I have a confession. I love free trials.

I sign up for free trials of software like I’m getting paid for it. If a tool seems like it’ll enhance my life by even 1%, I’m willing to sign up for a trial.

Not only has my addiction led me to some of my favorite tools, but it also allowed me to fill my inbox with tons of free trial emails.

I’ve been through the trial email flows of dozens of SaaS products and have seen some of the best and worst emails of my life.

So I decided to put on my conversion copywriting hat and spent hours analyzing these emails to pinpoint their strengths and weaknesses. I looked at what they had in common, the tactics they were using and what separated the good from the bad.

I combined that with my own email marketing experience, and condensed it into this article.

I’m going to break down how to write effective free trial emails that’ll help you convert trial-users to paid customers, using real-life examples and custom templates you can take.

8 Types of free trial emails + templates

The goal of free trial emails is to convert free trial users into paid customers. It’s difficult to do that in a single email.

So instead of just giving you a bunch of random templates, we’re going to create a free trial email series, consisting of eight types of emails.

Depending on the length of your trial and your marketing strategy, you might not use all eight. But this will give you a starting point to create your free trial email flow.

Here’s an overview of all eight free trial emails, plus examples and templates for each type.

Tips for sending welcome emails:

• Give them an overview of what to expect during their trial
• Let the user know how to get in touch with you (make it easy)
• Push them back to your product

Tips for sending educational emails:

• Keep each email focused on one new thing to learn (one tip, one webinar, or one guide). Otherwise you risk overwhelming free trial users with too much info at once.
• Focus on tips that’ll help them get their “aha” moment sooner. What’s the main use-case for your product, and how can you best educate the user to see the value of it?
• Show, don’t just tell. The reason webinars, guides and images/gifs work well is they allow users to really see what they can do with your product.

Template

3. Check-in email

How would you feel if you met someone new and were getting to know them. But every time they reached out to you, they asked for something.

Whether it’s a ride, borrowing money or anything else that benefits them more than you, every time they contact you it’s about them. They don’t even ask how you’re doing.

Well, if the only emails you send to free trial users are to ask them to upgrade their account or fill out surveys, you’re like that new friend.

Don’t be that person.

At certain points throughout the trial period, send a regular “check-in” email just to see how your soon-to-be-customer is doing. No selling or pushing them to download anything.

Another reason these emails work is because you’re being proactive. Instead of waiting and hoping for users in-trial to reach out to you with issues or questions, you’re striking first. That way you can solve issues before they come up.

Here’s an example from Focus@Will.

Tips for sending check-in emails:

• Don’t try to convert them. The purpose of this email is solely to answer any questions they have.
• Make it easy for them to ask their questions. Ideally, they should be able to reply directly to your email and get a response.
• Point them to support resources. The only links in your email should be to your resource center or to log-in to your product.

Template

4. The pitch email

Now that you’ve sent them a few emails, you should feel comfortable going in for the ask. This is the email where you directly ask them to convert from a free trial to a paid subscription.

There are a lot of different ways you can approach this, and I’ll show you different options in the templates below. But your pitch needs to be strong.

At this point, the user has had the opportunity to use your product and see the value in it. So they should be warmed up. You just need to give them a reason to convert.

Here’s an example of a “pitch” email from SocialCaptain.

Tips for sending pitch emails:

• Show them the value they’ll get from converting to a paid account. Statistics and social proof work very well here (look at the SocialCaptain example).
• Use loss aversion to users even more compelled to sign up for a paid plan.
• Send this email BEFORE their trial expires. You’ll have another opportunity to pitch them again later.

Template

5. Free trial expiration email

These are the emails you’re going to send to warn users their trial is about to expire, and on the day of expiration. The timing of these emails will depend on how long your trial period is.

For instance, if you have a 30-day trial, you might want to send an email a week before the end of their trial and another one a couple of days before the trial expires. But if you have a 7-day trial, you should send it 1-2 days before the trial expires.

Loss aversion can come in handy here too, particularly if you sell a product that stores information/data.

