Converting a reader to a paying subscriber is just the first step in the journey. What you do in the next 100 days after that dictates whether you will keep that customer for years to come — or let them slip away.

Your onboarding process is the key to help newly subscribed readers discover the value of their subscription. In a Webinar on Tuesday, Dan Oshinsky of Inbox Collective shared strategies with INMA members on improving that subscription journey, from onboarding new subscribers to tactics for building habit with readers through newsletters, along with metrics teams can use to measure success.

Oshinsky knows a few things about this. The former director of newsletter at BuzzFeed and The New Yorker now runs the consulting firm that helps news organisations grow their audiences, build relationships, and drive revenue — all through e-mail.

“The first 100 days are absolutely critical for success,” Oshinsky said. “It’s when readers are most likely to adopt a new feature, it’s when readers are most likely to be highly engaged with your product — and if you build that early engagement, they’re likely to stay engaged for a very long time.”

Most monthly subscribers are most likely to churn in the first three months, he added. Why does this happen? Most likely, it’s because the company hasn’t done enough to build the relationship with the subscriber in that critical onboarding period.

Oshinsky urged news media people to consider it like a “dinner party strategy.” Imagine you are invited to a dinner party where you don’t know anyone. What would you want the host to do to make you feel welcome?

Introducing people, making sure they meet other people at the table, and pointing out common interests are some effective tactics a host would use in this scenario. 

“I might go to some real lengths to make sure they feel welcome and warm,” Oshinsky said. “I would make sure they know how to find the bathroom and the kitchen — how to navigate the home so they have a good time. Building an e-mail strategy for the first 100 days after they subscribe is a little like that.”

He shared the major goals news publishers should have during that first 100-day period: 

• Educate subscribers about your newsroom.

• Build reader habit.

• Establish the relationship with the reader.

• Learn more about their needs and interests.

• Make it convenient for them to incorporate your newsroom into their lives.

• Help them understand the value of your work.

With those goals in mind, Oshinsky shared 33 practical tactics that INMA members could use in their onboarding process to keep that subscriber long-term.

1. Immediately offer a CTA

As soon as a reader completes their subscription, give them a chance to engage with you on your key platforms. E-mail newsletters are a particularly good ask because you’ve already collected their e-mail address and therefore can encourage a one-click subscription.

“I love what The Economist does,” Oshinsky said. “They have three things they show immediately after you become a paying subscriber.”

1. Nudge the subscriber to choose newsletters to sign up for.

2. Encourage them to download the app.

3. Nudge them to start reading.

2. Thank them for their subscription

“A lot of organisations miss this,” Oshinsky said. 

He referenced Bloomberg as a good example. Immediately after subscribing, a new customer receives an e-mail from the editor-in-chief, thanking them for subscribing to Bloomberg journalism.

Whether the customer is paying US$1 or US$500, make sure they understand your appreciation. This is also a great place to give them a CTA to take a next step. Bloomberg provides this at the bottom of the editor-in-chief e-mail, with buttons for listening to podcasts, subscribing to newsletters, and so on.

3. Add them to your daily newsletter

Building habit is vital, and one of the best ways Oshinsky has found to do this is through a daily newsletter. This allows readers to see the best stories and build a daily reading habit. These often go out at the same time every day.

Depending on your location and regulations around this, consider automatically registering a new user for this daily newsletter or giving them a clear chance to opt-in.

“As they start to build that habit and think of you as a destination to go to every day, those people are unlikely to churn because they’re getting the value of your newsroom every single day.”

4. Tell them more about your mission

After the initial thank-you e-mail, perhaps three or four days later, Oshinsky suggests sending an e-mail from a key editor or member of the team to give more information about the publication and its values and mission.

Make sure the e-mail comes from that specific person, not just the organisation in general. These can be simple — they should look like an actual letter, not like a marketing piece.

“Readers respond really well to these, and the open rates are very high,” he said.

5. Introduce your staff

A few days later, consider sending an e-mail that introduces the staff. This establishes trust with readers by showcasing the newsroom’s unique voices and personalities.

This can be done in a single e-mail or through a series of e-mails from different staff members. Consider allowing the reader to choose who they want to get e-mails from or personalising the series based on their reading habits.

6. Drive a +1

Oshinsky defined a +1 as one more thing you’d like the subscriber to do to engage more deeply. This could be signing up for a newsletter, liking a social media channel, downloading the app, or connecting on WhatsApp.

Focus on opportunities to build habit and encourage subscribers to share your products with their network, increasing your exposure through personal recommendation.

7. Learn about their interests

This is crucial, Oshinsky said. To build a relationship with a subscriber, a news organisation must identify the subjects they care most about.

