How Grammarly sends onboarding email

Weekly digests and lots and lots of ways to upgrade

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What do those new users experience when they join the product? To find out, I started a free Grammarly account to see what the onboarding emails are like (no surprise, they’re impeccably spelled and punctuated). Here is what I received this fall after I signed up.

Total: 10 emails sent, counting the email confirmation.

There seemed to be an interesting mix of strategies in Grammarly’s first few emails. Or maybe I just signed up during a particularly communicative season of life.

First, there was the primary drip campaign with a pair of onboarding emails. The first email, sent on Day One, was about logging in to my Grammarly editor and getting started. The second, sent on Day Two, was about installing the native Mac app and browser extension.

However, also on Day One, I received an email to … install the browser extension. I later realized after looking at the UTMs in the email that it was triggered by me: I hadn’t completed the process of downloading the extension. So essentially it was an abandoned cart email (the UTM campaign was “”AbandonedExtension”).

Then after these initial emails, I appeared to be pulled into a three-email upgrade campaign: 1) Upgrade to Premium, 2) 40% off an upgrade to Premium for the next 2 days, and 3) The 2 days are almost up!

After this, though, things got a bit clearer. It appears that Grammarly places you onto a weekly digest email after your initial two weeks, then every Friday or Saturday you receive a digest of your Grammarly stats from the past week. It’s an awesome retention idea and one that I think just about every app should try some way, somehow.

Here’s more on each email that I received from Grammarly during my first 35 days.

Sent minutes after I signed up.

Subject: You + Grammarly = The Dynamic Duo
From: Grammarly, info@send.grammarly.com

Sent the same day after I signed up.

Subject: You’re Missing the Best Part of Grammarly
From: Grammarly, info@send.grammarly.com

Sent the day after after I signed up.

Subject: Get the Most Out of Your Free Account
From: Grammarly, info@send.grammarly.com

Sent five days after after I signed up.

Subject: Upgrade to Grammarly Premium, Become a Stronger Writer
From: Grammarly, info@send.grammarly.com

Sent seven days after I signed up.

Subject: Write Like a Pro. Here’s 40% Off Grammarly Premium!
From: Grammarly Premium, info@send.grammarly.com

Sent nine days after I signed up.

Subject: Last Chance: 40% Off a Grammarly Premium Upgrade
From: Grammarly Premium, info@send.grammarly.com

Sent 11, 19, and 25 days after I signed up.

Subject: Your Weekly Progress Report
From: Grammarly Insights, info@send.grammarly.com

Maybe I just happened to sign up during an especially high time for upgrade prompts, but it seems like Grammarly sends them all the time. A couple weeks after my first 35 days with the product, I got one with the subject line: CELEBRATE! We’re giving away Annual Plans at 45% OFF 🎉

If you have some thoughts or questions about Grammarly’s onboarding flow, I’d love to hear them.

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Want to see more onboarding email breakdowns? Check out the rest of Season One of the series, featuring onboarding campaigns from …

👉 👉 Intercom ……. Trello ……. Extra.ai ……. Brandless ……. Fullstory ……. Wistia ……. MixMax ……. Grammarly ……. Dribbble ……. Hubspot ……. Pocket ……. Treehouse ……. CBS All Access…….

All available now on Medium.

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