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What we learned from all of Grammarly’s marketing emails

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Check out our email marketing crush, Grammarly, everyone’s favorite grammar checker and writing improvement tool. Read this detailed email teardown.

A marketing crush. Do you have one?

We have several, and Grammarly, everyone’s favourite grammar checker and writing improvement tool, is definitely one of them.

We’ve been lurking on their emails for a few months now, and finally, we thought why not share this obsession?

The tool has over 20 million users, so we can’t be the only ones to have noticed their excellent usage of product analytics and gamification in their emails. As one of the most successful uses of AI, it’s no surprise that their marketing emails feel super high tech and elevated compared to just about any other brand.

What we’re spying on in this teardown:

  • Grammarly’s overall email marketing strategy
  • Welcome & upgrade email sequence
  • Insights emails
  • Churn-reducing email
  • Continued Premium upgrade offers
  • Email timing
what Grammarly does really well

We’re about to show a lot of emails (really long HTML emails by the way), and you might be wondering if you should stay put and check them all out.

We believe there’s plenty of things to learn from Grammarly. These are a few of things that Grammarly is doing exceptionally well:

  • Consistent follow up for their Premium upgrade
  • Continued onboarding and stickiness improvements
  • Using product stats in emails
  • Building a consistent, enjoyable brand
  • Adding value with content for writing lovers
  • Takes new users through a well-timed customer journey

We’ll be covering these lessons throughout our exploration of their email automations below, so stay tuned to see what these things look like in the wild.

Grammarly's email marketing strategy

Before we dive into all of the email examples, let’s start by taking a peek at their overall email marketing strategy to provide some context to what you’re about to see.

In terms of strategy, this is what is guiding their email content:

  • Onboarding sequence – They give new users what they need to get started and introduce them to the tool and the world of Grammarly.
  • Upgrade offers – They immediately transition from onboarding to upgrading, and they don’t stop sending these emails until the user has upgraded.
  • Insights emails – Every week, users receive an email with their usage statistics and content below that.
  • Churn & troubleshooting – If something goes wrong, and the user is no longer tracking activity, Grammarly is on top of it.
  • Brand building and value adds – They continue to share new content and features to bring users deeper into their world and deepen the relationship.
  • Gamify onboarding and loyalty – Grammarly takes a high tech approach to onboarding and relationship building by gamifying the entire experience and helping users “unlock” levels, rewards, and coupons.

Now, let’s look at Grammarly’s emails.

Welcome sequence for email

First up, we’ll start with their welcome sequence. When a user signs up, they get two welcome emails with the goal of getting them onboarded to the product. And then after that, they continue to receive emails about upgrading to Grammarly Premium.

The welcome emails

The very first email that a new user receives from Grammarly is super long (like almost all of their emails). But you know what? We’re here for it. Everything that’s in the email is there for a reason.

Grammarly's best emails

The purpose of this email:

This email introduces new users not only to Grammarly the product but also Grammarly the brand. This email has some interesting features:

  • Emotional connection to the mission of improving writing
  • Introduction to the multi-channel nature of Grammarly
  • Quick and simple how-to
  • Ability to set preferences on the types of incoming emails
  • First invitation to upgrade

What we can learn from this email:

Personally, we love the fact that Grammarly shares the “why” behind their brand before moving into the product explanations. This can serve as a great template for apps and SaaS products. Start with why you do what you do, then talk about where they can use the app, and how.

Next, Grammarly sends a second welcome email to new users.

Grammarly's strategy

The purpose of this email:

In this email, Grammarly dives deeper into something that was introduced in the first welcome email: the fact that Grammarly can be used across many devices.

What we can learn from this email:

With your first email, you want to give new users an introduction to the highlights of your brand and your product. With the second email, go into more detail on the most important thing users need to know. For you, that might be used across devices, or it might be an overview of the top features or products.

Grammarly's upgrade emails

After those two emails, Grammarly doesn’t waste any time. They go straight into offering the Premium upgrade, and these upgrade offer emails continue every week.