For instance, QuickBooks urges you to subscribe before your trial expires in order to keep your expenses and receipts saved.

If you don’t upgrade your account, you risk losing this data and having to re-input it if you wait too long. For a lot of small business owners, that’s more than enough reason to subscribe to a paid account.

Tips for sending trial expiration emails:

• Send warning emails before the trial expires, and one on the day it expires.
• Show users what they’re losing by not converting now.
• The goal of these emails (particularly the final expiration email) is to get a conversion. So the only calls to action should be (1) upgrade their account (2) contact support with any questions.

Templates

Here’s a template for expired trials.

6. Discount/special offer email (optional)

Some companies like to throw in a last-effort to convert free trial users to paid customers. If you’re going to go this route, I recommend waiting to send this until after their trial has expired.

The last thing you want is to give a discount to someone who would’ve been willing to pay full price.

In this email, you’re going to give the user one last opportunity to sign up for your product. But this time, you’re going to offer them a bonus. It could be a discount, free upgrade or any other special offer that makes sense for your business.

This tactic can be helpful for early-stage startups when you’re just trying to get some initial users (and you’re tired of only seeing $20 MRR in your Baremetrics dashboard). But over time, you’ll probably want to avoid overly discounting your product.

Here’s an example of a last-chance offer email from Shift.

7. Feedback email

If none of the emails above are enough to convince someone in a free trial to convert, that’s ok. It happens.

Your product isn’t going to be the right fit for everyone. But you should try to find out why.

For users that didn’t didn’t convert, send an email asking why they decided not to subscribe. This does two things:

1. Gives you feedback you can use to improve your product.
2. Gives you one last opportunity to close them. If their reason for not subscribing is something you can fix, you can save the account. For instance, maybe they didn’t fully understand how to use your software, or they thought you didn’t have an integration you actually did have. Those are things you can address and get a new customer from it.

You can either have users reply back to your email, or setup a survey like this example from WP Stagecoach.

Tips for sending feedback emails:

• Make it easy for the user to give feedback. Either by replying directly to your email or a QUICK survey. Emphasis on quick. If they didn’t want to pay for your product, they probably don’t want to fill out a 10 minute survey about it.
• Keep the email short. No need to go on a long tangent explaining all the benefits of your product. You’ve had a handful of other opportunities to do that. At this point, it’s all about understanding what went wrong during the trial.
• Get feedback on your product and the trial experience. Your product could be a good fit, but if your trial experience sucks, it’s difficult for users to see the value of what you’re offering.
• Send this email 1-2 days after their trial expires. If you wait too long, they’ll more than likely skip over this email. Send it while your company is still fresh in their mind.

Template

8. Post-trial email

The trial period is over and they didn’t convert. Should you cut off all communications with them?

Not necessarily.

If they haven’t opted out of receiving emails from you, it’s a good idea to send a follow-up email to them at some point. Ideally, you’ll want to wait 2-4 weeks after their trial expired.

Here’s why this email is helpful.

There’s a chance that the user was doing a trial of several products at the same time. If they still haven’t found the right fit, it’s an opportunity for you to get back in the picture.

Plus, if you’ve made any improvements to your product since they had their trial, this is when you can tell them about it.

Here’s an interesting approach from ContentKing.

After your trial expires, they keep your data for a little longer and reach back out to you before they delete it. It’s a creative way to get in touch with un-converted trials and make one last effort to close the deal.

The wording is a little aggressive, but effective.

Tips for sending post-trial emails:

• Use this as an opportunity to regain lost opportunities. Let them know any updates you’ve made since their trial ended.
• Find out if they found another solution. If they had a serious need for a product like yours but didn’t choose you, they probably went with a competitor. A post-trial email is a good opportunity to find out who they went with and why.
• Offer to help them in any way you can. Just because your product isn’t a good fit right now, doesn’t mean the relationship is over. Offer to show them an alternative or help them solve their problem in a different way. There could be an opportunity to convert them later on, or even get referrals.

