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SaaS Onboarding Email Blog

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Grammarly Onboarding Email Breakdown

Grammarly helps me be a better writer, but can I help them be a better email-er? (Yikes, back to Grammarly I go)


Series Overview

Grammarly is spellcheck on steroids. It’s a service I actually pay for, but for this onboarding breakdown I signed up with a new email for a free plan.

Over the first 14 days, Grammarly sent me seven emails. Between days 14 and 30, Grammarly sent me three emails. Days 30 to 60 brought three more emails. Since I was on the free plan there’s no defined “free-trial” period.


Below is a screenshot of what the emails looked like in my inbox over the first 60 days.


Day 1.1: Welcome


Subject Line: You + Grammarly = Ready for Action

Sender Name: Grammarly

Send Time: Immediately after signup

Objective/Content: Introduce Grammarly and different uses

CTA: Too many to list…


Grammarly starts the email by sharing their outlook on the power of writing. This is the kind of stance and mission statements that I love to see in the welcome email. It lets me know that they’re all about, and I can see if our values align.

What to learn from it:

  • Go ahead and wear your heart on your sleeve — let your people know why you care about what you do


Holy overload, Batman. I appreciate that Grammarly has many ways they can help me, but there’s a lot going on in this email. There are so many options of what to do next that it might be analysis-paralysis inducing.

There are some sections of this email that could be their own, standalone email. Take the animation below, for example. The “how to use Grammarly” section would be a great email for the beginning of the sequence.


What to learn from it:

  • I know you’re excited but take a deep breath. No matter how wonderful cold lemonade is on a hot summer day, you can still drown in lemonade. Limit CTA options and feature spotlights so as not to overwhelm people.

  • If you currently have mammoth emails, consider splitting them up. Determine which sections are the highest priority and give them their own spotlight

Day 1.2: Introduce the Building Block


Subject Line: You’re Missing the Best Part of Grammarly

Sender Name: Grammarly

Send Time: Day 1, 12:10 PM CST

Objective/Content: Prompt me to download the Chrome Extension



For a moment I thought this was an odd email to send on the first day. After all, I didn’t think a web browser extension was the “building block” of the product. Wouldn’t they want me to open Grammarly and put a document in to get checked?

And then it dawned on me — this is genius. First, installing an extension takes about two clicks and five seconds. It’s an easy task. The real beauty of this action is what happens afterward, though. You see, once a person installs the extension, they don’t need to paste a document in the editor to start reaping the benefits of Grammarly. No, no, no. They only need to continue about their day, writing emails and posting on Facebook. Without any extra work or steps on the user’s end, Grammarly starts providing value by popping in and giving edit suggestions.

The beauty of this email is that they’ve found a way to add value to a user’s day without the person even needing to navigate to their website. The value is automatic, and you can’t get any easier or faster than automatic.

What to learn from it:

  • It sounds like a far-off fantasy, but brainstorm if there are ways that new users can get value from your product without having to change their routine at all


I can see how the subject like “you’re missing out” would inspire clicks, but does it make sense that they say that on the first day? Have I even had time to miss out if I just got here? The subject line on day two’s email would probably make more sense here.

Day 2: Introduce the Building Block


Subject Line: Get the Most Out of Your Free Account

Sender Name: Grammarly

Send Time: Day 2, 11:05 AM CST

Objective/Content: Prompt me to download one of the Grammarly extensions

CTA: Instal…


Grammarly plugins are so nice they wanted to promote them twice! Normally I would only label one email in the series as an “introduction to the building block,” but Grammarly really wants me to use an extension. This time they give me more options, though, from mobile to MS Office and more.

As I mentioned for the previous email, I think it’s genius to encourage new users to download an extension. This email opens up more ways to get help automatically without adding the extra step of going to Grammarly’s site.

What to learn from it:

  • If a feature is really, really important you don’t have to talk about it once and be done. It’s possible that not every customer will open every email, so it might be helpful to repeat yourself.

Day 8: Upsell


Subject Line: Upgrade to Grammarly Premium, Become a Stronger Writer

Sender Name: Grammarly Premium

Send Time: Day 8, 11:37 AM CST

Objective/Content: Upgrade to Grammarly Premium

CTA: Try Grammarly Premium


My favorite thing about this email are the stats at the bottom — that’s their version of social proof. They’ve also covered a lot of writer scenarios with the stats, from students and people who find writing akin to pulling teeth to those that enjoy it and want to be better. I like the subject line, too. It combines motivation with a straightforward description of what they want.

What to learn from it:

  • If you can cast a wide net in an organized way, go for it. With three icons + stats Grammarly has put out different hooks that will interest different customer segments


Uh…what? I feel like the emails went from “hello and welcome” to “pay us more” without anything in between. Perhaps their assumption is that in the six days since their last email I’ve downloaded an extension and have been enjoying Grammarly’s help. They may also assume I’ve felt frustrated by limited features in the free plan and want more help. While that would be great, is that too big of an assumption to make?

What to learn from it:

  • It can be hard to know what a user is doing when your emails are time-based instead of action-based. However, I’m not sure that two CTA emails for downloading an extension are enough potential engagement to warrant an upsell

Day 10: Upsell Offer


Subject Line: Write Like a Pro. Here’s 40% Off Grammarly Premium!

