Here’s What’s Wrong With Your Trial Expiration Emails and How to Fix It

Kalo Yankulov

Kalo Yankulov

Co-founder and marketer at Encharge.

As marketers, we’re full of hopes and dreams. We love to fantasize about all the little handy-dandy things that can turn around our business.

Well, let me that annoying neighbor that drills holes on the other side of your wall and shake you up from your dream today:

Your trial expiration emails are a marketing gimmick, and you are using them in the wrong way.

If there’s one thing that we’ve learned as marketers is that people have the attention span of a goldfish, and it’s our job to remind them about our amazing product/service/offer.

Therefore, when a trialist loses interest in our software, we think that sending just one more email, text message, or retargeting campaign on Facebook could close the deal. That’s when we implement the powerful trial expiration email and start sending desperate messages like this:

free trial expiration email from screenhero

Busting the trial myths that you build your expiration emails upon

Myth #1: A signed up user is an interested user

It’s a sound assumption. To reach the first screen of your app, users need to go through your homepage. Your whole marketing funnel is based on the premise that a signed up user is someone who’s “interested”, right?

Not necessarily. Just because a user has signed up to try your tool doesn’t mean they understand what your tool does, let alone be interested in becoming a customer.

As much as I want to tell you that you’re a special snowflake, there are over 1 million company pages on LinkedIn with the keyword “SaaS”. A ton of these companies offer a free trial, and a ton of people try tools left and right for the right or wrong reasons.

If we’re to break down your trialists into segments, we’d probably end up with the following (or similar) groups:

  • Opportunists — the people that tried your product because, well, it was free to try.
  • Unqualified users — the ones that you don’t want as customers, because they’re likely to churn.
  • Qualified users that have the problem, but don’t see your product as the solution.
  • Users that have the problem see you as a viable solution, but that haven’t experienced value, yet.
  • Users that have experienced value with your product within the trial window.

Yet, we treat all of our trialists like qualified users that have experienced value with our product.

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Hence in our trial expiration emails, we write stuff like “we’d love to keep you as a customer”, “you’ll fall in love with our product”, or even worse, passive-aggressive prompts like “going to assume that your business is not a priority at this time.”

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Let’s review each of these:

“We’d love to keep you as a customer” — hell no, you don’t want to keep unqualified users as customers. Those will skyrocket your overhead and churn rate.

 “You’ll fall in love with our product” — nope, they won’t if they don’t have the problem your tool is solving for.

If you’re not going to upgrade “I’m going to assume that your business is not a priority at this time.” — or maybe you haven’t provided enough value or explained why they should upgrade…

This is not a terrible copy if all of your trial users fall under the bucket of people that are interested and have experienced value with your product within the trial period. These people barely require any work to convert, so you don’t have to be a copywriting genius anyway. 

Unfortunately, that’s rarely the case.

Instead, we need to qualify our leads and consider the real customer journey when we craft our expiration emails.

This leads us to myth #2…

Myth #2: An expired trialist is an activated user

SaaS people think of the trial end date as this magical milestone when users are most likely to convert.

The reality is that the trial period is an artificial urgency, created by us. As Lincon Murphy says: a “Marketing Gimmick”. It’s a gimmick we use to push people to convert.

Nothing has changed for your users in 7, 14, or 30 days. People are going to experience value at their own pace regardless of your trial length.

Why?

Because life happens, and they have other things to do.

Simply putting a limited time window for people to try your product, doesn’t mean they have activated features, solved problems and experienced value within that timeframe.

That’s why we need onboarding emails to get people back to the app and remind them about how your software helps them achieve their desired outcome.

Myth #3: Users always upgrade within the trial window

A report by Madkudu shows that 50% of SaaS conversions happen AFTER the trial ends. In fact, MadKudu mentions that most companies had customers converting 6 months after signing up.

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Another important thing to consider when we think about people upgrading is Parkinson’s law in the context of SaaS trials:

The time to evaluate your product will expand to fill the time available to try the product for free.

In other words, even if your users are activated, they’d still wait for 7/14/30/60 or however many days your trial is to become a customer.

With freemium products, there’s no artificially created time window. That’s why freemium products see a bigger portion of their users converting quicker than free trial products.

To sum this up:

Your trial length would have some impact on how fast (or slow) people upgrade, but people would ultimately convert at their own pace whenever they experience value with your product.

Since your trial expiration emails are time-based, this means they don’t take into consideration the activation pace of the user. That’s why trial expiration emails don’t work well in isolation.

Trial expiration emails don’t take into consideration the activation pace of the user.

