Upgrade Emails: Automation, Copy, and Best Practices for Trial End Emails

Upgrade emails are incredibly important: they help you convert trials into subscriptions and directly affect your bottom line. They can also get pretty messy in terms of the decision-making logic.

I'll show you how you can build great upgrade emails (a.k.a. trial end emails) - starting from the very basic first approach to the sophisticated, conversion-optimized setup you'll want later on.

But why should you even care about that? Here's what Sophia Le has to say on that:

"An upgrade email shouldn't be an afterthought. Use this email to counteract any remaining objections the user may have about purchasing your SaaS product. In other words, close the damn sale."

Who this article is for

First and foremost, this article is written for you, the solo-founder bootstrapping a SaaS product.

Throughout most of this article I'll assume you do not ask for credit card details during signup. When you ask for credit card during signup the upgrade email turns into a "impending charge email" and the whole dynamic shifts. This is a whole nother topic for another day.

How to read this article

This article is split into multiple sections, each addressing different stages of your product. At first we look at what you can do when you're going at it alone and have less than 100 customers.

The next section focuses on ways to improve this initial setup, once you understand a bit more about your customers and how they use your product.

In the last section I'll show you a number of possible improvements - ranging from copywriting, to personalization, and beyond - you can employ once you have some staff that dedicates themselves to making your upgrade workflow as smooth as possible.

Caveat: Unsuck your product first

Before we get straight into how to structure upgrade emails, write the copy, and the right timing, let me remind you of one thing: Upgrade emails are no cure for missing market/product fit, deficient onboarding, or bad customer support.

Frankly, if your product sucks, upgrade emails won't magically bring you hundreds of conversions.

So make sure you've got a viable product on your hands before you start to worry about this too much.

When you asked for credit card upfront

If you asked for credit card details during signup AND the user successfully adopted, things are straight-forward. You just wait for the trial to end, send a courtesy reminder three days in advance, and start charging after the trial is up.

There's no reason to sell people on your software, if they already sold themselves.

If they are not successful, you have essentially two options: either you postpone the trial end - by offering to extend their trial - or you just start charging them anyway. Then you should start sending them multiple emails about a week before the transition.

Obviously, just charging them anyway isn't the best option. Ideally, you (or your customer success team) would want to reach out and make them successful first.

My friend Jane Portman chimed in with a thought-provoking remark:

"Ethical sidenote: a significant number of paying users in any SaaS rarely use the app anyways. It isn't a perfect case, but life isn't perfect either. As a founder, I wouldn't leave money on the table, and would probably charge them as planned (with a sidenote that they're always welcome to ask for a 100% refund of the last period). This, of course, is a subject for discussion."

Lastly, you want to send them more than one reminder email to make sure you get a happy new customer - and not just someone who pays your bills for two months and then does a chargeback.

The basic upgrade experience

Okay, let's talk about the very first upgrade experience you put in place. The one you need right out of the gate. The one that is "good enough for now".

For this, I'll assume a B2B SaaS application that does NOT collect credit cards during signup built by a bootstrapping solo-founder.

That means you are facing two big problems when it comes to upgrade emails:

  1. You do not know what constitutes a successful trial
  2. You have neither time nor money to polish things up

Lets look at both problems in turn.

Lack of data & understanding of your trial users

Ideally, when you write your upgrade emails you know enough about your users and your product so that you can predict their success in using your product from the behaviour you are tracking.

The problem is that you do not have a lot of quantitative data to go by - i.e. you have less than 100 customers so there aren't any clear pattern showing up. At best you've got some qualitative data, e.g. from hallway usability testing, demoing your product, or user interviews.

Lack of time & money

Collecting that data needs a lot of customers and a lot of time for writing the tracking code, customer interviews, etc. As a solopreneur you're notoriously short on both.

There are only 24 hours in a day (8 if you want to stay productive long-term and/or have something resembling a social life) and you don't have a few millions in VC money that you can throw at the problem.

Solving these problems with an 80/20 approach

In essence, you just don't know which usage pattern makes your trial users go from "Meh" to "Woah! This is THE shit!".

So the very first upgrade email you write contains nothing but copy and a call to action: You want your users to put in their credit card details. You start sending upgrade emails three days before the trial is up, because it is child's play with Stripe and Drip - and good enough to get started.

Let's dive in and look at the structure and the copy of your very first upgrade email experience.

Get the Upgrade Email Workflow Blueprint for Drip

Sign up for my mailing list and get the Upgrade Email Workflow that you can install instantly in Drip to increase your trial-to-paid conversion rate.

