The Five Types of Automations

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In today’s email landscape, I think there are two types of senders: There are people who approach through the lens of newsletters, and those who approach it through the perspective of marketing.

People who read Inbox Collective mostly live in that newsletter world. If you’re reading this, there’s a good chance you work at a newsroom or a non-profit, or maybe you’re an independent newsletter operator. People in the newsletter world are really smart at thinking about how to use email as a tool to build relationships and drive specific actions. Maybe you want your audience to read stories about what’s happening in your community, or want to teach them something new, or want to share new ideas with them. But you start with newsletters, and then layer the monetization piece on top of that. You could be selling ads, selling books or products, nudging people towards paid services, driving a subscription, membership, or donation — however you make money, that’s something that’s built on top of your regular newsletter strategy.

Then there’s the marketing world. These are people who work at ecommerce companies or large businesses, and they look at the inbox differently. A lot of these companies are, of course, thinking about long-term relationships — they want their audience to be customers for a long time. But most of the focus is usually on one key metric: Sales. Engagement metrics like opens, clicks, or unsubscribes are all viewed in service of the larger revenue strategy.

As more people in the newsletter world think about monetizing their email audience, I think there is so much that we can learn from these marketers. (People in marketing could certainly learn a lot from newsletters about how to build relationships, but we’ll save that for another post.) When I look at the marketing world, I see teams deploying sophisticated automations to engage readers at specific moments — and then selling them stuff that matters at that moment. There are five key automations that just about everyone should have set up as part of their larger email strategy.

Building out a smart automation strategy can unlock huge amounts of revenue for any newsletter or newsletter-first business. Here’s what you can learn from best-in-class marketers to turn those readers into loyal, paying supporters and customers.

Understanding the customer lifecycle

There’s a phrase that many marketers like to use when they talk about their paying supporters: Customer lifecycle. When I think about a customer’s lifecycle, I like to imagine a journey for each of my readers. On one end is a reader who doesn’t know anything about me or my brand. On the other end is a loyal, repeat supporter. (I’m going to use the word “supporter” from here on out, but know that by supporter, I mean any paying subscriber, member, donor, or customer.) The lifecycle represents all the steps along the way that move readers from one place to another — and there are potentially a lot of steps along that journey.

How do you move readers from one step to another? Your newsletter certainly has a key role in driving engagement, but there’s a powerful tool at your disposal, too: Automations. These are pre-built emails that are triggered by specific actions and designed to nudge readers to that next step.

In a perfect world, you’d have five different types of automations aimed at five key moments in that reader’s lifecycle.

• Have a new email subscriber? You can greet them with a welcome series.
• Didn’t get that reader to support your work? You can nudge them with an abandoned cart series to get them to pay.
• Have a new paying supporter? Use a post-purchase series to get them to engage more deeply with you.
• Need to drive another payment? Use a refill, upsell, or renewal series to get readers to pull out their credit card and pay.
• Lost a supporter? Use a winback series to get them to come back. 

So let’s talk about each of these types of automations, first by sharing what pros in the marketing world are doing, and then explaining how you can adapt the tactic for your newsletter.

Welcome emails

When it comes to email, first impressions are everything. Get someone to engage early on and you have the chance to build a relationship with them for a long time. But the inverse is also true: If you don’t grab their attention right away, you may never get the chance again.

That’s why a welcome series is so important. It’s your chance to drive early engagement that can lead to long-term relationships and long-term revenue. What I see from the marketing world is that businesses are often offering some sort of incentive, like a discount code, to encourage people to hand over their email address and get them onto the email list. So with these welcome emails, their goal is pretty straightforward:

1. Deliver your promised incentive.
2. Set the tone and expectations for future emails.

Scott Cohen, CEO of InboxArmy, reminds his marketing clients that these emails are particularly important for any brand that doesn’t send out a daily email. “If I sign up today and you don’t send me anything, and your next email is a week from now,” he said, “there’s a six or seven-day gap where your reader is going, ‘Do they even know I’m here?’” These welcome emails close those potential gaps in your communication strategy.

