In part two of our newsletter strategy series, we explore ingenious brands that have carefully crafted their strategy to provide thought-provoking and digestible information, via inbox.

If you ask Lena Dunham if the newsletter is a dying medium, she’d — hilariously — put you in your place. After all, she should know: A few years ago, she launched the uber-popular Lenny Letter, which explores a wide range of topics, primarily relating to female activism and feminism. Now owned by media powerhouse Condé Nast, this weekly distribution is opened — and devoured — by millions.

This niche approach is just one example of personalities, writers and brands who are nailing the art of content newsletters. Though Lenny found near-instant success, thanks to a celebrity founder, sourcing inspiration and ideas from newsletters like Lenny is the best place to begin developing your strategy. Here’s why newsletters remain relevant, and why you should follow the path of those leading the surge:

newsletter series examples of brands that nail with emailss

The need for newsletters

Yali Saar is the CEO of Tailor Brands, which boosts an impressive community of seven million creatives who execute logos, brands and other design materials. As a modern digital company, they’ve pivoted their strategy to reflect the demands of various consumers and companies, and Saar says email content is up there on the high-priority list. “Emails were always a good marketing channel, but over the years we realized that they could also be a way for us to enrich our product and provide extra value to our customer. Newsletters are basically an extension of your product that allows you to bring back customers that might have been lost otherwise,” she explains.

Why not just use a blog? Though many newsletters, including Lenny, do have a .com destination, the bulk of the engagement comes from paging through their inbox, not various posts. As Saar explains, with a blog, the tricky part is getting them there, which isn’t always easy. And sometimes, if your site is wonky or they have a negative experience, you quickly lose your opportunity to keep their attention. Saar says a with a newsletter, you can redo this experience and give him/her a reason to come back and give you a second chance. In fact, she notes many brands and customers are using blogs for SEO-driven goals, and newsletters to actually provide engaging content.

Career coach Jill Tipograph stresses the responsibility of a brand to deliver the newsletter promised — whether you’re a travel journalist providing city guides or a shoe company offering an insider perspective on your production process. This will ensure the newsletter is an engine to meet goals and attract more readers, building your reputation and expertise in your respective industry.

The ultimate goal of any brand is to convert a subscriber or a consumer into a customer, then to build loyalty to encourage repeat business. And lastly, for them to tell others about the brand information and newsletter.

Brands that get it. Take a page out of the rule books of these popular emails and apply them to your best practices.

Branding expert Wendi Weiner says it best when she explains how newsletters can be much more targeted and personalized as a form of content marketing. You can even have various editions — news, travel, food, business, you name it — to ensure you’re reaching the right demographic in the right way. Real-time data also allows for quick edits and retargeting, making the business of emails more fluid and fast.

These brands have managed to curate the experience, resulting in endless subscribers — and sure, fame:

newsletter series examples of brands that nail with emailss


Tipograph describes Lenny as a glimpse into culture and societal moments, trends and issues, but with a special differentiator. Instead of lumping all headlines into one long email, they tackle one topic at a time, weekly — and they attract a slew of impressive writers to develop and share their renowned voices. This sets their content apart, since it is always well-written and provoking.

Apart from smart reads, it also widens the reach of your subscribers, since influential leaders in the content space tend to share pieces of work they’re proud of. And with the seal of approval from Dunham, it is that much more appealing to talented wordsmiths to join the masthead.

“Having noteworthy contributors is a smart strategy to broaden subscriber base and have those influencers cross-promote Lenny articles they write,” she explains. Saar adds Lenny might have a website, but it is secondary to the digest. “Lenny is not directing readers to their website. The content is only through the newsletter, which sets them apart from other newsletters,” she says.

newsletter series examples of brands that nail with emailss


Truth be told, theSkimm has received a bit of negative attention over the years. Created by two 20-something females, its original intent was to make news easier to digest for busy women. Many feminists weren’t too keen on the notion that women couldn’t read traditional news articles on their own, but as the company has grown, they’ve managed to turn opinions and attract more subscribers.

Tipograph says their approach is best described as a daily quick rundown of what you need to know, either for yourself or to chat about with others. The notion is if you’re about to attend a networking function, a dinner party or have an interview, you can quickly “skim” (get it?) and have a basic understanding of the headlines. “It’s hard to keep up with all today’s news in all sources, so theSkimm does a nice job of providing a quick read, in under a minute or two,” she praises.

It also helps that theSkimm chooses a quirky, sometimes dark, and sassy voice to deliver information. As Saar says, with a visually-engaging design and a sufficient format, they’ve created a unique message sets them apart from other major news outlets that might share the same information. Like Lenny, the content of theSkimm is only available for subscribers, so you can’t surf the web and find it.

newsletter series examples of brands that nail with emailss


This company is a triple threat: offering blogs, newsletters and a bare-bones CMS system. Many companies have switched their blogs off of WordPress in an effort to make syndication easier between brands. Medium’s ability to cross-promote content that’s sourced from writers or companies and potentially help them go viral is a big difference compared to other companies in their space.

As Saar says, it’s the vast size of Medium that allows them to execute a compelling newsletter strategy, across a wide spectrum of topics. “Medium is such a large and diverse platform that it is important for the newsletter to aggregate the most interesting and relevant highlights to draw their readers onto the site itself,” she explained.

Unlike Lenny or theSkimm, Medium’s goal is to drive traffic to their website, but they do it by catering to various interests. Their Daily Digest newsletter takes the best, trending headlines and delivers them daily into your inbox. This allows you to know what narrative headlines are about to be discussed in your friend circle. Another perk of Medium is targeted specifically for writers who want to develop their own newsletter strategies. If a reader likes a particular journalist or blogger, they can subscribe; meaning each and every time they publish on Medium, that person will be notified. The bonus of that? More eyeballs and traffic, of course.

newsletter series examples of brands that nail with emailss

The Muse

This job board posts gigs, of course, but their content strategy speaks for itself. They deliver dozens of new articles a day, tackling all sorts of topics regarding professional development, interviewing, upward mobility and more.

As a subscriber, Weiner says one of the most impressive and consistent techniques The Muse uses is optimizing their subject line. “They always have a killer subject line to really grab your attention/ And it’s relatable content — that every audience member can empathize with. There aren’t sales pitches involved per se, and they are truly targeting job seekers with current trends, and ‘how to’ tips,” she explains.

This authenticity isn’t veiled with a promotion, and Weiner finds it to be knowledgeable information that’s packaged smartly. “If the headline is about remote work, the articles included are targeted around that subject matter. This makes it a much more centralized focus for the reader, instead of having a newsletter that focuses on multiple different subject areas,” she explains.

While their audience is more niche since it’s about folks looking for a new gig, readers are more likely to stick around even once they receive an offer letter, since they’ve enjoyed the content.


Be a content hero


   Newsletter Strategy Series