Upsell a Free User into a Paying Customer with Email Automation

Upsell a Free User into a Paying Customer with Email Automation


Launching a new digital product is exciting!

On Day 1 you just wanted people to sign up to use the product you took so long to build; there is a ton of satisfaction in that. However, satisfaction doesn’t pay the bills, so at some point, you need to upsell your users into paying customers.

If you have a really expensive SaaS product you might use a dedicated sales team to help convert free trial recipients or free users into paying customers. However, if you have a lost-cost subscription product there likely won’t be enough margin to pay for a sales team to help upsell your product.

That’s where really great email automation comes into play for you. It’s less intrusive for your users than a sales call, and it should be low-cost enough for you to execute without cutting into your margins.

Let’s take a look at how Grammarly uses email to upsell its users into paying subscribers.

What is Grammarly?

Grammarly is a free browser extension that helps its users “compose bold, clear, mistake-free writing with Grammarly’s AI-powered writing assistant.”

Basically, it provides corrections for spelling and grammar mistakes when users are typing in popular digital platforms such as Gmail, Outlook, Facebook Messenger, Slack, Salesforce, Google Docs, Twitter, LinkedIn, and many other sites.

Screenshot of Grammarly email automation

Grammarly has a 5-star rating from over 34,000 users, along with a total user base of over 15 million people.

The Upsell Opportunity 

The basic version of Grammarly’s browser extension is free. However, they also offer two paid versions.

There is a Premium version that offers advanced checks for punctuation, context, and sentence structure. The premium version costs between $11 and 29 per month. There is also a Business version that allows companies to offer Grammarly to employees for $15 per month.

Screenshot example of a Grammarly premium correction

If Grammarly can convert even 5% of their 15 million users into paying customers that’s 750,000 customers. At even the lowest pricing tier of $11 per month x 750,000, that’s a recurring revenue base of $8,250,000 per month.

So converting as many free users into paying customers presents a huge upsell opportunity for Grammarly.

Now, getting a user who signs up for a free browser extension to upgrade to the premium version would be very hard without email marketing. Once users install the free version of the extension, how would Grammarly ever present them with the opportunity to upgrade if they couldn’t send users a message to their inbox?

Luckily they can because signing up requires submitting your email address.

Using Email Automation to Upsell Over Time

When a new user first signs up for Grammarly, he or she will receive a welcome email that has the email subject line, “Get the Most Out of Your Free Account.”

Screenshot of Grammarly's welcome email to new free members

This is a great subject line because it subtly lets the user know that there is a paid version since it specifically mentions that the user is on the “free account” version. It also indicates that there is a ceiling to the free account since it says “get the most” out of it.

One week later, Grammarly sends out the first email in its upsell automation campaign. The subject line says “Upgrade to Grammarly Premium, Become a Stronger Writer.”

example of upsell email number one from grammarly

This is a great subject line because it is clear, concise, and includes a benefit that is important to the user. After all, the person wouldn’t be using the free version of Grammarly if writing improvement wasn’t a goal.

This email sends the user to the upgrade page that clearly explains the benefits of doing so.

Screenshot of Grammarly upgrade page

If the user doesn’t upgrade right away, Grammarly automatically sends another upsell email two days later offering a 40% off discount! The subject line is “Write Like a Pro: Here’s 40% off Grammarly Premium.”

Screenshot of Grammarly upsell email offering 40% discount

Again, this is an excellent subject line because it includes a benefit and then an exciting offer – 40% off! That’s a big discount! The email message itself creates urgency because it has a fast expiration date. You must upgrade within the “next 2 days” to get this amazing offer.

Finally, when the offer is coming close to expiration two days later, Grammarly sends out a “Last Chance” email.

Screenshot of Grammarly upgrade email

Now at this point, it’s only been about 10 days since the user first signed up for a free account. He or she may not yet be comfortable enough with Grammarly to upgrade to a paid account.

This is where the “new free user” email automation campaign ends. After this, free users start receiving a monthly email that encourages them to upgrade. This monthly cadence is nice because it’s not too invasive, but provides a frequent reminder that an upgraded option exists.

The monthly emails tend to be themed for the time of year that they are sent, and almost always include a special discount.

For example, I signed up for a free account in October and in November here is the monthly email they sent offering 50% off for “cyber savings.”

screenshot of november monthly upsell email

Cyber Savings makes sense because November is known for Black Friday and Cyber Monday sales.

Then the monthly email in December was themed around planning for the new year:

screenshot of monthly upsell email themed for new year

This time instead of offering a monthly discount they try offering a discounted annual option. Playing around with different offers is a great way to try and convert users who haven’t taken action on previously used sales. Sometimes you just have to frame an offer the right way to spark a conversion!

In February the monthly email went back to 50% off, which is a truly great offer and one worth revisiting.

screenshot of grammarly monthly upsell email

I’ve been a free user now for about four months, and every time I get one of these emails I am tempted to upgrade to premium. I’m sure that I will at some point.

The Business Case for an On-Going Upsell Email Series 

You may be thinking that putting together an on-going upsell email series requires time, and time equals money. You wouldn’t be wrong, but let’s just remember the upside: converting just 5% of free users into paying customers at $11 per month equals $8,250,000 per month in recurring revenue for Grammarly.

Now, we know Grammarly is offering most users a discount of up to 50%, but even so, that equals a recurring monthly revenue of $4,125,000.

Revenue doesn’t equal profit, but $4 million per month in recurring revenue seems to have a lot of margin for a browser extension business. In full disclosure, I say that without any intimate knowledge of their financials.

What is the upside for your business?

A Case Study Worth Copying 

If you’re currently running a low-cost software company on a freemium model, Grammarly’s approach to upsell email marketing is worth copying.

Of course, you don’t need to copy their 40-50% off discount offers if your margins are thinner than theirs seem to be, but the cadence of their emails is strong for an upsell series.

If you don’t yet have an upsell email series working for you, get started today with putting one together. It’s a time investment that can pay you back with major ROI since it’s largely “set it and forget it.” The first few emails in the series will be evergreen, and then after that you just need to write one email per month.

Of course, if you see that the frequency of the emails isn’t working for your audience you can and should make adjustments. This case study offers a great jumping off point.


Share this post

Share on facebook
Share on google
Share on twitter
Share on linkedin
Share on pinterest
Share on print
Share on email