Anne Fleshman, Director of Marketing - Demand Generation at Autopilot

Eloise Shuttleworth, Customer Success Manager at Autopilot

Lesson 1: Stay Top of Mind with Newsletters

Email has three times the users as Facebook and Twitter combined, and people spend about 13 working hours in their inboxes each week.

Whether you’re a solo real estate agent, boutique marketing agency, family-run restaurant, or a venture-backed tech startup, an email newsletter is a strategic place to start your email marketing efforts. Newsletters are a cost-effective, reliable, and time-tested way to keep your brand top of mind with subscribers, distribute your best content, increase website and blog traffic, and drive sales.

In this lesson, you’ll learn how to:

email newsletter
Follow these 8 steps to stay top of mind with email newsletters

Define your audience and set a newsletter goal

You’re convinced—an email newsletter is a marketing must-have. But before you jump in, ask yourself two important questions: Who will read my newsletter, and what do I want to achieve by sending it? Your answers will drive your newsletter content and creative framework as well as its ongoing, measurable success.

1. Who will read my newsletter?

Email newsletters are sent to people who have opted into receiving marketing communications from your brand. This covers a wide range of contacts, but may include paying customers, hot prospects, blog subscribers, cold leads, partners, and influencers. Noticing patterns in your customer base and understanding what need brought them to you is the first step towards crafting compelling newsletter content.

Study your reader’s profile, their primary challenges and priorities, how they prefer to consume content, why they buy your product and/or service, and what they’d expect from your newsletter. Then, write a sentence that describes three benefits of subscribing.

For example: 

  • Sign up to get recipes, receive special promotions, and hear about events (Golden Boy Pizza)
  • Sign up for tips on how to approach the buying process, market trends, and new property listings in your area (Solo real estate agent)
  • Sign up to learn about upcoming growth marketing events, new features, and how you can successfully take your marketing on Autopilot (Autopilot)

This exercise will bring clarity to your audience. It will also empower you to craft newsletter content for your market-center customers—the 80% who have the most to gain from your offerings and are most likely to respond to your email marketing efforts.

2. What do I want to achieve by sending a newsletter?

Most marketers pay attention to standard email performance metrics, such as open and click rates. But it’s important not to lose sight of the bigger picture.

Set a newsletter goal that goes one step further. You could aim to improve product usage rates, steer customers toward repeat purchases, drive conversations on social, or ensure a regular cadence to maintain healthy brand awareness and strong reader relationships.

Establish an adequate newsletter frequency

In our 2015 marketing automation performance study, Autopilot learned that companies that send marketing communications to customers every two to four weeks generate twice as many leads. Surprising? We don’t think so. Maintaining a regular email newsletter sending schedule helps readers know what to expect from you. It also gives you a deadline to meet.

Over-communicating with your contacts doesn’t come with any obvious diminishing returns. Having said that, it’s important not to spam your community. As John Jantsch from Duct Tape Marketing puts it,

You definitely want to establish a routine of expectation–say a weekly newsletter or roundup, but you want to be careful not to abuse your list with every good offer you can pound away at.

For this reason, we recommend sending a newsletter to your subscriber list at least once a month. This puts you in the sweet spot of staying in touch frequently enough to double your leads, while giving you enough time to craft the right message and offer for your audience. Leaving more than four weeks between sends puts you at risk of being out of sight, out of mind.

But what about specific days and times of the week? Is there an optimal time to send your monthly newsletter? The answers are rather subjective and depend a lot on your audience, industry, and geographic location.

Companies that send marketing communications to customers every 2-4 weeks generate twice as many leads

At Autopilot, we’ve tested different time and date theories. For day of the week, we found our audience responds 18% better to newsletters sent on a Tuesday or Thursday versus Wednesday or Friday. For time of day, we saw the best results from sending at 8 AM PST.

You can do many tests to determine what’s right for your company and audience—and we highly recommend that you do so. You could also try MailChimp’s “Send Time Optimization” tool, which suggests the best day and time to send your campaigns.

Our key takeaway? Try experimenting with personalized newsletter send times and content by segmenting your audience based on location and topics of interest.

Deliver effective newsletter content

So you’ve defined your audience, goal, and send frequency. Now comes the exciting part: Creating your content. How do you ensure it’s compelling enough to both win your customers’ affections and drive business results?

Our guiding principle is to out-teach the competition. Focus on delivering useful, educational content packed with insights that will bring your readers success in their lives and careers. Sounds easy, right?

Don’t be put off by this task. Next, we’ll outline three sure-fire approaches for delivering award-winning newsletter content.