In the newsletter world, I think teams need to take things even further with their welcome series — a single welcome email isn’t enough. I’d encourage you to think about sending at least three to five welcome emails in the first 30 days after someone signs up. 

Start by putting together a list of the things you absolutely want your reader to do in those first 30 days. That might include:

• Getting them to reply to you.
• Introducing yourself or your team.
• Telling them about your mission.
• Sharing some of your best work.
• Nudging them to take a next step like, signing up for more newsletters, downloading your app, subscribing to your podcast, following you on social media.
• Learning more about your readers and their interests. 
• Asking them to support your work. 

Each email in the series might focus on one of these bullet points. I’ve got examples here with more detail on how to incorporate these action items into each email.

The Six Types of Welcome Emails

But I do want to go into more detail on the final two bullet points, because they’re a huge opportunity for any newsletter. 

The first is to use the welcome series to ask your readers questions. An email address can be the first step to unlocking a lot of information about your readers.

• Demographic data — This might include a few questions, like: Where do you live? What do you do for work? Did you go to a university? Do you have kids?
• Behavioral data — With this, you’re asking: What types of content do you like to read or engage with?
• Psychographic data — These tie into a reader’s interests. Ask: What do you care about? What topics are you interested in?

Try including a survey early on in the welcome series to ask a few questions about your audience. Some of this data might help you build out the media kit that you share with potential advertisers. Some might help you improve the content that goes into the newsletter. And some can be used to personalize marketing emails later on.

Let’s say, for instance, that you’re a B2B newsletter that covers the construction industry, and you regularly host private meet-ups for people who own construction businesses. Getting an email address is good, but you’d want to also learn who owns a business and where they’re based. So you’d want to incorporate questions about job title and location into this survey. The key here: Only ask questions if you know how you’ll act on them.

There’s one more thing to think about: Driving readers to support your work. My rule is that every email in the series should include a call to action to pay, subscribe, become a member, or donate. In the first few welcome emails, you might have a sentence towards the bottom asking them to support your work, while the rest of the email focuses on another action item, like introducing yourself to your reader.

Later emails might include a more prominent call to action. But every email should have an ask — the reader might be ready to support your work on day 1 or day 30. Make sure it’s easy for them to take the next step whenever they’re ready.

Abandoned cart emails

An abandoned cart email is anything that goes out after someone starts to make a purchase but doesn’t complete the process. If you’ve ever started the process of buying a pair of jeans, stopped, and then gotten an email an hour later from that brand reminding you that there’s still time to buy those jeans, well, you’ve seen an abandoned cart email in action.

From a marketer’s perspective, the subscriber who makes it to the checkout page and doesn’t pay is like a marathon runner who runs the first 25 miles but with a mile to go. They’re so close to becoming a customer, and it’s your job to get them to that finish line.

Cohen pointed out one common reason why people don’t complete the process: Their credit card payment failed, and they didn’t try a second card. Cohen advises marketers to go through what he calls their RTBs, or “reasons to believe.” These are the brand’s talking points that explain why you should make that purchase.

For marketers, an abandoned cart series might have three parts:

• First, they’ll send an email reminding this user that they haven’t completed the purchase, and show them what’s in their cart.
• Second, maybe a few hours later, they’ll answer more questions about the product and try to overcome any objections the user may have that would keep them from paying.
• Third, a day later, they’ll offer this user an incentive to get them to purchase.

Cohen’s advice: Don’t rush into offering that discount. “Customers are smart. They know to wait,” he said. “They know, ‘‘If I wait an hour, I’ll probably get a discount.’ So if you’re okay with that, great. But if you want to preserve your profit margin, wait them out.”