Template

Follow these best practices for free trial emails

I’ve given you a bunch of examples and templates to write free trial emails.

You could just copy/paste the templates and keep it moving. But keep in mind, templates are just that—templates. They’re meant to be customized to fit your business and use-case.

In order to help you get the most out of all these templates, here are some best practices to keep in mind when creating and sending free trial emails:

1. Personalize the emails

Please don’t skip this tip. Nothing says “this email is fully automated” like emails that start with “Dear user”.

Your emails should build a relationship with users and establish trust. How many people do you trust that don’t even know your name?

Beyond basics like a name though, you can dive deeper and personalize free trial emails with details like the plan the user signed up for or even what segment of users they are.

In our Messaging tool, you can send free trial emails to specific segments of customers based on anything from signup date to the source of the trial and tons of other filters.

The first is just a list of features, whereas the second touches on the tangible benefits users can get from those features.

If you want users to understand the value of your product, lead with benefits, not features.

3. Push users back into the product

I’ve signed up for trials of SaaS products, and throughout the entire trial period all the emails I receive are to get me to upgrade to a paid account.

No emails to teach me about how the product works. No tips to get the most out of the product. No educational content at all. Just “upgrade your account now”.

Like I mentioned, the trial is a chance for new users to try out your product. So doesn’t it make sense to use some of your free trial emails to encourage them to login and actually use your product?

If you’ve built a great product and it actually benefits the user, you shouldn’t have to beg or “force” people in-trial to pay for it. All you have to do is show them the value your product offers.

That’s why the bulk of your free trial emails should be about getting people in trial to become active users.

Up until your “pitch” email when their trial is almost over, the main call to action in your emails should be pointing users to log-in and use your product.

4. Be helpful

Take a look at your current free trial emails. Ask yourself, are these emails helpful to the user, or to myself?

The truth is a lot of marketing and sales emails are self-serving. And that includes free trial emails.

After all, you’re ultimately trying to get people in-trial to give you money. But what if instead of making it all about you, you focused on the needs of the trial user?

That’s why the first three emails I showed you don’t ask the user to upgrade their account. They’re strictly focused on helping the trial-user understand how to solve their problem using your product.

When you look at your free trial emails through that lens, it changes your approach.

Here’s an example from Beacon.

If you sign up but are inactive, they don’t send you an email begging you to upgrade your account. They send an email to figure out why you’re inactive.

This does a couple things.

For one, it prevents them from spamming inactive users. If people aren’t logging in, the chances of getting them to upgrade to a paid account are slim since they haven’t used your product yet.

Second, it gives Beacon information and context. They can find out exactly why people aren’t using the product so they know what to email them next..

We actually do something similar here at Baremetrics, using our own Messaging tool (sign up here if you want to give it try).

Here’s a look at how our email is set up.

In order to use Baremetrics, you need to connect a data source like Stripe or Braintree for example. If a user hasn’t connected a data source, we know they’re not really active. So we have an email that goes out to trial users who haven’t connected a data source.

First, we setup our audience in Messaging:

And then we wrote up an email that makes it easy for trial users to find out how to connect their data source.

Simple!

To do something similar, all you need to do is define an action users have to take to be considered “active”. I suggest making it an action beyond just logging in. Because there’s always a chance someone logged in once but never again.

For Beacon, that might be creating your first lead magnet. For us, it was connecting a data source. For a project management tool, it could be creating your first task/to-do item.

Once you decide what the action is, write an email that shows them how to do it and offer to help if they have any issues.

Start turning free trials into paid customers

Looks like all those free trials I signed up for paid off. Use the templates, examples and tips we went over to take your free trial experience to the next level.

Also keep in mind that your emails are only part of the equation. Converting free trials also takes an amazing in-app experience, top notch customer support and a product-user fit.

And if you’re looking for a tool to send your free trial emails, I highly recommend our Messaging tool. You’ll be able to plug in the templates we gave you and easily customize them.

Remember, every free trial is a potential new customer. Optimizing your trial experience (including the emails you send) is one of the strongest growth tactics any SaaS company can do.