Focus on delivering useful, educational content packed with insights that will bring your readers success in their lives and careers

The original content approach

If you have the time and resources, create brand-new content for each newsletter tailored specifically to your readers. The benefit is that your sponges (people that read every word of your email) will have an experience that keeps them wanting more. The downside, for smaller companies in particular, is that this approach puts pressure and a time commitment on dedicated copywriters to consistently create original content.

The digest approach

An easier approach, that many companies have adopted with great success, is creating a newsletter by compiling fresh blog and online content, also known as the digest approach. The benefit is that you can repurpose content you’ve already created, such as top-performing blog posts, customer stories, and infographics.

Here are some digest newsletter examples to spark your imagination:

These newsletters all feature multiple sections and calls-to-action, but use different email templates.
digest newsletter examples

While each company uses a different email template design (more on that later), every newsletter has multiple sections and call-to-actions linking to content that lives on the company’s website and blog as well as outside sources.

The curation approach

If you feel like you don’t have enough content, don’t let that stop you from sending newsletters. Many have built their contact databases and driven sales simply by curating links to relevant content from around the web. The value-add to your customers is that they don’t have to go out and find these links themselves. They trust (and expect) you to do it for them.

Over time, you may find that your email newsletter becomes a combination of all three approaches. The common thread here is that timely insights, stories, and news will keep you top of mind and allow you to build trust with your subscribers.

When it’s time to buy, your audience will come to you because you’ve provided value through teaching, not selling. Remember: Writing infomercial-like content that overtly (or even indirectly) focuses on selling your own products or services will turn off all but the most motivated buyers. 

Writing infomercial-like content that overtly (or even indirectly) focuses on selling your own products or services will turn off all but the most motivated buyers

Write open-worthy newsletter subject lines

Your subject line is arguably the most important part of your email newsletter. It drives open rates, after all—and zero opens means no exposure for your original, digest, and curated content.

Take time to craft something that compels your subscribers to open and read your newsletter. Follow these tips to boost your results:

  • Keep it short. Subject lines with six to 10 words generate the highest open rates.
  • Use the reader’s first name in the subject line as per email personalization best practices. Personalized emails are known to deliver six times higher transaction rates.
  • Avoid spam trigger words in the subject line, like “credit”, “discount”, “gimmick”, “obligation”, and “click here”. (See more spam trigger words.)
  • Summarize what’s inside. For example, “–First Name–: high growth, dilemmas, and secrets inside”. Or go the route of putting “Weekly digest” or “Monthly newsletter” at the beginning of the subject line, followed by what’s inside. The subject line of a recent Typeform newsletter using this technique was “September round-up: outperforming the competition by 20%—with happiness”.
  • A/B test your subject line and take note of what performs well from each send. 
Take time to craft something that compels your subscribers to open and read your newsletter

Design a best-in-class newsletter template

Invest in designing a newsletter template that is worthy of your brand. Readers want to be presented with something that’s visually appealing and easy to digest. There are many examples of beautiful newsletters that can help jog your creative process. Once you’ve nailed a minimal viable layout, you can then swap bespoke content each time you’re preparing a newsletter send and evolve your design over time based on experimentation.

When choosing a newsletter template, you have three options:

Option #1: Create a plain-text email template

While HTML emails are the most popular route for email newsletters, text-based emails are a viable option. They’re also much easier to develop, and can create a more personal experience because they feel like an email you might receive directly from a friend or colleague. The main con is they lack logos or branding.

Here’s an example from our friends at Segment:

This plain-text email newsletter was sent to thousands of contacts yet maintains a personal touch.
Source: Segment
segment plain text email

The above newsletter was sent to thousands of contacts in Segment’s community, yet the email maintains a personal touch. What plain-text emails lack in aesthetics, they make up for with ease of creation. If you can write a normal email, you can create a plain-text newsletter.

Option #2: Use an existing HTML template

If you’re not a graphic designer but need to send your newsletter quickly, use a pre-designed HTML template. When creating an email in Autopilot, you can choose from one of our responsive email templates:

Some of the HTML email templates Autopilot customers can choose from.
Source: Autopilot
autopilot html email templates

If none of those fit the bill, you can find an Autopilot-compatible template from one of our recommended email editors or select one of 600 free email templates and template builders.

Option #3: Design an HTML template from scratch

If you have the time and resources, work with a designer to create a custom HTML template.

Not sure where to start? We recommend compiling or authoring the content that will be included in your first email newsletter before choosing a design to match. This will help determine the number of sections you’ll need, copy placement, and image sizes.

