The 5 email sequences you need to earn more paying subscribers

You’ve got to sell your paid subscription tiers.

But it’s exhausting to promote them manually every week. When do you send a standalone email? How much should you lean on social media?

Enter automated sequences.

Automated sequences are emails that send in the background based on when your reader does something. I’m noticing they are heavily underutilized by journalists (us marketers are lighting up inboxes with ‘em!)

So today’s issue is the 5 sequences you should consider adding for your publication.

P.S. Welcome if you’re new to hearing from me! I try to get this newsletter out every Saturday morning (New York time) but I’ve been away on vacation. Glad you’re here :)

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5 email sequences you need to get and keep more paying subscribers

1️⃣ Welcome sequence for free readers

Welcome sequences ensure readers know their way around your publication. If you have different columns or various types of newsletters you send, you can use the welcome sequence to get them building a habit of checking for those. You can make a paid upgrade offer here too, but I wouldn’t hard sell it just yet.

Timing: Right after reader joins newsletter
Purpose: Get them familiar with your publication and help them build a habit around reading it
Include: 1-5 emails on what to expect, where to keep up with your work (web, email, social), about you and your team, why your publication exists, your coverage areas or recent notable coverage, etc
References: Inbox Collective on 6 types of welcome emails and email marketer Liz Wilcox on what makes a good welcome sequence

2️⃣ Welcome sequence for paid readers

Your current paying subscribers are the most likely to keep paying you and refer their friends. A welcome sequence for paid readers can re-emphasize some of the same things as the free welcome sequence AND it should cover how to access member perks and how to spread the word about their new membership.

Timing: Right after a reader upgrades to paid
Purpose: Create paid subscriber loyalty, increase utilization of their subscription and tee up referrals
Include: 1-5 emails thanking them for their support, showing them how to use subscriber perks, how to access RSS/podcasts/newsletters/events/special areas, encouraging them to forward emails or shout out on social that they just joined (Recommend using a Senja link to capture it also as a testimonial)←affiliate link because I’m a huge fan of Senja
References: Email Marketing Heroes on member onboarding and Membership Geeks on how to onboard

3️⃣ ‘Why pay’ sequence for free readers

This is something I coined for a newsroom marketing test, but in other industries, it’s referred to as a promo, sales or upgrade sequence. A “Why pay” sequence is exactly what it sounds like—you tell your reader why they might want to pay for your publication. What’s in it for them?

Timing: 6-8 weeks after they join your newsletter for free (or set this to your most likely upgrade timeframe)*
Purpose: Get your reader focused on your subscription options (more than you can within a regular newsletter) and sell them on it
Include: 3-5 emails about your vision, subscription options, subscription perks, and what other subscribers say made them upgrade. Pull on a different motivator with each email (hint: use your reader surveys to learn these!)
References: This issue I wrote about 404 Media’s version of this, Beehiiv on writing conversion copy for sequences and ConvertKit on effective product launch emails (different use case but relevant recommendations)

4️⃣ Abandoned cart sequence

If someone put their email address in when they started buying a subscription but they leave before they finish the transaction, you can send an abandoned cart email or two. Chris Nguyen, a digital product creator, turned this feature on for his website and told me that 9% of the people who got the email converted into paying customers.

Timing: 24 hours after the subscription was “added to cart”
Purpose: Remind your reader they were buying a subscription and see if they still want to. People get distracted!
Include: 1-2 emails asking if they want to continue getting a subscription. You can reuse parts of your Why Pay sequence or you could add a secret discount code here to encourage them to act fast. (That’s what Chris did)
References: Copyhackers on the best abandoned cart emails and 12 examples of abandoned cart emails

5️⃣ Churn prevention sequence for paid readers

It is not a given that readers who pay will keep paying. In fact, churn is the biggest culprit for revenue decline in most subscription businesses. It’s easier and cheaper to win back or keep a paying reader than it is to acquire a new one. And very few businesses handle this well. Your subscribers will appreciate your efforts!

Timing: The timing here will be specific to your publication but an example could be 6 months into a monthly subscription or 11 months into an annual subscription
Purpose: Remind your reader why they became a subscriber, what they get and why they should keep it going. Enlist them in your endeavors and show them a little behind the scenes on subscriber goals and what they enable for your publication.
Include: 2-5 emails celebrating their support, updating them on what’s changed/notable coverage, reminding them about perks, highlighting goals achieved/upcoming and motivating them to stick around.
References: Mailmunch on email strategies that reduce churn and Paddle on prioritizing the right churn strategy

*6-8 weeks is based on a newsroom I worked with in the spring. I analyzed their data and found this was the most likely upgrade time. You can do the same when you compare your newsletter join → upgrade dates in your newsletter tool.

Our takeaway

You can start tapping into your reader’s mindset and getting on their timeline right when they first make themselves known to you.

Using automated sequences can ensure your publication is selling itself, even when you or your team don’t have bandwidth to promote your subscriptions. You will also ensure your paying subscribers feel taken care of and acknowledged for their support.

Choose one to start (recommend the Why pay sequence) and let me know how it goes. I’d love to hear what works for you!