Building effective strategies for creating engaging e-mail newsletters

By Shelley Seale


Austin, Texas, USA


Dan Oshinsky, founder of Inbox Collective, presented a workshop at INMA Media Subscriptions Week to delve into best practices for engaging readers and driving subscriptions through newsletters.

“I can’t believe this is 2020, and I’m still saying this,” Oshinsky opened. “E-mail is one of the most important and engaging tools, and many still aren’t taking advantage of it.”

Why invest in e-mail?

E-mail is a tool for creating relationships with your audience. “Done well, it’s a tool for actually building one-to-one relationships with your readers,” Oshinsky said. “If you get an e-mail address today, you can have a relationship with that person today, tomorrow, next week, or next year.” He added that the e-mail inbox is one of the few digital platforms that isn’t owned or controlled by players like Google and Facebook: “You own it.”

E-mail is a living room. Oshinsky compared e-mail to broadcast news channels on television and the relationships they have with their loyal audience members — who may start or end their day with them, or both. Audience members feel they know the news anchors, and the e-mail inbox is a similar way to get “in the living room” of your target audience.

“Subscribers allow in a handful of lucky guests — family, friends, and maybe your brand,” Oshinsky said. “Take advantage of the one-to-one nature of the inbox. I always think of the inbox as this living room. If you do it well, you have a chance to stay there for a very long time.”

E-mail is a cross-functional tool. “It’s a rare tool that you have that touches every single part of your work.” It plays a key role in many parts of your growth strategy: It can drive traffic, grow your audience, build habit, increase loyalty, reduce churn, and convert readers to subscribers.

E-mail drives revenue for your organisation. “I see news organisations around the world invest in e-mail because it’s such a powerful tool to drive revenue,” Oshinsky said. “E-mail is an amazing tool for getting readers to your site.”

Dan Oshinsky of Inbox Collective led a workshop at the INMA Media Subscriptions Week on driving e-mail engagement.
Dan Oshinsky of Inbox Collective led a workshop at the INMA Media Subscriptions Week on driving e-mail engagement.

How to create e-mails that readers love

Oshinsky shared his top five rules for creating engaging e-mails that get results:

Rule 1: Content is king, but distribution is queen (and she wears the pants). “The storytelling and work that you do is very important, but equally important is getting that work to your readers,” he said.  Media publishers own that channel and the relationship with their readers.

Rule 2: Create habits and routines. Some companies send e-mails at exactly the same time or on the same days, so readers know when to expect it. That creates a habit.

Rule 3: Start with a building block. Oshinsky mentioned four essential ones:

  • Identity: Who you are and what you care about.
  • Service: The things you want more of on a day-to-day basis.
  • Utility: The things built around the information you need more of on a daily basis (government, school and road closures, weather, etc.).
  • Personality: Many news organisations have started building personality-driven newsletters, with the tone and voice of their brand or specific journalists.

Rule 4: Trust is hard to win and easy to lose. “People are used to being bombarded with e-mails they didn’t ask for or want,” Oshinsky said. “Build e-mails that readers really want.”

Rule 5: Remember that direction is more important than speed. Where you are going is more important than how fast you get there. It takes time to build up a great e-mail program, and to figure out how to monetise and test it.

Deciding which e-mail products to launch 

All of this information is great, but where does an organisation start? “Let me define the five main categories of newsletters,” Oshinsky offered.

  • Traffic-driving newsletters: Primarily designed to drive readers to your site to read a story.
  • Destination: These are designed to be read in the inbox. The destination is the newsletter itself. They might link to your site, but the primary goal is to deliver value to the readers without requiring them to click.
  • Alerts: These alert a reader when a certain type of story goes up. This could be breaking news, a new article from a featured writer, or covering a specific topic. These are good for driving habit.
  • Courses: These are an automated series of e-mails that get triggered after a certain action. They are designed to teach a new skill, habit, or lesson.
  • Pop-up products: These only run for a limited time. They are designed to inform or educate around a specific event.

Getting Started: Launch a daily newsletter

“Launching a daily newsletter is a great way to start and to test,” Oshinsky said.

A great daily newsletter does the following:

  • Builds habit.
  • Drives daily engagement.
  • Can be incredibly effective at converting casual readers to paying supporters.
  • Can help reduce churn.

Getting started: Launch an onboarding series

A great onboarding series will accomplish four things :

  • Establish a relationship with the reader.
  • Guide that reader through the next steps on their journey.
  • Drive engagement from Day One.
  • Improve inbox placement for your newsletters.

Getting started: Launch a personality-driven product

The best personality-driven newsletters will:

  • Showcase unique voices in your newsroom.
  • Reinforce the value of your organisation.
  • Serve specific audiences — not verticals.

Oshinsky then opened up the presentation to the audience for workshopping these ideas. “I want to get you away from thinking about verticals, and think about audiences and services instead.”

INMA members attending the workshop were encouraged to think about the following and complete it on a worksheet handout (you can download the worksheet here). 


  • Who your readers are.
  • What they care about.
  • What they do.
  • What they like and dislike.


  • What readers need from you.
  • What you do uniquely well.

How to measure success

Start by tracking your open rate — but focus on unique open rate, which measures the unique number of subscribers on your e-mail list who opened a specific e-mail.

“Unique open rate is what I care about most,” Oshinsky said. “I’m trying to convert them, so that’s the metric that’s most important. It’s also the most accurate.”

He also advised people to check with their ESP to see how they measure this and to understand what the metric actually means.

Other metrics to monitor include:

  • Monthly list growth.
  • Click-to-open rate.
  • Habitual readers (the percentage of readers who open 50% or more of their newsletters per month).
  • Engaged minutes per newsletter, which is the amount of time a user spends on your site after clicking through from a newsletter. Unfortunately, tracking engaged minutes of reading inside the inbox is practically impossible today.
  • Mobile open rates.
  • Clicks per thousand e-mails sent.
  • Conversions to paid subscribers.

Oshinsky invited INMA members to request a handout created especially for this workshop: Five steps to improving your e-mail program in 2020, which you can access here. He also invited members to read his monthly Google Doc, Not a Newsletter.

About Shelley Seale

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