Are Your Free Trial Emails Making You Look Desperate? Here’s How to Fix That

A SaaS free trial starts like any relationship – full of hope, dreams and possibilities.

Your prospect starts a trial and gladly opens your welcome email.

She wonders what marvellous, mind-reading revelations she’ll find in your onboarding sequence. (“Please let this be the product that gets me!”)

But then… she takes a moment or two away from you. Other commitments take priority. Although she likes your product, she’s forgetting about you – she’s not sure you’re The One. Plus, her friend just started seeing this other SaaS product, and she’s all “It’s sooooo beautiful” and why should she get a beautiful UI? Suddenly your “rich with utility” app isn’t quite so appealing. I mean, it’s a nice product, but it doesn’t make her eyes all 😍.

She’s losing interest in you.

She hopes you’ll just kinda go away. In a week or two, communication will cease. It’ll be like you never even met.

But you’re not gonna let her go so easily. After all, she was into you, like, two weeks ago. Maybe she just needs to hear from you more. So you start:

  1. Internet-stalking her with retargeting ads
  2. Pushing messages at her friends and social network followers
  3. Sending her passive-aggressive don’t-leave-me emails like this:

Desperate, right?

The two of you only saw each other briefly. What’s all this “fall in love” talk?

The 2 Act-of-Desperation Mistakes SaaS Teams Are Making with Free Trial Emails

SaaS teams believe a trial signup equals a storybook romance.

They want to solve your problems and encourage you to date them take the right step to grow your business. SaaS businesses aim to win your love and affection by giving giving giving giving. Because giving is good, right? Users like it. They keep saying they like it.

Nobody stays with you because you’re a big ol’ giver. Yet SaaS teams do all this giving. And 90% of their trial users dump them.

desperate saas marketers

Without a word of explanation. Just… dumped. 

After working with dozens of startups on their email copy, here’s what I’ve identified as the core of what SaaS marketers are getting wrong.

1. Interest ≠ Infatuation

For some reason, SaaS teams are counting on the idea that a new user went into a sealed room with their free trial for 15, 30 or 60 days, and in that time they fell madly in love with the product. 

If The Bachelor taught us anything, it’s that even a sealed room can’t create love.

Except real life is not a sealed room.

The reality is your free-trial user signs up for a trial… and then heads back into a massive, endlessly explorable digital and physical world, filled with rock-climbing classes and sangria-on-patios and deadlines and Facebook and existing processes and people and shiny distractions and shitty distractions. Within minutes of signing up for a free trial, everyone but the most insanely passionate trial users (who require almost no work to convert anyway) will go off and do something else. That’s a problem.

2. And the solution isn’t in your data

Startups look to the data! Growth-stage businesses look to the data! Everyone looks to the data!

But when you do, you don’t find answers. You find that your funnel is, depressingly, more of an inverted pyramid than a wide-mouthed funnel. Your cohort analyses are… sad. All the data sliced all the ways leaves SaaS marketers like you scratching ye olde head, wondering what’s wrong and how to fix what’s wrong.

Because here’s the thing: your trial users are interested.

But here’s the problem: SaaS companies have yet to crack the nut on how to convert interest into 1) activation, 2) revenue and 3) retention.

And while you could try other things, emails are your least expensive and most reliable option. I’ve seen them in action. And the fixes are simple enough that you should address your emails immediately.

So here’s how to make your free trial emails turn interest into infatuation into income.

First: Accept that your free trial emails, as they are today, are almost certainly chasing away money

When I first started consulting, I considered using a CRM to keep track of my leads. So I signed up for a free trial of Pipedrive to see what it could offer me vs. using email.

And the welcome email wasn’t the best I’ve ever received, but I was hopeful Pipedrive could help me organize who was in my client pipeline.

(Sidenote: Pipedrive is just an example. Nothing but love for their team!)

Check out the welcome email they sent me:

The webinar sounded good.

Was it actually good? I dunno – I didn’t end up going to it.