Additionally, you'll get the SaaS Email Marketing Crash Course - a 5 day course to double your MRR with the help of world-class email marketing - as well as periodic (up to about once per week) emails containing more content and/or promotions of interest to you. You can unsubscribe at any time. We'll keep personal data according to our Privacy Policy

I won't send spam. You can unsubscribe any time you like.

The structure

The structure on the upgrade notifications workflow straightforward: When you receive the customer.subscription.trial_will_end event from Stripe, you push the user into this upgrade workflow.

The workflow sends your trial users one email every 24 hours until the trial ends. Because the trial_will_end event comes three days before the trial is up, this results in 3 emails:

The workflow also checks whether a user has entered their credit card details prior to sending each email and exit the workflow if so. That way you do not bombard converted users with useless emails.

This is what the workflow looks like - designed in Drip:

Basic upgrade email workflow in Drip

The copy

Due to the lack of data - e.g. you don't know whether a given customer is successfully using your product - it is a lot harder to write great copy.

Ideally, you want to include some metric telling them how much they have used your app or how much money they've made because of it. But that is to be perfected later on.

For now, we will focus the copy on highlighting the benefits and features and include social proof to counter the most common objections. If you are conducting any sort of exit interview with your customers after they cancelled or didn't convert from the free trial, you'll quickly figure out those objections.

Here's what that first email could look like:

Basic upgrade email copy

The second email, sent 24 hours later (or 48 hours out) has more urgency and also a bit more details on what happens.

trial end email copy

The third email is pretty much the same as the second one except for the changed deadline.

trial end email copywriting

Summary of the basic upgrade workflow

This basic upgrade workflow starts three days before the trial ends and sends three emails - each 24 hours after the previous.

It does not contain any personalization aside from the user's first name. The copy is good, but could be more tailored to the reader. It's a starting point - no more, no less.

I encourage you to experiment with how many emails you send, because sending an email twice increases your conversion rate by as much as 50%. So don't shy away from sending the same email twice - maybe with a different headline.

Get the Upgrade Email Workflow Blueprint for Drip

Sign up for my mailing list and get the Upgrade Email Workflow that you can install instantly in Drip to increase your trial-to-paid conversion rate.

Additionally, you'll get the SaaS Email Marketing Crash Course - a 5 day course to double your MRR with the help of world-class email marketing - as well as periodic (up to about once per week) emails containing more content and/or promotions of interest to you. You can unsubscribe at any time. We'll keep personal data according to our Privacy Policy

I won't send spam. You can unsubscribe any time you like.

100+ customers: Stepping up your upgrade email game

Sweet! You've got a basic upgrade experience and some emails in place. You've worked hard to improve your product and it's going well. You have got a few dozen people using and paying for your app.

First of all, congratulations on the success so far! I know this was hard. Take a moment and bask in the glory of your success.

Okay, that moment is over, let's get back to work :-)

Easy ways to improve your trial end emails

I'm assuming that you are either still going at it alone or with a tiny team of freelancers. Which means you've got a bit more time and also a bit more money to spend on things, but you're still far from spending like there's no tomorrow and you're still wearing not just many, but all the hats.

So here are some ideas on how to improve your upgrade emails that aren't too burdensome:

1. Track feature usage & user behaviour

Tracking feature usage and user behaviour is the foundation for most of the following tactics. It helps you personalize your emails and figure out the Minimum Path to Awesome (MPA - more on that later), so you should start collecting this data as soon as possible.

You can do this with tools such as Mixpanel, which comes with a free plan for up to 20,000,000 tracked events per month - that should be sufficient for a while. Additionally, you'll probably need to track some of this stuff in your own code/database.

Here are some must-have metrics for your app:

  1. Last login time
  2. Last time active in the app
  3. Number of logins
  4. Usage of metered features

When you count the "number of logins" make sure you not only count the times a user put in username & password, but also how often they returned to the app after a period of inactivity - e.g. two hours. If you remember their login for 30 days, all your trial users will have a login count of 1 - no matter whether they are using your app daily or never.

"Usage of metered features" means that when you are selling 3-4 different pricing tiers of your product and you differentiate those tiers by how much some feature gets used, you should now start tracking that usage - if you don't track already.

With those metrics you'll be able to implement some of the following improvements to your upgrade emails:

2. Better timing

Another thing you can do to improve overall conversions is to ask for the upgrade at the right time.


What happens when you leave your pizza in the oven for too long and it comes out half-charred? You're less likely to eat it - right?

The same happens when you wait until the last minute to ask your users for the upgrade. Maybe they were ready to buy days ago.