Instead, I want to propose a better trial expiration strategy that works with the pace of the customer journey. So let’s dive in.

A better approach to trial expiration emails

Trial expiration emails are a powerful instrument, but they don’t work well on their own.

What I propose instead is an onboarding flow based on the activation pace of your users.

To persuade users to subscribe to our product, we want to send three sets of emails (or sequences) based on when users have achieved the aha moment and experienced value in your app:

  1. Experienced value before the trial ends → Send Upgrade Email.
  2. Experienced value and trial ends soon → Send a Trial Expiration Email with a prompt to upgrade.
  3. Haven’t experienced value and trial ends soon → Send a Trial Expiration Email with an extension option.
  4. Trial ended, and the user hasn’t converted → Ask for feedback

Let’s unpack each segment and the respective emails.

Send Upgrade Email to users that experience value before the trial ends

There is a set of features or activities that every user needs to do in order to become an “active” user. These are the things that all or most of your paying customers do during their trial.

Once you what are these activities, you can use a marketing automation tool to segment people based on them and create trigger-based onboarding flows.

You can see such a flow below:

Let’s take a step back and see how this flow works:

1. Event — “Trigger on Event Signed up”. The flow starts here when a user signs up.

2. Send Email — “Welcome email”. We send the first email.

3. Wait for 3 hours.

4. Hast Tag —  “sent-request”. On this step, we’re checking if the user has completed a critical activity in the app. In this case, it’s “Sending a request”.

If NO → We sent a Nudge email getting them to take the action. Then we wait 1 more day and check if they’ve completed the next required action “Request criteria met”

If YES → We check if they’ve completed the next critical trial activity “Request criteria met”

5. Has Tag —  “request-criteria-met”

On this step, we’re checking if the user has received their first completed Request Criteria.

If NO → We sent another nudge email.

If YES → We sent “Criteria met — sales/upgrade email”.

6. We send the Upgrade Email.

—–

In this flow, the user will receive the Upgrade Email whenever they have become an active user, a.k.a have experienced value with the product, a.k.a have done all of the critical activities in our trial.

The Upgrade Email will get send even if the user trial has not expired yet. For example, if a trialist becomes an active user on the first day, they’re going to get the upgrade email.

The goal of the upgrade email is to give that last push your active users need to upgrade. It’s advised to create urgency in this email.

Below is a great upgrade email example from MindMeister.

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This email works well because:

  • It’s sent at the right time. When I created a few mind maps.
  • It’s personalized. It’s triggered when I tried to use their “custom styles and boundaries” feature.
  • It uses scarcity to nudge me to upgrade.
  • It has a single clear call to action.

Another way to approach this is to reward users for doing things in your app. Grammarly does a great job of getting people to upgrade when they start to write actively in the platform:

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Send a Trial Expiration Email to active users before their trial ends

The second case we have is when users experience value within the trial window, but their trial ends soon.

SaaS onboarding email expert Sophia Le recommends doing these three things to get people to upgrade:

1. Emphasize what the user will miss out on by not upgrading to a paid plan.

2. Contrast the outcomes of upgrading vs. not upgrading.

3. Provide a single call-to-action in your trial expiration email.

So let’s unpack these:

1) Stress what trial users will lose by not upgrading

It’s called loss aversion, and we have covered this tactic in some of our email teardowns.

There are two ways you can approach loss aversion in your trial expiration emails:

Quantify the value that the user is currently getting from the product

For example:

“You currently have 5 members in your workspace. Your account will be downgraded on 24 Jan, and the following members will lose access.”

Below is an example from Airtable, asking me to upgrade my base in order to keep access to it:

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Another example from Zapier states that I’ve used XX number of tasks. Also, notice that the email later mentions my total monthly allowances, making it clear how much I left from my trial quota.

In these examples, it is clear that the user must upgrade to keep continued access to the service.

In other instances, you need to be more creative to quantify the value.

For example, if you run a lead generation platform where a user saves 20 minutes per lead, you might use the following copy:

“Tool X found 50 leads for you in the last 30 days. Our estimates show that you saved 1,000 minutes of prospecting time. To keep on saving that time each month, upgrade your account today.”

Now, this is a bit more technical but absolutely doable in a tool like Encharge that supports liquid tags. With liquid tags, you can create dynamic email content based on if/else rules.

For example:

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List the key features that the user will miss

As Sophia Le states, the goal of trial end emails is to get the user to stop and ask, “Will I miss out if I don’t grab my credit card?”