Life got in the way. Plus, I couldn’t get Pipedrive to work with my inbox without upgrading to a paid plan. So before I knew it, I hadn’t learned a thing about Pipedrive, I hadn’t started using it, and my free trial was ending. As my free trial came to a close, they sent me the email I mentioned above. Here it is again:

Let me pause for a moment to scratch the surface of the problems with that email:

  • Can we get a name in there? You know my name. I used it to create my account. You should use it to talk with me.
  • That’s your opening line? Really? “This is just to remind you.” Ugh.
  • Q: “Want to continue with Pipedrive?” A: Nope.
  • Only using voice at the bitter end of the email…

So, sure, something like 50,000 people are in love with Pipedrive. Those folks converted in spite of that email. Congrats to Pipedrive.

But because you and I care a great deal about converting more trial users, let’s work on writing a better email.

And let’s start by stepping back a bit…

Behind the scenes of selling software (before the cloud)

Before the Internet, you had 2 ways to buy software.

  1. If you were a consumer, it came in an unwieldy box from an electronics superstore like Circuit City (RIP!). Not much salesmanship there.
  2. If you were a corporation, you had a designated sales person who got you to sign a multi-year contract. Meaning an individual could assess a company’s particular situation and use various tactics to get the sale.

Then web-hosted apps became a thing. And companies realized they could make more money if they charged customers on a subscription basis. Now users could access apps anywhere, as long as there was a browser and an Internet connection. Meaning companies could cut down on the costs associated with packaging and commissions to retail stores. And take home at least 60% of the gross margins. The venture capitalists showed up in droves.

But even before the cloud and free trials, the practice of giving away software for free has always been very popular. The only difference is the delivery mechanism. Remember the days of AOL CDs in your mailbox?

giphy 1

Seriously, how much did AOL spend on direct mail?

The marketing strategy for software has stayed constant, unfortunately. And here it is:

Hook users with a free sample, with the hope they like it so much they buy the full version.

Drug dealers have a similar marketing strategy. There’s just one difference. Drug dealers don’t hope you’ll like their product. They know.

Hope is a dangerous thing

The SaaS marketer’s strategy is filled with hope.

Hope is what you defer to when you can’t science the shit out of something. Hope is what you defer to when you don’t know what you’re doing. Hope kills businesses, ends sales, frustrates marketers – and frustrates prospects. Hope isn’t for closers. Yet it’s at the core of your acquisition strategy.

SaaS marketing isn’t hope marketing – those free trial emails have gotta close the sale

Consultant Alan Weiss describes four reasons someone might NOT buy your product:

  1. No need – “It’s a neat tool, but it’s not necessary for what I’m trying to accomplish.”
  2. No money – “I can’t afford it because I’m a startup” or “I have too many other financial commitments more pressing than yours.”
  3. No urgency – “This problem you’re solving for me is necessary, but it’s not my top priority right now.”
  4. No trust – “I don’t believe you have my best interests in mind.”

Weiss is talking about winning six-figure management consulting contracts, but he claims it works for any product or service you’re selling. And he admits to flying halfway across the world to close a deal if it means overcoming one of these objections. Few SaaS startups are in a place to fly eight time zones over just to close a deal. I mean, you’re selling an app for $25/month.

Instead of frequent flyer miles to solve your conversion problems, you’ve got basically 2 things: a name and an email address. You’ve gotta work with those 2 resources – and not much more.

So here’s a killer opportunity you may not be leveraging as much as you could.

It’s the Trial Ending email, and here’s how you can make it rock.

Here are 3 easy steps to close better with your free-trial-ending emails

To persuade trial users to pay for your SaaS product, you should use the trial-ending emails to:

  1. Emphasize what the user will miss out on by not upgrading to paid.
  2. Contrast the outcomes of upgrading vs. not upgrading.
  3. Provide a single call-to-action.

Here’s what I mean…

1: Emphasize what the user will miss out on by not upgrading to paid

There’s nothing that motivates people more than telling someone what they’ll miss out on. In psychology, it’s called loss aversion.

So ask yourself:

What will users miss out on if they don’t upgrade to a paid plan?

To give you a few ideas, think of the key features in your product. But instead of naming them off in the email, turn them into benefits that change the way the user was doing something before.