Abandoned cart emails are something ecommerce brands do so effectively to drive sales, but I find that newsletter-first teams tend to ignore these emails. The reason, I think, is two-fold:

1.) Many teams don’t realize that they have a “cart.”

2.) Many teams don’t have the technology to link their cart and their email system, so even if someone goes to the cart and doesn’t make a purchase, they don’t know how to send the follow-up email.

But the thing is: If you have a checkout page, that’s a cart. And you don’t need fancy tech to connect the dots between that page and email. There are other ways to tackle this. For instance: Let’s say you’re sending out an email asking readers to support your work. Wait 48 hours after the email is sent, check to see who clicked on the link to your checkout page, and then see who didn’t complete the process. You can then trigger an abandoned cart series just to those readers.

As for what to email those users: Brainstorm a few reasons why someone might not have paid, and then craft a follow-up email refuting those reasons. I really like this example from South Africa’s Daily Maverick, which I first saw on The Audiencers’ blog. They put together an abandoned cart email in the form of an FAQ, explaining why someone should want to become a member.

And if that initial email doesn’t work? Wait a day or two, then offer them a discount.

Post-purchase emails

Much like with a welcome series, it’s worth mapping out the steps you want a new supporter to take in the days and weeks after their initial payment. Start by making a list, which might include:

• Thanking them.
• Making sure they get into the habit of reading your newsletter.
• Inviting them to attend events.
• Asking them to share more about themselves.
• Encouraging them to join your community.

Cohen would add one more to that list: Helping this supporter overcome buyer’s remorse. “Especially if you’re shipping something, the gap between when they order and when the product arrives at their home, people freak out,” he said. “They’re asking themselves, ‘What am I doing? Why did I spend this money?‘ This is the time to over communicate.” There’s a reason marketers send so many emails with each shipping update — they want you, the buyer, to get excited about your purchase and feel like you made a good decision to buy. They also use these emails to help their new customers understand how to use the product. 

These emails are equally important for publishers, non-profits, and independent newsletters. I like to do a few things with this automation.

As soon as someone supports your work, ask them to sign up for more newsletters or take another step to engage more deeply with you, like subscribing to your podcasts. The earlier you can create multiple touchpoints for these supporters to find your content, the better.

Once the email sequence starts, that’s where you can start checking off the list of action items for supporters to take. Thank them, introduce your team, drive them to read your work — or even combine all of these steps into a single email.

You may also want to think about cross-promotion across all of your channels. It’s great to have an email address, but getting them onto your app or a texting platform, like SMS or WhatsApp, can drive even deeper engagement. A reader might miss that day’s newsletter, but if they get a push alert from you or listen to a podcast from you, they’re still getting value from you that day.

Make sure you have multiple emails in this sequence. I’d recommend at least three emails in this post-purchase series, but I work with teams that will send more than a dozen emails spread out over the first 100 days after someone pays. The most important thing, though, is what you send in the first 30 days — that’s your chance to hook a reader and get them to engage for a long time.

Looking for even more ideas for post-purchase emails? I’ve got suggestions here.

17 Tactics to Engage New Paid Subscribers, Members, Donors, or Customers

Sending refill, upsell, or renewal emails

I’ve walked through two automations designed to get readers to support your work, and one aimed at the moments after someone chooses to support your work. The final two automations are all about getting your supporters to come back again and renew their support. Let’s start with a reminder or renewal sequence, and this automation is one that’s very different for marketers compared to newsletter-first teams.

You’ll note that I mentioned three different variants of these emails. Marketers tend to focus on two of these: 

• Refill emails are sent when it’s time for their customer to make another purchase. For instance, let’s say you wear contact lenses. You might get an automated email a few weeks before your supply of contacts is set to run out, reminding you that it’s time to buy more contacts.
• Renewal emails, on the other hand, are sent when you’ve got a purchase that is set to auto-renew, and you need to tell your supporter that your credit card will be charged soon.