He shared an example from the Sightline Institute that comes in an e-mail from the executive director. Towards the bottom of the e-mail, he asks the reader to click on the issue they care most about. This is followed by a bulleted list of four major issue topics.

The beauty of this is the subscriber can provide this valuable feedback very easily with a simple click. This information can also inform the rest of the onboarding journey with that user.

8. Bring them your best stories

Don’t assume that readers know what your best content is. Oshinsky referred to his time at The New Yorker, where the team felt each subscriber knew everything about the publication.

“They know our history, they know our background, we don’t need to tell them this stuff,” he recalled about his team’s line of thinking. “But I was surprised by how often we would send e-mails to readers about things like a podcast and readers would go, you guys have a podcast?”

They found readers didn’t know The New Yorker had crossword puzzles or that some stories on the Web site were different from the stories in the magazine.

“Readers, it turned out, didn’t know a lot about what we did. So assume that many of your readers might not be aware of your best work. Bring the stories to them.”

9. Ask readers questions

One of Oshinsky’s favourite examples of this comes from The Chicago Sun-Times. In its afternoon newsletter, they feature a daily question with reader replies. For example:

“How do you feel about Scottie Pippen taking shots at Michael Jordan and the Bulls in his new memoir? Reply to this e-mail (please include your first name and where you live) and we might feature your answer in the next afternoon edition.”

True to their word, the next afternoon newsletter features a selection of some readers’ replies and commentary.

The Ottowan asks readers for their favourite local restaurant. An astounding 80% of readers respond with an answer.

10. Poll them and ask for feedback

Simple questions to readers are a good way to build the relationship. These can be done in newsletters, on a social channel, or via text message. If the reader clicks through, take them to the Web site to answer more questions or nudge them to read relevant stories.

11. Give the reader a chance to receive alerts about their interests

These are good ways to help readers build habit, see your best stories, and understand the value of what you do. These alerts can be about breaking news or tied to a notable writer or personality. 

Consider offering these alerts via e-mail, push notifications, text, or in the browser.

12. Drive them to engage on your social channels

Make sure readers know how to follow your newsroom, either via a dedicated e-mail in the onboarding series or on your Web site. Give clear CTAs to follow your staff on social pages.

Putting journalists’ social media handles in their bios is also a great way to increase that engagement. This is just another channel in which to build habit.

13. Encourage them to share tips and story ideas

Ask readers to share their ideas directly with the newsroom. Consider adding spaces on individual stories for readers to share their feedback, questions, or ideas — particularly local issue content.

“These sorts of stories are great to collect information,” Oshinsky said. 

One publication, The Lookout, includes a newsletter subscription checkbox at the bottom of its sharing ask: “There’s a grow tactic as part of that.”

14. Get them to listen to your podcasts

“You have them — make sure people know about them. Include CTAs on your Web site as well. Maybe you want to send a dedicated e-mail about these or nudge them as well,” Oshinsky said.

Make it easy for readers to subscribe on common podcast apps.

15. Encourage them to download your app

An app shouldn’t be there just for the sake of downloading. Make it really clear to readers what the benefits are of using the app. Some of these might include:

• A cleaner reading experience.

• Audio exclusives.

• Push alerts around key topics.

• Personalised content.

“Everyone has an app these days. What is the value [to the user]?” Oshinsky said. “Getting someone to have that app on their home screen we know is incredibly valuable because the apps on their home screen are the ones that are seen. People who use your app are power users of your site and are highly unlikely to cancel.”

16. Give them opportunities to try games or puzzles

Be sure to broadcast if you offer puzzles or games. These are high-engagement products, and readers who regularly utilise them are typically far less likely to churn.

Consider launching alerts (e-mails or app push notifications) to help readers build the habit of playing games.

17. Build a weekly news quiz

This is a nice way to remind your readers of what they learned from your content during the week. It’s an easy entry point for the reader into the news and might inspire them to read more deeply on certain subjects.

After a reader finishes a quiz, give them the chance to subscribe to relevant products such as podcasts, newsletters, or social media channels to keep them informed.

18. Invite them to exclusive events

Make sure readers know about opportunities to attend events — and be sure it’s clear which ones are subscriber exclusive.

The Marshall Project, for example, kicked off a special journalism series on the Rikers Island crisis with a special online briefing event that was exclusive for subscribers. Registration was required, and the event was broadcast through subscriber e-mails.

Others include things like The Wall Street Journal’s live cooking classes, exclusively for WSJ+ members. Publishers could consider launching exclusive events for subscribers, but they don’t have to be fancy or require a lot. A monthly call with editors in which readers can ask questions of staff is simple, but powerful.

19. Encourage them to text your staff

SMS messages are a good way for readers to interact with reporters. Oshinsky reported text messages not only have high open rates, they also have high engagement rates.