The benefits of the feature should outweigh the cost of the product. And be painful enough that a user has to stop and think, “Will I miss out if I don’t grab my credit card?”

To demonstrate, let’s look at this email promoting Sumo Pro. Although a cart abandonment email, Sumo does a good job of telling me what I’ll lose if I don’t buy Sumo Pro soon.

Notice how Sumo stacks the benefits of upgrading to the Pro plan. They could have just said I’ll miss out on the heat map features. Instead, they point out that without Pro, I won’t know how engaged visitors are on my website.

And if a prospect is using their website as a way to capture leads…they’re likely to believe Sumo is THE solution to their conversion problems.

Plus, there’s nothing like a 10% discount to entice on-the-fence users to sign up in the next 24 hours. Not necessary, but it’s something extra for the user to lose out on.

2: Contrast the outcomes of upgrading vs not upgrading

Mid-century ad executive Rosser Reeves (creator of the value prop!) was finishing up lunch in Central Park with a friend. They came across a homeless man sitting on a bench with a sign. The sign read:

“I am blind.”

Reeves bet his friend that he could make the homeless fellow more money by changing the words on his sign. With his revisions, the sign now read:

“It is springtime, and I am blind.”

The result? The homeless man’s panhandling success increased and Reeves won his bet.

But why?

Sometimes missing out on benefits isn’t enough. It might be a proven fact that your product’s feature has helped others. But sometimes it’s not enough to persuade the skeptical trial user. So you need to change their mindset. You need to illustrate what would happen to the user if they choose to pay for your product… and how life would be if they didn’t.

It wasn’t enough for prospects to know that the homeless man was blind. After all, only a few of them dropped coins into his bowl.

But because Reeves mentioned springtime, prospects suddenly realized the homeless man couldn’t see the blue skies, the sunshine and blooming flowers in Central Park. And for that reason, they were compelled to give him money when they would have ignored him.

Here’s how to use contrast in your trial-ending email

To apply this in your trial ending email, consider how your product can transform your user’s outlook on business… or how terrible their life would be without your product.

Or in the words of Aaron Orendorff, ask yourself one of the following questions:

What heaven will this email deliver my subscriber unto?


What hell will this email save my subscriber from?

For example, here’s a trial ending email from Honeybadger, an error monitoring service for Ruby apps.

It’s cool that Honeybadger logged 220 error notices. But think about why engineering teams bother with error monitoring in the first place.

Plus, reminding the user that they now have to pay to track bugs? Come on. There’s so much hell this app could save a user from! Though the majority of software errors are a nuisance, there are ones that are downright catastrophic.

 Let’s look at the version I rewrote below.

Any software developer worth a damn would do their best to avoid writing buggy software. Plus, an unscheduled meeting with high-level managers to discuss how your work caused weekend profits to plummet? If that’s not your idea of hell, I don’t know what is.

3: Provide a single call-to-action to upgrade

What’s the next step a user needs to take to upgrade from trial to paid?

Dan Pink calls this an off-ramp. You may recall Pink’s study of a college food drive: explicit directions prompted more donations from groups of individuals who had never donated to a food drive than groups of people who had a history of giving.

Translation? You can convince the most resistant people to do something if you make it clear what it is that you want them to do.

Mulesoft’s trial-ending email doesn’t make it clear what I should do next. Take a look:


  • My trial is over. If I wanted to watch a webinar, I should have seen it before this email.
  • Now you want me to read a case study?
  • I have to talk to a human being to extend my free trial? Pass…

Compare this with DocuSign’s email, where it’s obvious what they want me to do: Upgrade my account.

And they do an excellent job of reminding the user what they’ll miss out on, which is making it easy for others to do business with them.

Think about the number of steps your prospect has to go through to convert / actually pay for your SaaS. If you add six links to your email asking the user to do different things, they’re going to get confused. And maybe start to wonder if paying for the product is the right thing to do. And while gaining Likes on Facebook or Follows on Twitter might be a nice-to-have… your goal is to move that trial user into a paying customer – so don’t lose sight of that.