Senders in the newsletter world don’t usually focus on refill emails, as they don’t always have a product that supporters need refilled. But two types of emails do matter to these types of senders: Upsell emails and renewal emails.

Both are big opportunities to drive revenue. I’ll start with Upsell emails. Let’s say you offer two tiers for membership — a more basic tier, at a lower price point, and a premium tier, and a higher price point. Your supporter joins at the basic tier. You’ve converted a reader into a supporter, which is fantastic. But what if you could convert them to your premium offering?

The same thing is true for anyone who focuses on donations as their reader revenue model. Getting someone to donate once is great, but you can use an Upsell email to encourage them to become a recurring supporter.

With an upsell email, focus on showing your supporter that there’s more value they can unlock by supporting your work in a bigger way. That might mean showing them the benefits that they’ll get when they pay at a higher tier. It could also mean telling them about the way their support will help you and your team do even better work.

You can absolutely send multiple emails in this automation. Just make sure you’ve set up checkpoints in the automation to see if a reader has followed through and purchased the higher tier or donated again. There’s no need to keep emailing them once they’ve taken that next step. Make sure they’re immediately moved out of this automation and into a post-purchase sequence.

The other automation is a Renewal email. This is one that, in many countries, you legally have to send — you cannot charge someone’s credit card again without telling them. But I find that in many cases, teams basically send a receipt to their supporters. That type of email fulfills the legal requirements, but doesn’t do anything to actually get supporters excited to support your work again.

What I’d encourage you to try is a multi-part series instead that piggybacks off the messaging of the post-purchase series. First, send them an email highlighting some of the best content you’ve published during the past few months. Second, encourage them to take a high-engagement step — attending an event, for instance. With these two emails, the goal is to remind them of the value that you are providing to supporters like them.

Lastly, send a thank you email a few days out before their renewal date. Make sure you do a few things in this email:

1. Use your voice and personality. Just because this is a transactional email doesn’t mean you have to make it feel transactional. The more your personality comes through, the better.
2. Thank them again for their support over the past year (or whatever time frame they’ve been supporting you for). Tell them that you can’t do this work with their support.
3. Remind them what they’re going to get when they renew their support.

Cohen pointed out an interesting thing: “Oftentimes, in the subscription world, people are afraid to send out reminders for anything. They worry: ‘What if my paying subscriber cancels?’” But these renewal emails can be incredibly valuable. By being transparent with your supporters and showing value, you have a chance to get them excited to renew their support instead of hoping that they’re already excited — or just hoping that they don’t notice that next credit card charge.

If you do see a significant number of supporters cancel at this stage of the game, that’s a sign that you haven’t done enough in the post-purchase stage. Review those emails and see if you can spot opportunities to edit or expand the series to drive more engagement early on.

Sending winback emails

No matter how good your automations are, you will lose some supporters along the way. When that happens, that’s where the winback series kicks in. It’s your chance to, as the name suggests, win back the supporters who canceled.

Marketers often lean into a few different messages in this series. One is to remind them about the things they’re missing out on now that they’ve canceled. They’ll remind them of the content or products that they could be getting but aren’t because they’re no longer a supporter. Another is to offer a special discount code to encourage them to come back and support you again.

I’d recommend similar tactics for just about anyone in the email space. When you start, make sure you create a cancellation survey so you can ask these people why they chose to cancel. For instance, for a local newsroom, I might ask a simple question — “Why did you decide to cancel your subscription?” — and then list a few choices:

• The cost of a subscription was too high.
• I wasn’t reading enough stories to justify the cost.
• I don’t like the content you’re publishing.
• I’ve moved to another city.
• I had issues logging in or accessing your content.
• Something else

For the last option, make sure there’s an open-ended field where people can enter their reason for cancellation.