Another key consideration—and one of the great marketing debates—is whether you should go with a single- or two-column email newsletter.

Two-column newsletters are easier to digest, but single-column newsletters get more clicks.

You have your classic two-column newsletter lovers, who tout the scannability benefits of a more compact view. Not only can you pack in more content using less space, but there are more opportunities to showcase that content above the inbox fold.

On the other hand, single-column newsletters are more responsive, meaning they easily adjust to different screen sizes. They are also flexible, attractive, and have a lower chance of breaking—regardless of whether you choose to include three sections or ten.

After testing single- versus two-column newsletters at Autopilot, we concluded that two-column newsletters are easier to digest, but single-column newsletters get more clicks.

Here’s an example of the layouts, side by side:

A side-by-side example of one- and two-column newsletters.
Source: Autopilot
autopilot html email templates

While two-column newsletters had fewer overall clicks, distribution of the clicks was more evenly spread, regardless of how the content was ordered. In other words, bottom-left corner sections were clicked on just as often as those in the first row. While the single-column variation had higher click volumes, these were all concentrated in the first few sections, meaning links near the bottom didn’t get as much love. 

Optimize newsletter engagement

After you’ve chosen whether to send a plain-text or HTML email newsletter, follow these best practices, tips, and takeaways to optimize your newsletter engagement:

  • Start with your biggest announcement. The most clicked links are those positioned at the top. Make your copy and visuals attractive, timely, and actionable.
  • Don’t overload your newsletter with text. Readers scan emails quickly—often on their mobile devices—searching for interesting links and/or valuable learnings. Make it easy for them to click by creating visual hierarchy, using white space, font sizes, and colors to rank the importance of headers, body copy, and calls to action.
  • Attract your reader’s eye with visuals. If you’re sending an HTML email, visually represent each section with a graphic or illustration. Don’t forget to use cohesive images, balanced proportions, and on-brand color palettes.
  • Write punchy headers. Structure your newsletter for the skimmer. Most will not read the four to five lines of subtext, so keep your headers short and relevant.
  • Make it personal. People want to hear from people. Match a recognizable human face to your brand by sending your email from a real person, like your founder, CEO, or other spokesperson. In our tests, newsletters sent from our CMO converted 12% better than a generic company sender like “Your mates at Autopilot.”
  • Be social. Encourage readers to follow your brand, share your content, and join conversations on Facebook, Twitter, LinkedIn, and other active social channels. You should also include links to your Help Center, offer ways people can get in touch with your support team, or encourage your audience to leave a positive review.
  • Send a 48-hour follow-up email [Secret weapon]. Sometimes subscribers who want to hear from you simply miss your first send. Maybe they were busy, traveling, or just didn’t have time to open your newsletter that day. You can double your newsletter open rates by sending a second copy 48 hours later to those who didn’t open the first email with one small modification to the subject line: “Reminder: <original subject line>”. This simple tactic will increase your open rates without significantly increasing your unsubscribe rates. (We templatized this technique in our “Advanced Newsletter” journey, which is available in the Autopilot Guide BookThat means you can try it for yourself in a single click. Score!)
People want to hear from people. Match a recognizable human face to your brand by sending your email from a real person

Measure newsletter performance

Most email or marketing automation software offers basic reporting on email performance. While rough industry benchmarks exist, newsletter performance varies by industry, customer demographic, geography, and business model.

We recommend tracking the following:

  • Total number of contacts: Every member of your marketing team should know both the size of your database and how many of these contacts receive your newsletter. Set quarterly or annual goals for growth, and incentivise newsletter signups by placing a benefits-driven sentence alongside the lead capture form on your website or blog.
  • Open rate: You should be achieving 10-20% newsletter open rates when sending to your entire marketing database, and higher if you are targeting specific segments.
  • Click-through rate: Typically, 3-8% of people who open your newsletter will click. However, highly relevant messages backed by compelling offers can drive your click rates up to 50% or more.
  • Unsubscribe rate: If you have a groomed reader base (i.e. you’ve sent four or more monthly newsletters to the same list) and are seeing unsubscribe rates that are higher than 0.3% after each newsletter send, consider revisiting your targeting strategy, content strategy, or send frequency.
  • Attributed MQLs, paying customers, and upsells: How many leads or conversions are your newsletters producing? Add UTM tags to your email URLs using Google or a similar UTM builder like Effin Amazing, then track on a cohort basis in Google Analytics or other attribution tool.
  • Engagement and feedback: How are people responding to and engaging with your newsletters? Gather qualitative feedback by encouraging readers to reply to your emails or embedding a survey link. You can also track social shares on key content before and after sending your newsletter. 

