Newsletter 101: Writing Content People Want to Read

Kira Colburn
Work-Bench
Published in
4 min readApr 1, 2021

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With Substack on the rise and nearly every company on the planet now writing their own newsletter, it’s more difficult than ever to wade through the mass information being sent to your inbox. However, for any company, email marketing is a key part in growing your pipeline and strengthening your brand.

So the real question is: How do you write a newsletter that will gain loyal subscribers?

Work-Bench’s Enterprise Weekly Newsletter is now 7 years old 🥳 and we’re constantly thinking this through, reiterating on what’s working and what’s not. After countless creative tests, constructive feedback, and the occasional “stop emailing me,” we now reach over 18,000 enterprise techies every Friday, and are excited to continue growing this community.

While there’s no perfect template or one-size-fits all approach, here are our top learnings from creating, writing, and scaling our newsletter over the years:

#1: Define your audience, they’re your new boss

Before you even get that first draft going, you’ll need to define who you expect to read and care about your newsletter’s content.

While this sounds simple, defining an audience is likely more complicated than you realize. To unpack this, ask yourself: Who would benefit from my knowledge? What demographic and industry do they primarily make up? What are their challenges? What drives their success?

Don’t be afraid to get specific here. While you may worry about alienating others, you need to carve out a niche to make your newsletter stand out. Given all the content out there these days, generalization is the enemy. As an example, Enterprise Weekly echoes our brand as early-stage enterprise software investors — so we write for enterprise founders and operators, Fortune 500 executives, and VCs in the space.

Once you have a good grasp of who and where your audience is, it will be much easier to pick out content that caters to them. Honing in on their wants and needs like this will also help foster stronger, longer-term relationships.

#2: Content shouldn’t be all about you

It’s easy to fall into the trap of recapping your company’s updates. While it may feel like your company information is important for your broader audience, chances are it’s usually not. So keep the information about ‘you’ to a minimum — this should not be your newsletter’s primary content.

Instead, put your expertise to work. Focus on the exclusive expertise only you can bring to the table that would help your audience uplevel their day-to-day lives. This could be timely research, industry perspectives, playbooks, etc. Again, just make sure, it’s all tailored to your specific audience’s needs. This content should also be relatively new or have a fresh spin on it, so make sure you aren’t just reposting old news or regurgitating what others in your field have already published.

#3: Success is often in the details

Design

  • Brand your newsletter appropriately. Make sure your logo, fonts and colors all reflect your “brand feel” throughout the newsletter. If someone can read the newsletter and recognize it’s from your company without seeing the logo, you’ve won the branding jackpot.
  • Make it easy to contact you. Include direct contact information somewhere — email, Twitter handle, LinkedIn profile, etc.
  • Keep short, simple formatting. People are busy, so make sure that readers can get the information they need from your newsletter quickly and easily. Use the “inverted pyramid” strategy (include most important news first, trickling down of importance). Creating clear section headers will help with this navigation. This also means, don’t overcrowd your newsletters with too much information.

More on Content

  • Keep the subject line short and reflect the #1 value you’re providing your readers. Subject lines should be less than 100 characters. Keep the emojis, punctuation, and ALL CAPS to a minimum as these are more likely to wind up in a spam folder.
  • Don’t forget to show your personality. While your newsletter should be professional, it should also reflect who you are as a company or individual. Don’t be afraid to throw in a few emojis, linked Tweets, conversational language, photos, etc.

Distribution

  • Set a cadence and stick to it. Set a day and time for your newsletter to be sent out, then meet that deadline. Your readers will come to expect your newsletter in their inbox then. Since COVID-19, Friday has become the most successful day for newsletters in terms of open rates, click-through click-to-open rates.
  • Don’t be annoying. Don’t send out too many emails. Your unsubscribe rate shouldn’t hover much above 0.2%. If you see your unsubscribe rate increasing more than usual, re-evaluate if your newsletter can decrease in cadence.
  • Cross promote your newsletter across all of your branded channels.

Sign Ups

  • Make it as easy as possible for people to sign up. They shouldn’t have to search very long or hard if they’re trying to do this. A few ways to do this include: Create an easy-to-navigate signup page, add a signup box in your website footer, add a pop up signup box to your website homepage, add a signup link to your email signature and social media profiles, etc.

Thank you so much to our loyal readers over the past 7 years — you are the heart and soul of Enterprise Weekly! And as always, if you have any feedback on what content we should feature to make our newsletter even more impactful, we’d love to hear from you.

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Kira Colburn
Work-Bench

Head of Content at Work-Bench, leading the firm’s content vision, strategy, and production!