A re-engagement email and win-backs help your newsletter avoid spam traps

person reclining in a park

We know that a trustworthy newsletter makes it easy for people to unsubscribe. But what about the people on your list who have ghosted your newsletter? That’s why you need a re-engagement email.

Some subscribers engaged for a bit, but they haven’t opened, read or clicked a single email in weeks. Or months. If you’re thinking “or years”, this post is definitely for you.

What percentage of your list hasn’t opened an email in 9 months or longer? 5%? 25%? Be honest, it’s okay.

You will lose 20-30% of your list every year. People get cluttered inboxes. They move out of your area. They only wanted a special offer. Their circumstances change. It’s a fact of life.

Inbox providers like Gmail, Yahoo or Outlook keep tabs on inactive inboxes. Let’s say someone hasn’t logged into their email for two years.

When you send your newsletter to this inactive email address, it shows inbox providers you don’t keep a clean mailing list.

You know who else doesn’t keep clean mailing lists? Spammers.

That’s a major problem. If you don’t take list hygiene seriously, it’s going to screw your deliverability big time. If your email provider charges you based on your number of subscribers, then your list is costing you more for worse performance.

I have good news though. You don’t have to scrub every inactive subscriber off today. We’re gonna win some subscribers back.

The re-engagement email

The re-engagement email is exactly what it says on the tin. It’s a very brief email you send to your dormant subscribers to make sure they are still there, and keep you on their radar.

Quick note: In this post, I also use the term win-back email. A win-back email is similar to a re-engagement email, with slight differences.

Ideally, you will send 2-3 re-engagement emails. After all, if a subscriber hasn’t ignored you for 6 months, there’s a pretty minimal chance they will jump at your first attempt.

But again, I have good news. In a study by Return Path, 45% of subscribers who received win-back messages read subsequent emails (PDF link). Here’s the kicker: only 24% of those people read the win-back email.

That’s bananas! In this study, people who didn’t even read the win-back email started opening emails again.

I need to manage your expectations here. The re-engagement email isn’t going to jumpstart all your inactive subscribers. Chances are, the open rate on the re-engagement email is going to be lower than your list average — and that’s okay.

The value is retaining subscribers who lapsed but are still interested. Retention is incredibly important for building loyal audiences. Depending on whom you ask, a new customer costs 5x-25x to get versus keeping an existing customer.

In a world relying more on reader revenue and paid subscriptions, retention can’t be a secondary goal. Subscriber churn devours startups before they even know what hit them. Churn bogs down an established newsroom like quicksand — the more you fight the deeper you sink.

Before you write your re-engagement email, define what inactive means.

There is no one-size-fits-all re-engagement email formula. Defining your goals and your terms is the most important place to start. You have to do this first.

Your approach changes based on what your newsletter’s goals are, and the frequency. Without these two pieces, you can’t define “inactive”.

For example, if your newsletter is designed to drive revenue, “inactive” should tie to the last order or donation. Keep in mind that higher orders have a longer lead time than small orders.

On the other hand, newsletters driving clicks to your site should use indicators like the last time they opened or clicked an email.

Newsletter frequency needs to be considered in your “inactive” definition. Let’s say Newsletter A goes out every day, and Newsletter B sends once a month. If a subscriber is inactive for 9 months, that’s 273 emails of Newsletter A, but only 9 emails of Newsletter B.

It’s easy to think “oh, they haven’t responded for 9 months, so we’ve lost them”.

It’s important to follow up and talk to inactive subscribers. People may have good reasons why they aren’t engaging, and they may reveal opportunities you weren’t seeing.

Pick one action. Only one.

Your goal with a win-back is to figure out if this subscriber is still on the other end of the line. That’s it.

There are only three ways this will go: Yes, No and Silence.

To capture the Yes people, give them a nice big “Yes, I still want to get your emails” button. For the no people, don’t ask them to manage their preferences. Make it easy for them unsubscribe, or better yet, let them know you will take care of it.

If you have multiple newsletters, give them an opportunity to change the frequency. You make keep some by letting them change from daily to weekly.

Truthfully, most of these inactive subscribers will fall into the Silence category. What’s next for them?

For starters, keep that Return Path study in mind. There are some people who don’t open or engage with the win-back email who will start opening emails again. Think of them as a delayed “yes”. These count toward your success!

Timing is important; don’t jump the gun

As a general rule, inbox providers consider an address inactive if the owner hasn’t logged in for 12 months. After that 12 months, each email you send risks getting you on their spam radar.

But there’s another part of the Return Path report that is interesting. The average time it took from win-back email to reading a later email was 57 days. Almost two months!

Give yourself a buffer between sending your re-engagement email and scrubbing your list. As long as you don’t zoom too far past the 12 month marker, you may pick up a few more hibernating subscribers.

