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How the Best SaaS Companies Write Upgrade Emails that Convert

Upgrade emails are your bread and butter messages. They help convince and remind people to convert and upgrade from free to paid accounts and to higher plan tiers.

Before we dive into one of the most important types of emails for your business, a reminder:
if you really want to grow conversions and upgrades, you have to lay the groundwork first. Invest in your product, onboarding, and support to bring value to people — all before you make your big asks. As Wistia says in one of its trial expiring/upgrade emails, you have to do some work up front:

“If we’ve done our jobs right, you’ve gotten a good feel for what Wistia can do for your video marketing.”

When is the best time to ask people to upgrade? There are two answers: towards the end of a series in which you build trust and value before you sell — or based on behavior such as active use, indicating that that trust and value is already in place.

In this post, you’ll find some tactics, examples, and templates for you to use to plan and create your own upgrade emails.

Quick Tips to Level Up Your Upgrade Emails

  • Make it relevant. Personalize your emails with names and pertinent details, such as how much time is left in a trial or based on certain user activity, to make your message feel relevant and timely.
  • Specify features that people will gain or miss out on when upgrading.
    Here’s an example from CloudApp that talks about gains like faster, larger uploads.
    CloudApp upgrade email benefits

On the other hand, takes the loss aversion approach, bringing up previously available features that you’ll lose when you don’t upgrade. upgrade email loss aversion

  • Include plan pricing details. Clarity around pricing is helpful for people making a purchase decision. Front makes this evident by including an image of their pricing plans:
    Frontapp upgrade email with pricing plan image
  • Use social proof to persuade.
    iDoneThis upgrade email
  • Make it easy to keep in touch.: People might not be ready to upgrade or want to cancel, but that doesn’t mean you should say goodbye to them forever. Make it easy for them to stay connected. Here’s how Wistia does it at trial expiration.
    Wistia p.s. cta to stay connected
  • Make your call to action stand out. Most CTAs in upgrade emails are basic, such as “Upgrade Now!”. Try a/b testing copy that is more specific to the rest of your email or benefits-focused, such as’s “Get them back.”

5 Upgrade Email Templates

Now let’s look at some examples and copy templates that you can start using today:

1. Free trial over: upgrade/subscribe to continue

Example: Basecamp
Subject: Your Basecamp trial has ended. Subscribe today to pick up where you left off.

Basecamp upgrade email

Take note of the subject line here. It includes all the vital facts you need to convey: the stage of the trial, what to do next, and what happens to your work.

This upgrade email also does a great job of allaying any worries and being clear about what’s to come. It explains what happens to your data, team member access, and how to pay —
while providing some social proof to get your brain to say yes.

All it takes to subscribe or cancel is a click of a button. If you’ve been getting value out of the tool — and want to “keep using” it and keep getting that valued, this nudge to give Basecamp your money should be pretty effective.

Trial Over: Upgrade Email Template

Hi Bob!

[be nice, say thanks]
Thanks so much for giving Readerific a whirl!

[main message: trial status + what to do next]
Your free month to try out Readerific has reached the end, but you can keep using Readerific to stash, organize, and share your work reads when you subscribe!

[CTA] (Keep on reading!)

[Proactively address concerns, what happens next, what happens to data]
Your library will stick around until you’re ready to subscribe and any team members you invited will still have access.

[Pricing plan or payment details]

Our subscription plans start at $8 a month. [Persuasive tactics – social proof, benefits, etc.] Don’t miss out on what everyone else in your team is reading and offline access to your library.

[open communication channel for questions and feedback]
Have any questions or feedback? Just reply to this email to get in touch!

Keep reading!
The Readerific Team

Grab your editable template here.

2. Free trial expiring – transitioning to free plan

Wistia’s trial gives people a taste of the premium life. Once that trial is over, you can either upgrade or stay on a free plan.

Example: Wistia
Subject: 3 days left in your Wistia Premium Features Test Drive

Wistia upgrade email

In this upgrade email, Wistia reminds you of the cool premium features that you’re getting to test drive (and will lose if you don’t upgrade). They also link straight to the premium features’ related documentation in case you hadn’t had a chance to try them out.

Not upgrading at this point also isn’t goodbye. The email explains clearly that you can keep using the free plan and for how long.

Trial Expiring/Free plan Transition Upgrade Email Template

Hi Linda!

[main message: trial status + what happens next]
Your Readerific trial is coming to an end in 3 days, and you’ll be on our free plan if you choose not to upgrade.

[premium benefits reminder, other persuasion tactics to upgrade, etc.]
Hopefully you’ve had a chance to check out our snazzy premium features, like the weekly reading digest, offline mode, advanced search, and work chat. Take 60 seconds to upgrade if you’re enjoying the premium reading life.