Here's what expert Kate Harvey has to say about that:

The days of sending emails based solely on the number of days they’ve been trial users are over. Heavily engaged users may be up and running within a few days while other users may not have logged in since signup. Sending all users the same email at the 3 day mark will alienate users because it is obvious you aren’t in touch with their needs and use of the product. That’s where action based (also called “behaviour based”) emails come into play.

Finding the right time is all about monitoring user behavior and to use lead scoring. You give your users points for actions they take:

Once they hit a threshold, you ask them to upgrade. Then experiment with the threshold to improve your conversion rate further.

Again, UX expert Jane Portman had some great advice to share with us:

You can do it via in-app message — using a tool like Intercom — or by scattering upgrade buttons in strategic parts of your user interface. The latter might be even better because you're not specifically starting a conversation (therefore not creating an uncomfortable feeling for the user).

I would add that to the existing emails - i.e. you ask when the time is right AND at the end of trial in case they didn't upgrade by then.

That's why you need to track how often people return to your app as well.

Did they use the app 15 times in the first 5 days of the trial? There's a good chance they are already seeing the value in your app. Offer them an upgrade.

Did they log in once, close the tab after 10 minutes never to be seen again? Time to re-engage that user!

3. Mention key feature usage

Another great way of increasing your conversion rates is by further personalizing your emails.

You can personalize the email by stating things like "You have used 63 out of 100 fuzzies". Here's an example from Zapier:


4. Suggest the appropriate pricing tier

Zapier also used another great trick in the above email: They suggest the appropriate plan for how much you're using their app. Zapier centers this around usage of their key feature ("automated tasks"), but you can also take into account usage of premium features in your app.

Suggesting the right tier makes signing up for a paid plan easier, reduces friction, and increases your conversion rates.

5. Segment your list

Your conversion rates increase the better you are able to help each and every user. The problem is that every user needs help with different topics.

Take the readers of this article as an example: Some of you haven't even started building a SaaS product and want to learn about the minimum effort necessary. Some have launched their product, are pushing moderate revenue with a small team, and want to grow. And some of you might have a 5M+ ARR, a team of 20, and want to learn what else your devs/marketers can improve.

You solve this problem by segmenting your users. The easiest way to segment them is through self-selection. In your sequence include an email where you ask people what describes them best. Allow them to self-select by clicking on different links in that email.
Depending on which link they click, you tag them in your email marketing software, and proceed to send them the right content.

For example, when you are selling a procurement tool to medium sized businesses you can create a segment of users without buying authority within their organization. You subsequently provide them with reports, explanations, or other material designed to persuade the stakeholders to buy your software.

Alternatively, you send C-level employees case-studies of similar company who streamlined their processes with your SCRUM software and doubled the number of shipped features per month.

These are just some examples of segments you can target. You can segment your users by their level of experience, company size, job title, etc. You can even segment them by multiple verticals at once - "web developer working as a freelancer"? "Designer running his own agency"?

Remember to always provide a default segment - i.e. a variety of content that is sent to people who do not click on any links. For those people it is a wise idea to send the segment selection email again and if they don't click on anything in there, ask them why they didn't. Maybe you'll learn about a new audience you're attracting.

6. Write better copy for your audience

The emails I gave you to start with aren't tailored to any audience - especially not yours. The copy is bland. Boring. It's like grits - except you're eating the packaging.

Write some better copy - or get someone to do it for you. I don't care. Just do something about it.

Use some humor in there. Here's what I did in one of my emails:

Use humor in email copy

Don't be afraid of that. You've got nothing to lose from sounding remotely like a human being.

Or use some emojis - did I tell you that I love emojis? 😊

In fact, I love them so much, that I dedicated a whole article to using emojis in marketing emails 📧

7. Promote "sticky" features

Every SaaS app a set of "sticky" features - features that make your users stick around and convert into paying customers.

Take this email here: Geckoboard minimum path to awesome lifecycle email Image from GetVero

I bet that Geckoboard didn't just randomly decide one day to push this feature. They chose this feature, because it's a sticky feature.

Take a wild guess (or use some of the data collected in step 1) and promote your app's sticky features.

Section Summary

Implementing the above improvements helps your thriving product grow at an expedited rate. Some of the improvements, especially the gathering of additional metrics, will only take full effect at a later stage. Nevertheless it is crucial to start collecting that data now, else you'll find yourself at a crossroads without a clear idea of which path to take.