During that buffer period, you should send more than one re-engagement email. I suggest 2-3. They aren’t opening your emails, so you probably aren’t going to get their attention in one shot.

What does this look like? With a daily newsletter, 6 months of unopened emails is probably plenty. Send them a win-back after 5 months, then again at month 7 and a couple weeks after that. If they still haven’t opened anything by month 9, scrub them.

That’s not super aggressive, and it’s manageable. Your results may vary, and you should test this. In fact, as you establish good list hygeine, you may find you benefit from a shorter or longer schedule.

Avoid the urge to be a comedian

One of the hottest — and stupidest — trends today is the use of needy patterns. You’ve seen them as links under call-to-action buttons, usually something like “No, I hate saving money” or “No thanks, I don’t like to learn things”.

"I'd look like a real jerk if I said 'No'"

Even if these get more conversions, they are not worth it. They are rude and unnecessary. Building loyalty is a long-term game, and needy patterns are cheap shortcuts.

A lot of win-back emails from retailers take on a tone of of a break-up. That may work for retailers, but it’s often comes across as silly. Be straightforward and user-focused.

What should your re-engagement email say?

This is normally where I share examples from the 99 Newsletters. I’m opening and re-opening and clicking on emails in the 99 Newsletters, so I don’t have any win-back emails to share.

So we have to improvise a bit with a re-engagement email from James Clear, author of Atomic Habits.

This one came on a super short lead time — about a month after I signed up. I guess James likes to keep a sparkling clean list!

James does three things in this email that I really like:

  1. He is respectful of your time and your inbox, in those words. “I want to make sure I’m not wasting your time by sending you emails you don’t want.”
  2. One action for the reader. If you want to keep getting emails, click the one link in the email. It’s even in bold. I like buttons better, but this is great.
  3. If you don’t want more emails, you don’t have to do anything. You’ll automatically be removed. Not your problem to solve.

I don’t even think you need to say this much, especially the paragraph about the email software. Most likely your subscribers know they ghosted, or they are using your newsletter for other purposes.

For your email, this is a great opportunity to mention any big improvements you’ve made. Maybe you unveiled a more user-friendly design, or got rid of autoplaying video ads everyone hates. If you fixed something, don’t feel you need to hide it. Being honest about what you fixed may overcome their reluctance to come back.

You could also mention a big new initiative that’s gaining traction, or an award winning story.

But you can only pick one thing.

One thing. Seriously. If they haven’t read the last 273 newsletters, they for damn sure aren’t reading your list of 273 things you think they missed.

Be careful offering discounts as bait

There are only two ways to increase revenue:

  1. Sell to more customers
  2. Sell more units to your existing customers

Subscription businesses without tiers must do Option 1: find more people to buy subscriptions. It doesn’t do most people any good to have four subscriptions to the same news site.

Retailers often use coupons or discount codes to win back customers who haven’t ordered in a while. That works for retailers, but it can be an uphill road for publishers.

Why is it an uphill road? For starters, it conditions people to wait for the deepest discount. They take the good offer, and they are more likely to cancel at the end of the cheap rate. It creates a vicious cycle when budgets are tight enough.

It also comes across as desperate. In the past month, the New York Times has sent me ten “special offers” to subscribe. TEN. That’s one every three days. One one day, they sent me two offers less than 12 hours apart. The same day!

I didn’t open any of them until I started researching this post, because I’m not interested. When I counted up all the offers – I was less interested. And the sheer repetitiveness shows these offers aren’t special at all. They are just cheap.

Don’t copy the New York Times. This is not how you do win-back emails.

Segmentation makes re-engagement more effective

Re-engagement and win-backs get a huge boost from segmented lists. People lose interest for different reasons, so they aren’t going to be re-engaged for the same reason.

An up-to-date segmented list gives you flexibility. Segments position your win-back around your readers’ interests or previous purchases.

Segmentation doesn’t have to be complicated or technical, either. Start small and work your way up.

What if you segmented your list by paying subscribers, former subscribers and non-subscribers? Each group has a different relationship with you. Approach them in the appropriate context.

Disengaged paying subscribers may love a discount offer. Offering a non-subscriber a steep discount could lead to high turnover, short-term subscribers. High churn costs you more in the long run.

The key is testing small batches as much as you can to figure out what works. Confirm your findings, review your strategy regularly and keep doing what works.

I know a lot of newsletters aren’t segmenting lists, probably because they aren’t sure where to start. I’m not here to shame. If getting started with segmentation has been on your radar, shoot me an email and we can talk about getting you up and running.


Photo by Ilham Rahmansyah on Unsplash

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Cory Brown

Cory Brown

I help newsrooms develop email and subscriber strategies so they can reduce churn, grow revenue and build a sustainable future.

I don’t growth hack. I build.

I don’t want to disrupt. I want to have impact.

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