Two Ways To Get a Response From Passive Trial Users

What about those trial users who don’t convert even after you’ve optimized your trial-ending email copy?

Keep in mind that these non-converters have already spent time interacting with your app in some way. They have an opinion. If you’ve written the most persuasive trial ending email and they STILL haven’t converted, send them a trial expired email.

Here are two ways to go about it:

  1. Ask for advice.
  2. Get them to do something (that doesn’t require money)

Lemme show you now.

1: Ask for advice

If you never ask, you’ll never know what keeps your prospect from buying, and you’ll never figure out their level of interest.

According to Robert Cialdini, if you ask a person for advice on what you could do better, it puts them in:

“A merging state of mind, stimulating a linking of one’s own identity with another party.”

Translation: If you can get a person to think about the ways they would improve their business, it creates a bond. The bond may not result in becoming a paying customer, but you could possibly win them over by other means.

When free trial users finish up with Autopilot, Autopilot initiates a customer feedback survey that is explicit about how long it takes to complete: 60 seconds.

Thanks to this study, Autopilot found out:

“27% of our expired trialists don’t buy because they’re still evaluating their options. Us asking both nudges them back into the product and gives us insight into conversion barriers. It’s a win-win.”

A 60-second survey might not solve your business problems, but it can give you the motivation to undertake more in-depth customer research. If you want a technique for that, take a look at the Jobs-to-Be-Done framework.

2: Get them to do something (that doesn’t require money)

So what if they didn’t buy right now? It doesn’t mean they will never buy it. There are plenty of no-cost ways for them to engage with you, too. Neil Patel suggests other forms of action, like reading a blog post or replying to an email.

The call-to-action doesn’t always need to be Upgrade Now. But it’s important to get the prospect to commit to taking smaller steps that could lead to an eventual purchase.

Ruben from Bidsketch does this by sending blog content to his free trial users who don’t end up converting:

Bidsketch might not be the proposal software solution for you right now, but they want you to become a better entrepreneur. So go on, read their blog post on emotional intelligence. The more you read from them, the more you might grow to like them – and people ultimately do business with people (and businesses) they like.

How to fix your 90% free trial failure rate

You could have all the ad money in the world and still trying to figure out your trial-to-paying conversion rate – when all you may need to do is rewrite your trial ending emails.

It’s a no-brainer task that you can knock out within a few hours of reading this. To recap, here’s what to add to your writing to-do list…

In your trial-ending email, be sure to:

  1. Emphasize the benefits the user would miss out on.
  2. Contrast the outcomes.
  3. Provide a single call-to-action.

For your trial-expired email, you can:

  1. Ask them for advice.
  2. Get them to do something else (that doesn’t require money).

And keep this in mind: If users sign up for your trial, there is a little part of them that wants to make your product work.

So choose your (email) words wisely. Because it could be the thing keeping your SaaS product from turning interest to infatuation to income.

~Sophia 🙂

About the author

Sophia Le

Sophia Le helps SaaS companies grow customer relationships with email. Visit her website for 7 free fill-in-the-blank email templates and follow her on Twitter.

  • Austin Page

    fantastic read. thank you!

  • Sarah Lee

    very helpful! thanks for sharing this!

  • Erika Pena

    Winning people’s “love and affection” can be a challenge, as marketers, creating that hook can determine the success of the business. You make great points in your article. One needs to fill those needs customers might have, by offering and pointing out how they can benefit from your product/service. Ignitur is a SEO reporting software solution that addresses the common pain-points most web marketers share. It’s not easy but you don’t have to go in blind.

    • Sophia Le

      Thanks, Erika! I agree with you completely – emails help us win over a user’s love & affection, but ultimately that “hook” takes a lot of work to find. You can make a guess, but it requires a lot of customer research and introspection to find it.

      And Ignitur sounds cool – I’ll have to check it out.

  • It is a great article !Thanks for sharing useful information…………..

    • Sophia Le

      Thanks for the comment, Stewart!

  • Great article Sophia. Very interesting topic. Lots of meat in here. Thanks for sharing!

    • Sophia Le

      I’m glad you think so, Emmerey. And you’re welcome!