Beyond 1,000 customers: Fine-tuning your upgrade workflow

Once you have around 1,000 customers you're approaching $1,000,000 annual run rate pretty fast. Again, congratulations on your achievement. That wasn't easy and you damn well deserve a little party.

Now is also the time for you (or rather: your team) to fine-tune all the things about your upgrade emails. In this section you'll find more ideas for you to try out.

Even better™ upgrade emails

Now - at the latest - comes the time where you will no longer be able to talk about "your upgrade email", because there will be so many different ones - for different paths your users take in their journey through your app.

There will be the plain, vanilla upgrade email from earlier on a few days before the trial runs out - granted with much improved copy. But there will be one right after the user takes action X related to your app. There will be one for people who didn't use the app at all. There will be one for... you get the idea.

Your humble upgrade email has matured into the T-1000 of upgrade email marketing automation workflows.

How do you get there?

Finding the Minimum Path to Awesome (MPA)

The most impactful adventure in trial lifecycle emails (the extension of your humble upgrade email) is to discover the Minimum Path to Awesome (MPA) for your application.

The MPA is the magic sequence of actions a user has to take to be successful in your app. It is different for each app and discovering it gives you a blueprint for the emails (and in-app messages) you need to write to each user at each step along the path to maximize your trial-to-paid conversion rate.

This article on the email that decreased Moz's churn rate by 40% is an excellent (if accidental) example of the power of the Minimum Path to Awesome.

Once you have discovered the MPA for your product, the upgrade email is merely the last step along the path and by the time you send it, the user is already sold on your app.

Finding the MPA for your product is a journey that takes weeks or even months of studying data, customer interviews, and hallway testing. During your research you need to find what active users have in common. Some questions you might be asking during this phase are:

Understanding how customer success manifests itself and how it is achieved, allows you to perfect your onboarding. A perfect onboarding experience in turn improves the conversion rate on your upgrade emails.

Prevent user churn with "red flag" metrics

The opposite of the Minimum Path to Awesome is called "red flag" metrics. Red flag metrics indicate that an account is not successfully using your software and likely to churn.

Common red flag metrics are number of logins per period (e.g. logins per day) and first session duration.

There is an amazing article/case study on the KissMetrics blog that I encourage you to read up on!

When you have a user with positive "red flag" metrics, make sure to re-engage them ASAP. An easy way - besides promoting their next step in the MPA - is to offer them a trial extension.

Automating list segmentation

Another seriously advanced technique is to automagically segment your list by keeping track of the following:

These informations can give you a pretty decent idea of which marketing persona each user fits - without your users needing to self-select. There are so many hints you can take from the smallest of user interactions and combine them into incredibly effective marketing automation workflows.

The master of this technique is Brennan Dunn, who just launched a SaaS app around the concept. If you'd love to show every website visitor a custom version of your website, check out RightMessage.io.

Section Summary

Making the most out of your upgrade emails pretty much comes down to finding the Minimum Path to Awesome and guiding your users along that path. Once you have time & money to make this optimization, do it!

Random tips for your upgrade emails

Here are a few more tips that defied being put into any of the categories above.

Use Loss Aversion to your benefit

People are inherently afraid of losing something they already have. That is a trait you can exploit.

First of all, you need to create a sense of ownership. Your user needs to see the value in your product (again, unsuck your product first!) and feel "this belongs to me".

One way is to start users on a trial with premium features. That way they have something they will lose once the trial ends.

In your upgrade emails use language that signals the impending loss - e.g. a call to action like "Get the features back".

There are a lot more tips in this excellent article on customer.io.

Even more tips for your upgrade emails

Here are a few more quick-fire tips to optimize your upgrade emails:

For even more tips and tricks, check out this article on increasing trial conversions written by Kate Harvey.


Before I wrap this up, I want to thank a few people without whom this article wouldn't be as comprehensive as it is now.

have helped me tremendously with feedback on my drafts, quotes, and new insights. Thanks a lot for the help!


Upgrade emails are important for your business success, but as with so many things you got to start somewhere and then iterate from there.

The basic workflow outlined above, gives you a good starting point. And there's a ton of ideas to improve on it, too.

Get the Upgrade Email Workflow Blueprint for Drip

Sign up for my mailing list and get the Upgrade Email Workflow that you can install instantly in Drip to increase your trial-to-paid conversion rate.

Additionally, you'll get the SaaS Email Marketing Crash Course - a 5 day course to double your MRR with the help of world-class email marketing - as well as periodic (up to about once per week) emails containing more content and/or promotions of interest to you. You can unsubscribe at any time. We'll keep personal data according to our Privacy Policy

I won't send spam. You can unsubscribe any time you like.