Highly relevant messages backed by compelling offers can drive your click rates up to 50% or more

Send a newsletter with Autopilot

When creating a journey in Autopilot, you can either build it from scratch or use a best practice template from our Guide Book.

autopilots newsletter journey
Autopilot's newsletter journey

Regardless of the option you choose, sending a newsletter with Autopilot couldn’t be easier. Simply drag, drop, configure, and publish.

1. Choose your contacts

Before structuring your journey, you’ll need to build your newsletter recipient list. Here’s a few ways to do it:

Option 1. Send your newsletter to all existing contacts. This is by far the easiest option, but comes with some obvious flaws. Configuring your list trigger is easy. All you need to do is click on the trigger and select “all contacts”.

Option 2. Create a list of contacts who you want to receive your newsletter. To do so, either import a list of contacts or set up a Zap that imports them automatically. If you choose to import a list of contacts, remember to regularly update the list to include leads that have signed up for your newsletter.

Keep in mind: If you use a list trigger, contacts will receive your newsletter as soon as you publish your journey. You can also use a time trigger, which enables you to schedule your newsletter for a future date and time.

Option 3. Switch out the list trigger for a smart segment trigger. This tool allows you to build a list based on the criteria you specify. For example, you could include only current customers.

Once you’ve set up your smart segment list, add a smart segment trigger to the canvas of your newsletter journey. To configure this trigger, simply click, search for and select your list, and choose one of the three options below.

2. Structure your journey

Once you’ve built your list of newsletter recipients, it’s time to structure your journey.

Step 1. Add your newsletter  

Drag and drop the send email shape onto your canvas and connect it to your trigger using the connection arrow.

When you click to configure this shape, you’ll be presented with three options:

  • Select an existing email (not recommended for email newsletters)
  • Select “new email” to create your newsletter from scratch
  • Select “manage existing” to duplicate and edit an existing email

Regardless of the option you choose, we recommend crafting your message after you’ve finished structuring your journey.

Step 2. Check your email status (with a short delay)

Next, add a check email status condition with a small delay (e.g. 48 hours). This will enable you to route subscribers based on whether they’ve engaged with your newsletter.

Step 3. Add your newsletter reminder

Finally, send a friendly reminder to subscribers who haven’t yet had a chance to open your newsletter.

After structuring your journey, it’s time to craft your newsletter and newsletter follow up messages and configure your email.

3. Craft your messages

When creating a new email, you’ll have the option to start from a blank HTML template, upload your own HTML template, or make use of one of Autopilot’s templates.

Pro tip: If you’re going to upload your own template into Autopilot, we recommend adding editable tags to your template so that you can edit it in Autopilot before publishing your journey. See here for step-by-step instructions on how to add editable tags to your HTML templates.

In this example, we’ll use Autopilot’s newsletter template. Once you’ve chosen the template, you have the ability to fully customize the images and copy. While doing so, don’t forget to leverage personalization variables (complete with fallback options), customize the unsubscribe link, and add list-specific subscribe and unsubscribe links.

If you’re looking for some newsletter inspiration, check out Autopilot’s new newsletter, which is based on 12 months of a/b testing:

Now that you’ve polished your newsletter, the final step is to review, test, and publish your journey.

4. Review, test, and publish

When you’re happy with your emails, send yourself tests to ensure the formatting looks correct on both desktop and mobile. Don’t forget to click on all links to ensure they’re working. Once you’re confident, send the same tests to one or more colleagues. A second (or third) pair of eyes never hurt anyone!

Note: If you’re going to use a lot of custom HTML, we recommend using a testing platform such as Litmus to test across browsers and devices before publishing.

Finally, publish your journey. If you used a list trigger, your newsletter will send right away. If you used a time trigger, the journey will fire at the date and time you specified. Congratulations!

Going forward, keep in mind that this journey can be used as a template for future newsletter sends. Simply duplicate the journey, update your trigger (if required), and duplicate your previous email by selecting “manage emails” from the send email shape. Good luck!

Further resources

Want to learn more about email newsletters? Check out these helpful resources:

Next Lesson

Lesson 2: Turn 1-Time Buyers into Loyal Customers

Repeat buyers deliver the same revenue as five new customers combined and are nine times more likely to convert. Repeat buyers make up just 8% of visitors, but deliver a ...

Go to next lesson