FollowUp.cc does an excellent job of stating what features their trial users lose when they fail to upgrade.

followupcc upgrade email

Still, that email could be much more powerful if those features are attached to benefits. In the example below, Sumo emphasizes the outcomes like “building a massive email list”, visits, engaged visitors.

Sumo Loss Aversion Email

Source

2) Contrast the outcomes of upgrading VS not upgrading

There are two ways you can approach email copy:

  1. Illustrate how life would look like for your customer WITH your product — easy, convenient, peaceful, rich. Picture the perfect vision of your customer, a dream.
  2. Illustrate how life would look like for your customer WITHOUT your product — difficult, poor, tedious, poor, or whatever. Picture your customer’s worst nightmares.

As a marketer, you can use emotion to contrast life before and after your tool. There’s no right or wrong approach here.

That said, Sophia recommends going with the second option — picture how life would look for your users if they fail to upgrade.

Let’s look at this final trial expiration email from Pipedrive.

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Organizing and scaling sales is pretty important, but do you know what’s even more important? Not losing hundreds of thousands of dollars of hot leads because of carelessness.

Big, juicy deals are the lifeblood of sales-assisted businesses. Salespeople would do everything to be on top of their sales cadence and reach their sales quota  — their commissions and jobs depend on it. Now Pipedrive is not just a tool for “organizing and scaling” sales but a critical lifesaver for businesses and salespeople.

Use the trial expiration email to share a case study or tell a story. Explain how your software has saved someone’s business/job/life.

3) Provide a single call-to-action in your trial expiration email.

Every email you send should have a single goal (learn more about the simple emails formula).

Your trial expiration email has a simple job, too: get users to upgrade before their trial expires.

It’s not the time to be smart or comprehensive. Avoid trying to get people to do other things like watching a how-to video, checking out new features, completing a survey, and so on. It’s too late for these anyways.

Provide clear instructions on how people can upgrade and how your pricing works.

^ I should stress this. Some SaaS products have a terribly complex pricing structure. Make sure your trialists know what they’re paying for and how they could pay you if they want to.

Send a Trial Expiration Email to passive users before their trial ends

The easiest way to execute this is to have a trial expiration flow that puts active and passive trialists in different buckets based on which segment they’re in.

You can create the trial segments in Encharge based on what activities they’ve achieved in your app. Then use a flow with a filter step “Is in Segment”:

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While your activated trialists are on the fence and could benefit from a bit of push and urgency, your passive trialists are a whole different breed.

Offering discounts to inactive trial users would be as effective as selling hamburgers to a vegan.

Also, these users haven’t experienced any value with your product, so emphasizing what the users will lose by not upgrading will not work, either.

So what are we supposed to do with passive trialists?

To tackle inactive trial users, you need to take a step back and:

  1. Offer a trial extension. This will give passive trialists more time to reach the desired value moments and will provide you with more time to qualify them.
  2. Learn more about those users and figure if they’re a good fit to invest time in nurturing and onboarding them.
  3. If they’re a good fit, explain WHY they should take the first step.
  4. Provide the path of least resistance. Try to get them to do just one thing in your app, or do it for them manually.

The easiest way to start this conversion is the “Reply to this email” CTA:

trial extension retention email design from flow

You don’t want to automate this process, as you could easily throw away resources on unqualified users. Instead, you want to keep this manual and start a conversation with your passive trialists.

You can use this response:

Hey {{name}},

I’d be more than happy to extend your trial with 7/14 days!

Do you mind sharing what are you’re looking to get from {{Product}}? I’d love to help you get set up and take some things off your plate. I know you must be pretty busy.

Best,

{{Customer Success Person}}

Ask all expired trial users for feedback

No matter how awesome your trial expiration emails are, you’ll still have a lot of churned trial users.

That segment of people gives you a huge opportunity to learn more about the quality of your acquisition efforts, your onboarding process, your messaging, and the objections your customers have about your tool.

Typeform and Google Form surveys are a great way to collect responses, but they don’t get super high engagement from inactive users. The user needs to open a new browser page, enter their emails, and answer a bunch of questions. It’s hard to get passive users to do so much.

A much smarter way that guarantees much higher engagement is the inline email survey.

It looks like this:

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When a user clicks on a specific link, the answer is recorded in Encharge. Then, you can see the people segmented by the answer they’ve given (what link they’ve clicked).

This is by far the easiest way to collect feedback from expired trials!

Trial Expiration Email Templates

Don’t feel like sweating too much over your trial expiration emails? Just steal these fill-in-the-blanks trial expiration email templates that we put together for you.

Further Reading

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