Grammarly's best emails

The purpose of this email:

This email does a great job of showcasing the features of the Premium plan, as well as the results of using it. The “Premium Spotlights” are actually blog post titles, but they hit an emotional nerve with people who are worried about their writing ability. So in this way, Grammarly is selling the product while sharing content. Smart!

What we can learn from this email:

Use emotional persuasion tactics in your emails without resorting to sleazy copy that pokes at people’s pain points.

Here’s another upgrade offer email, which is the fourth email that the new user receives.

Grammarly's upgrade offers

The purpose of this email:

This email clarifies what isn’t included in the free plan and gives the user a timely offer to upgrade to their annual plan.

What we can learn from this email:

Put your pricing table in your email, but without the pricing to encourage more users to click through to view the discount.

Better insight emails

The Grammarly team is definitely having a lot of fun innovating their emails. On top of their newsletter with blog content and interesting tips and tricks, they’ve added insights to show how the user ranks against all of their 20 million users around the world.

Grammarly user engagement

The purpose of this email:

This email engages with the user in a friendly, upbeat, unique, and positive way. Plus, it deepens the relationship with highly personalised email content, including:

  • Number of weeks the user has written consistently
  • Productivity in terms of words checked compared to other users
  • Mastery in terms of accuracy and errors
  • Vocabulary in terms of unique word usage
  • A personalised reason to upgrade to Premium with stats on what else could be fixed if they were a Premium user

What we can learn from this email:

Can you personalise the way that you’re engaging with users? Even better, can you personalise the way that you’re encouraging users to upgrade? Can you inspire FOMO by telling them what exactly they’re missing out on? Collaborate with your product team and see what you can achieve.

Don’t you just love those insights emails?

Here’s another example:

Grammarly's user update emails

The purpose of this email:

Again, the above email does a great job at personalisation. But it’s more than that. It’s gamification on a global scale. Users all around the world can see how they stack up against one another.

What we can learn from this email:

Use product statistics to inspire users to use even more features of your product. Offer stories and tips that relate to the product and what users care about.

Churn-reducing emails

What happens when something goes wrong? What happens when a Grammarly user isn’t using Grammarly?

Well, they get an email like this one…

Churn reducing emails

The purpose of this email:

This insights email shows users that their stats are big fat goose eggs across the board. Of course, it’s the same insights email as above, but with more an error message worked into it.

What we can learn from this email:

If you don’t have something that you send to regularly showcase individual product usage statistics, you can still take this email as inspiration for what to say to users that are inactive or haven’t touched certain product features.

Notice how they give users a reason to get their account working properly.

Premium upgrade offers from Grammarly

As mentioned above, Grammarly doesn’t quit sending those upgrade offers.

Here’s one of many examples:

Grammarly upgrade offers

The purpose of this email:

With this email, Grammarly stays in touch with active users about offers and reasons to upgrade to Premium.

What we can learn from this email:

Not following up is a mistake that many SaaS companies use. After their free trial sequence ends, they stop communicating about the upgrade. Well, Grammarly doesn’t. They just keep on going, and so should you.

How to get your email timing right

We’ve shown you a ton of emails. You’re probably wondering how Grammarly works all of these in.

You can get a bird’s eye view into how Grammarly balances value with sales below:

Timing of Grammarly emails

They send emails pretty frequently, but there’s a great balance between the “Grammarly Premium” sales emails and the “Grammarly Insights” user statistics and content newsletter emails.
This balance keeps the user opening their emails. If it was just sales email after sales email, they would probably be ignored.

Key takeaways

Now can you see why we have a crush on Grammarly’s emails? Join the fan club.

Here are some of the things to keep in mind and put into action:

  • Don’t give up on converting free trial users into paid users
  • Gamify onboarding and engagement if at all possible
  • Utilise product stats if at all possible
  • Use emotional and psychological triggers into content to help you sell paid subscriptions
  • Balance adding value with asking for sales
  • Use your company mission in your welcome email and throughout newsletter content

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Written by
Dayana is a B2B SaaS copywriter and content marketer who lives in Northern California. She loves messaging and storytelling alike.

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