3 Win-back emails you shouldn't copy

Hey hey,

David here, from Send Good Emails.

Email automation is powerful. It saves time and brings in results. But here’s the thing: lazy automations backfire. They feel cold, impersonal, and often end up pushing subscribers away—the exact opposite of what a win-back email should do.

Today, I wanted to share 3 examples of win-back emails I recently collected for Send Good Emails. Our database now has 94 email sequences from 78 companies (319 emails in total) because knowing what works is as important as knowing what doesn’t work.

Let’s break down the specific emails:

Grammarly

After canceling my $100/year subscription, Grammarly sent a quick email with the tagline “Goodbyes are hard.” Good start. I like it.

The next section confirms cancellation and says I wouldn’t be billed again. Positive but a bit of a weird follow-up.

And then… nothing.

No benefits of staying, no highlights of features I might not know about, no testimonials. Nothing that makes me rethink my decision.

How to do it better: Reinforce why users loved the product in the first place. Show the benefits of sticking around. A little nudge with features I’d miss out on or a client testimonial could’ve made me reconsider.

Substack

Context: I clicked on an offer, got redirected to the app download, and dropped off there.

Substack then sent two follow-up emails that were just… cold reminders. I get it—they don’t know much about me. But the email doesn’t address why I might not have completed the process.

How to do it better: Start by addressing the likely friction point—the app download—and why it’s worth it. And use what they know about me (that I read newsletters) to highlight how the app could improve my reading experience. Maybe even tie it to the specific newsletter I enjoy—personalize it to show what I’m missing out on.

Google

This one’s different, and honestly, it’s the best example of the bunch.

Sent after 90 days of inactivity, Google’s email encourages users to contribute to their platform, gamifying the experience by offering points for various actions.

Here’s what they got right: they emphasize giving back to the community and show which actions get the highest points, guiding users to actions that matter.

How to do it better: Display users’ current points and their next milestone. A small rewards system could further incentivize engagement.

The takeaway? 

Win-back emails need to show effort. If your subscribers sense the email was thrown together without thought, they’ll know. Invest in a few more personalized touches, emphasize benefits, and remind people why they loved you in the first place.

Catch you in the inbox,

David
Send Good Emails