because of a specific type of coverage. (For instance: I still subscribe to my hometown paper because it does the best job of covering the local sports and politics that I care about.) Creating newsletters around those areas of expertise is a great way to deliver value for those highly-engaged readers, and it presents an opportunity to expand your audience. My advice: Invest more in things you already do uniquely well.

Consumer engagement is one of the most important pieces of the media industry’s revenue puzzle. So how can newsrooms potentially go about monetising from free newsletter subscriptions?

At The New Yorker, our newsletters are free — but we know that someone who signs up for one of our newsletters is far more likely to become a paying subscriber. So for us, a free newsletter presents an opportunity to bring a reader one step closer to subscribing.

But we monetise newsletters in several other ways. Advertisers love our newsletters, since they’re able to reach a highly-targeted and highly-engaged audience. Our events team loves our newsletters, since we can use them to drive readers to buy tickets for live events, like The New Yorker festival. Our merchandising team loves newsletters, since we can promote our online store, where readers can buy prints of their favourite New Yorker covers or cartoons. We’re also able to drive affiliate revenue in certain newsletters.

You started your project ‘Not a Newsletter’ — What is it about? And why in a Google doc?

Not a Newsletter is a monthly briefing where I share ideas and tips about how to send better email. If you’re interested in building a newsletter program — or hoping to improve the newsletters you already have — I hope you’ll be able to learn something new from it every month. I publish it monthly in a Google Doc — it’s a bit of an unusual publishing platform, I know! — because it’s so easy for readers to share the doc with their colleagues. Readers can also sign up here to be alerted when a new edition of Not a Newsletter is live.

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Interview with Dan Oshinsky by Alexandra Peng.


Dan Oshinsky is the Director of Newsletters at The New Yorker. He’s also the creator of Not a Newsletter, a monthly briefing with news, tips, and ideas about how to send better emails. Before that, he worked as the Director of Newsletters at BuzzFeed, and founded Stry.us. He’s a graduate of the University of Missouri.

Global Editors Network

The Global Editors Network (GEN) is a community committed to sustainable journalism and media innovation. GEN runs different programmes: Editors Lab, Startups for News, and the Data Journalism Awards.

Global Editors Network

Written by

The Global Editors Network is an international association of editors-in-chief and media executives. We foster media innovation and sustainable journalism.

Global Editors Network

The Global Editors Network (GEN) is a community committed to sustainable journalism and media innovation. GEN runs different programmes: Editors Lab, Startups for News, and the Data Journalism Awards.

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