“It’s such a personal space,” he said. 

Ask readers questions and ask them to text back their replies. This can be done via SMS but also via apps such as WhatsApp and Telegram.

20. Ask them to vote for their favourite things

People love to share their opinions. Brackets or contests work well here, allowing readers to engage around issues they care deeply about, and local topics.

Oshinsky recommends “Best Of” programmes as a low-cost way to drive early engagement and remind readers of your connection to the community. This can be anything from best restaurants or museums to other features in your community.

21. Launch a monthly, subscriber-only e-mail

This is another low-stakes initiative that works really well. Subscriber-only e-mails take readers behind the scenes of what’s happening in your newsroom and connect them with staff they wouldn’t otherwise hear from. These can also be used to introduce new members of your team.

“Someone who reads these sorts of stories are being reminded that there’s incredible value in their support,” Oshinsky said. “I support this newsroom and look at the things they are doing because of my support.”

22. Ask a subscriber to share their subscription with a friend

Readers who give a gift subscription are likely to feel like they get great value for their money. Consider giving subscribers the benefit of allowing a bonus user to their account or to gift a subscription to someone else as part of their package.

This multi-user approach also helps when a user considers cancelling. If they have a friend or family member who is also a user, they might be more hesitant to cancel because that other user is getting something out of it.

23. Nudge them to leave their first comment

Oshinsky points out The Guardian as a news brand that handles comments well. They promote stories that have the most comments and active threads, which encourages more people to both read the story and jump into the discussion.

24. Remind them of the impact of your work

Going back to earlier tactics, continuing to remind subscribers of the impact your journalism has keeps them thinking about the positive change your reporting creates.

These stories remind readers of the crucial role your newsroom plays in their city or region and how their support enables this work.

25. Offer rewards or prizes

Give readers an incentive to engage with you. Offering a reward or giveaway in exchange for engagement is one way to help build habit early in the subscription relationship.

The Salt Lake Tribune does this in an e-mail to subscribers, asking the reader if they’ve explored the food and dining coverage and if there is a restaurant or food business the reader thinks they should cover. A link is provided to e-mail these suggestions to, and the first five responses receive a gift.

26. Alert them to new product launches

Oshinsky highlights this as particularly important.

“Whenever you are launching new things, particularly in the first 100 days, make sure you’re nudging people on your site or via the channels you have.”

Paying supporters should be the first to know about these new products, whether they are a podcast, newsletter, interactive, puzzle, etc.

27. Let them know about big news stories

“Make sure readers know about big stories,” Oshinsky said. “This is something we did a lot of at The New Yorker and it worked really well.”

Particularly with important investigative pieces or deeply reported feature stories, they should be highlighted to subscribers. The more they see such exclusive content on your site, the more they understand the unique value you provide.

“Even if they don’t click, they see we’re doing this and there’s value in this — and value in their subscription,” he said.

28. Help them register with a single click

Existing subscribers shouldn’t have to log in or enter additional information. You already have their e-mail address — they shouldn’t have to go through the process of filling that out and registering again.

Offer personalised recommendations for products, events, or stories to read that they can access with a single click.

29. Survey your subscribers

A survey is your chance to solicit feedback and commentary, as well as identify opportunities to improve your product. 

This is also a chance to identify unhappy readers and target them with campaigns or conversation to engage them before they decide to churn.

“This is a really great opportunity to learn about them and identify people who might be unhappy with their subscription,” Oshinsky said.

30. Offer them chances to opt down if they aren’t engaging

Daily products can be too overwhelming for some people.

“Maybe they’re on a daily newsletter, for instance, and they say a daily newsletter is just too much,” Oshinsky said. “Let’s identify the people who aren’t as engaged and say, do you want to get an e-mail once a week? Once a month? I would rather keep you in the loop in some way than lose you entirely.”

Offer them a chance to move to a channel that makes more sense for them.

31. Launch newsletters from their favourite writers

This gives subscribers the chance to get close to the experts and personalities in your newsroom. Make sure these newsletters offer opportunities for the subscriber to start a conversation with the staffer.

32. Build courses to help subscribers go deeper on certain topics

These are on-demand products that help a reader learn a new skill, habit, or lesson. WBUR, for example, launched a course to “Become an Informed Voter in 7 Days,” which helped its readers to learn about the issues that would be on an upcoming ballot.

33. Celebrate your wins and milestones with subscribers

When you win awards or reach certain milestones, make sure you celebrate them with your subscribers. Make sure they know they are part of your success and that these achievements aren’t possible without their support.

“I know this is a lot,” Oshinsky said in conclusion. He encouraged members to subscribe to his Not a Newsletter or to e-mail him.

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