These responses can be a gold mine, if you’re willing to dig a little bit. Yes, lots of people won’t fill out the responses, and some will give you unhelpful or even hurtful answers. But if you sort through all of these, you’ll be able to identify certain patterns. This is actually a really good use case for AI tools. Download a file with anonymized answers, upload them to your AI tool of choice, and ask it to identify key themes or quotes about why people canceled. There’s so much in there that can help you understand how to build a better product for your supporters.

What’s great is that you can then connect these responses to your winback series. Let’s say someone tells you the price point is too high. That should trigger a series of emails built around a reduced price offer to try to win them back — tie the emails directly to their answer. Or if someone has technical issues, you can reach out to them to try to fix the problem. Do that, and you may not even need to offer a discount to get them to return.

Keep in mind that there are plenty of reasons why people would never return to your content. For instance, if you’re a local newsroom in Boston and your supporter moves to Beijing, it may not matter how much they like your content. Your content or services may not be useful to them anymore, no matter how big a discount you offer them.

A few more best practices for these types of emails:

1.) Test out messages from your brand’s voice versus ones from specific people on your team. I’ve seen both strategies work, and you should try both types of emails to see which has the best conversion rate. 

2.) Try to reframe any features in terms of the value for the reader. For instance, telling a former paying supporter that you have an app is great, but it might be even better to remind them that only paying subscribers can receive breaking news alerts — sent via the app — to keep them more informed about what’s happening in their community. Don’t just tell them about the features — tell them why these features will benefit them.

3.) Make sure you target readers not just in this automation but also in your regular newsletters. Most email platforms allow you to set up some sort of in-newsletter message, shown only to certain types of readers based on their profile information. These readers are opening those newsletters anyway, so it’s one more place where you can get in front of them to say, “Hey, we miss you! Come back and give us another chance.”

Four best practices for these automations

There’s a lot to tackle here, but as you do, keep these rules in mind.

1.) Remember the three Rs — Those Rs: Review, rethink, and rebuild.

• First, review your existing automations. Ask yourself: Where is there room for improvement?
• Next, rethink the journey of a customer. What’s missing? Where can you add new touchpoints?
• Finally, start to rebuild your lifecycle journey. Pick one of these automations and focus on improving that. Remember that you don’t have to make all of these changes at once. It’s OK to do this piece by piece. Try to move things just a little bit forward in the next 30 days — even filling in a few gaps in your lifecycle can have a measurable impact on revenue.

2.) Keep asking yourself, “So what?” and “What’s next?” — As you write these emails, put yourself in the shoes of your reader and ask yourself: “So what?” You, as a newsletter or a brand, are asking the reader to take a specific action in each email. Is it clear why that reader should do so? Are you clearly explaining the value for them? Make sure you’ve laid out exactly why it’ll be so beneficial for them to take the action.

And after they’ve taken the action, ask, “What’s next?” That’ll help you figure out how to link the action to whatever the next email in the sequence needs to be.

3.) Make sure readers don’t end up in multiple automations at once — If a reader is in your welcome series and makes a purchase, don’t keep them in the welcome series. Remove them from that and put them into the post-purchase series. They’re going to be annoyed if they keep getting emails to encourage them to buy something after they’ve already bought some. Make sure your automation is set up so a reader can’t be multiple automations at the same time.

4.) Keep improving upon what you build — Check in on your automations on a regular basis — Cohen of InboxArmy recommends reviewing everything and making tweaks at least twice a year. Things break all the time in emails. I’ve seen teams find out that they’ve been sending out emails with broken links or major typos. Sometimes, teams realize months later that they’ve been sending emails from someone who no longer works at their company. Checking in regularly makes sure that you’re on top of any potential fixes.

Plus, checking in gives you the chance to keep improving things. You can fix that underperforming subject line or swap out old content for fresher stories. Whatever you build isn’t the final version of the automation — it’s just the next version.

Looking for even more examples of each of these five automations? Answer a few questions below and we’ll share the Holiday Automation Playbook, a free, 25-page guide with examples and opportunities to help you drive more engagement and sales this holiday season.

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