Sender Name: Grammarly Premium

Send Time: Day 10, 11:40 AM CST

Objective/Content: Save 40% on an upgrade to Grammarly Premium

CTA: Get 40% off Grammarly Premium


I like that they’ve listed out the features included in Premium, but I have a suggestion in the “weaknesses” section below. They’ve also got a great, big yellow CTA button.

What to learn from it:

  • Make your CTA stand out!


Once again, I feel like Grammarly is making some assumptions about my engagement level. Who knows, maybe they’re right most of the time? It’s just that saying I've been engaging when I haven't feels more impersonal than if they hadn’t mentioned it at all.

To go back to the features outlined in the email, I think it would be interesting to place them in the previous email and switch the social proof to this email. That way, the Day 8 email is more of an introduction to the Premium plan and Day 10 is a motivational kick to drive the point home.

What to learn from it:

  • You don't have to completely change your emails to update it — try switching the order or swapping existing content

  • It’s possible for personalization attempts to backfire

Day 11: Value-Add Content + Offer


Subject Line: Your Weekly Writing Stats + Save Big on a Year of Premium

Sender Name: Grammarly Insights

Send Time: Day 11, 2:13 PM CST

Objective/Content: Summarize activity and save 46% on an upgrade to Grammarly Premium

CTA: Make sure you’re logged in, Claim 46% off


This is how personalization is done! Grammarly uses activity data to send weekly writing stats. It’s great for encouraging users to keep using Grammarly since there are achievements to unlock. I also like that there are prompts to make sure you’re logged in. They’ve also upped the ante and are offering 46% off an annual subscription instead of 40%.

What to learn from it:

  • Give users little high-fives along the way to support their work

Day 13: Use Case


Subject Line: 2019: Goals, Inspiration, and Getting the Most from Our Product

Sender Name: Grammarly

Send Time: Day 13, 8:48 PM CST

Objective/Content: Show off different goals you can accomplish with Grammarly

CTA: Get cracking


For reference, I received this email on January 2nd, which means the “2019 goal” theme was very fitting. Unfortunately, I can’t tell if they updated the onboarding series for this time of year specifically, or if this was more of a general marketing email that I got looped into.

If this onboarding email was updated to be time-relevant, very cool. However, the 2018 recap at the bottom makes me think this email went to everyone.

I also really like the Grammarly user spotlight.

They also presented the same upgrade deal in a slightly different format. Whereas before they tried to tempt me with 46% off, this time they used dollar amounts. The deal works out the same, but I’d be curious to see if there’s a significant difference between the impact of % or $ off.

What to learn from it:

  • Showing off real users gives new users a peer they can relate to

  • If your resources allow it, updating onboarding emails for seasonal events can be fun and make them feel less stock

Days 17, 21: Data-Driven Content


Subject Line: Your Writing Stats from Last Week: No Activity Detected

Sender Name: Grammarly Insights

Send Time: Day 17 + 21, 3:52 + 3:08 PM CST

Objective/Content: Highlight account activity and progress from the last week

CTA: Visit my editor, upgrade to premium


If you ever wondered what it looked like to let these onboarding sequences run without touching the product at all, this is it. I actually use Grammarly (with a different email and account) and really enjoy the weekly updates. I’ve inserted one next to the empty one so you can see what it looks like populated.

I think if it makes sense for your product and it’s fairly simple to automate, that weekly or monthly updates are amazing. They celebrate progress and encourage users to keep going. So while these emails are specific to onboarding, they do still rock

What to learn from it:

  • Be your users’ number one cheerleader — celebrate their progress

  • There are different ways to use data to customize the user experience. It doesn’t have to be behind the scenes, Grammarly lays it out in a very straightforward way and it’s still cool

Day 28, 38, 52, 59: Upsell Offer


Subject Lines:

  • Get 40% Off Any Individual Plan + Land Your Next Gig With Style

  • LAST CHANCE: Get 40% Off Any Individual Plan

  • 50% OFF Annual Plans. Love your writing this year. 💗 (sent around Valentine’s Day)

  • LAST CHANCE: 50% OFF Annual Plans


Side note, I grouped all of these together because their content is so similar.

My main takeaway from these emails is persistence. They’re hell-bent on getting me to upgrade with a discount.

What to learn from it:

  • Be persistent. You may feel like you’re being a pain, but every person may not see every email.


Um, where was this content in the early days of the sequence? Yes, the subject lines are all very much discount-driven. BUT, inside the emails are use cases, features, and tips. This is good stuff that I think would be more useful at the beginning.

The discount-only headlines also don’t let you know what’s inside. I didn’t guess there were tips, only straight up upsells.

What to learn from it:

  • Look at all the emails you already send and make sure you aren’t pushing good content to the side

  • Ironically, always leading with the discount might not be the most enticing way

Series Review

I think Grammarly has a lot of great content in these emails, but they need to be refined and rearranged. Some content needs to be swapped or moved closer to the beginning, while other emails just need to have less going on.

What was your favorite email or take away from the Grammarly onboarding series review? Let me know down below!

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