[CTA] (I’m ready for the Super Plan!)

[What happens with no upgrade?]
Not ready to upgrade? No sweat! You’ll be on the Readerific Free Plan so that you can keep checking out your library and shared reads. You’ll also be limited to 10 articles a month and restricted chat capabilities.

[Pricing plan or payment details]
Our subscription plans start at $8 a month. [Persuasive tactics – social proof, benefits, etc.] You’ll be joining a community of 10,000 smarties at great companies like Super Acme and Woogle, who are always in-the-know at work.

[open communication channel for questions and feedback]
Have any questions or feedback? Just hit reply and we’ll gladly help.

Thanks for trying Readerific!
The Readerific Team

Grab your editable template here.

3. Trial Over – extension / upgrade

Businesses will often offer extensions on trials when asked — and they will include that in their upgrade emails with a quick sentence such as “Need more time to try our app” or “Didn’t get enough time to check out our premium features?” and directions to get in touch.

Squarespace sends a whole email dedicated to the trial extension. Their empathetic acknowledgment that everyone gets busy and could use a little extra time also conveys that they understand human beings — something that often gets left out of promotional asks.

Example: Squarespace
Subject: Need more time?

Squarespace extension upgrade email

The fact that all one extra free week takes is a simple click feels like a nice gift. But note where the focus is for the call to action here — on the upgrade button.

Trial over – Extension/Upgrade Email Template

Hi Tina!

[trial status]
Your Readerific free trial has expired! [what happens to my stuff?] Don’t worry: your library and chats have been saved.

[trial extension rationale + offer]
We know how busy life gets — and thought you might need some extra time to check out Readerific. Just reply to this email or click to get an extra 10 days: (Extend my trial)

[the quick upgrade pitch]
If you enjoyed Readerific, take one minute to upgrade. Our subscription plans start at $8 a month and all include 24/7 support, the weekly reading digest, offline mode, and more!

[CTA] (Upgrade now to keep using Readerific)

[open communication channel for questions and feedback]
Have any questions or feedback? Just hit reply and we’ll gladly help.

Thanks for trying Readerific!
The Readerific Team

Grab your editable template here.

4. Hit a limit or paywall — upgrade

Send this type of email to encourage upgrades to paid or higher plans at the most opportune time, as people actively approach any limitations on usage.

Example: Dropbox
Subject: Your Dropbox needs more space!

Dropbox upgrade email

Similar to the trial-related upgrade emails, be clear about the status of the account. You can personalize the email to feel more relevant or urgent by including actual usage details.

Don’t spend too much time in this email on making a persuasive pitch. In this situation, customers are active enough to reach the next tier, so they already realize the value of your product or service. What would be most useful to them at this point is to explain any new benefits of upgrading.

Hit Limit or Paywall – Upgrade Email Template

Hi Gene!

[account status]
You’ve already saved 30 reads! Your Readerific plan is running out of library space. [what happens if I don’t upgrade?] Enjoy unlimited storage and other great Pro features by upgrading now.

[CTA] Upgrade now for more reads

[upgrade benefits]
Upgrading to Readerific Pro will get you limitless saves and shares and access to advance search and work chat features.

[open communication channel for questions and feedback]
Need a hand with anything? Just hit reply and we’ll gladly help.

Happy reading!
The Readerific Team

Grab your editable template here.

5. Announcement/pro feature = Upgrade opportunity

Here’s an email from CloudApp, educating users about its relatively new annotations feature.

Example: CloudApp
Subject: New: Annotate your screen grabs

CloudApp feature upgrade email

Great features offer opportunities to ask for an upgrade — either as part of your free-to-paid email series or a one-time announcement of a new feature or pricing plan change. With these types of emails, focus on showing and explaining your feature or change.

Announcement/Pro Feature Upgrade Template

Hi Louise!

[Describe feature/plan change and benefits]
One of our most requested features for Readerific has been full-text search, and today we’re excited to announce our new superfast, powerful advanced search feature that’s unlocked when you upgrade to Readerific Pro.

[CTA] (Start getting your search on!)

[Quick explanation of pricing & benefits of upgrading]
By upgrading to Pro for just $X, you’ll gain access to our new power search functionality, which includes the ability to use filters and operators. You’ll also get to unlimited library storage and our work chat Slack integration.

[CTA] (Upgrade to gain pro powers)

[open communication channel for questions and feedback]
Have questions or need help with anything? Just reply to this email!

Happy reading!
The Readerific Team

Grab your editable template here.