  • Amy Posner

    Sophia – Great article – your insights along with the examples make it crystal clear that most companies are not focusing on the benefits for their users, but instead, are sending thinly veiled messages that scream “we have no clue what you care about!” Infatuation to income – love it!

    • Sophia Le

      So true, Amy. I’d even say these emails scream “We are too backed up with other priorities to find out what you care about.” Glad you enjoyed it!

  • Gisele J Grenier

    I’m seeing some really good things in this article that I can apply to my own business which is teaching art lessons via a membership site. The current tech I’m using doesn’t allow for trials with an end date, changing that tech this month and will definitely apply what I learned here. Thank you!

    • Sophia Le

      Awesome, Gisele! There are definitely lessons to apply to any subscription-based service. Good luck on the tech change 🙂

  • Great article Sophia! Thanks for sharing all of this with us 🙂
    Sidenote: The skillshare link in your author bio doesn’t work. – leads to 404

    • Sophia Le

      Hi Roland, it’s fixed now! Thanks for the comment and the heads up 🙂

  • Hannah

    Love this Sophia! Especially the Rosser Reeves “I am blind” example. I also really appreciate how you broke down the problem with trial emails and your solution. Emails can be kinda intimidating aka easy copy to put off, but your article really helps make the fixes feel waaay more tangible and doable. Thanks!

    • Sophia Le

      You’re welcome, Hannah – thanks for reading! Isn’t that Rosser Reeves story crazy? If only all homeless people had him to help with their signs…

  • Awesome stuff Sophia!

    • Sophia Le

      Thanks a bunch, Sasha 🙂

  • AlliBum

    Great post, Sophia. I loved how you put this: “SaaS teams are counting on the idea that a new user went into a sealed room with their free trial for 15, 30 or 60 days, and in that time they fell madly in love with the product.”

    Also, excellent storytelling skills at work in the Honeybadger rewrite. I didn’t know what Honeybadger was before this post and now I’m pretty sure I need it–and I’m not even a developer.

    • Sophia Le

      Thanks for the comment, Alli! The larger issue at hand is SaaS company shouldn’t always bank on that 15, 30, or 60 day free trial to hook users. And if they do…they better do something to close the sale beyond sending a few lovesick desperate emails.

  • This is awesome stuff.

    *Goes away to modify trial expiry emails*

    • Sophia Le

      Ha! Should I ask what was in your original trial expiration emails, James?

      • Heh… well… I hadn’t actually checked the default template for the gateway, just switched on the email. Inserted below.

        One of the templates even referred to our product as “ABC”, which I hadn’t changed 😂

        Luckily every Thursday I find an email to improve. I know what this week’s is…


        Your free trial period expires on {{subscription.trial_end}}. At the end of your trial the subscription will be cancelled.

        Please upgrade to a paid subscription plan to continue using our services.

        If you would like an extension on your trial, please email us and we will be happy to accommodate your request.

        To add or update your payment method information before your trial ends, please login to your customer portal account using the link below:

      • Sophia Le

        I’ll give you a pass on this one! Just…add some personality into it.

        As if I haven’t given you enough to do…😛

      • Yesterday I wrote a whole new trial expiry warning, expiry and follow up a few days later, along with a survey. Looking forward to see how it goes. Thanks so much Sophia!!

  • Lisa Burns

    Getting ready to launch my first product at the end of July. This advice couldn’t have come at a better time! Love all of the fantastic examples. I’m already busy sketching out a few templates for later use. Thank you!

    • Sophia Le

      You’re welcome, Lisa….good luck with your product launch! I know you’re hard at work creating your own templates, but let me know if you need more. I have a few of my own 🙂

  • Christine Given Laureano

    If Honeybadger doesn’t listen to your advice, they’re crazy! Sophia, this is a killer article and not only on point for Saas, but as I see it, anyone using email and a digital or ecommerce platform should take your advice, not only for onboarding, but also for customizing those dreadful abandoned cart emails. (Great examples by the way.)

    • Sophia Le

      Thanks a ton, Christine! There is definitely crossover between trial ending and abandoned cart emails. Both types of emails need to walk the line between emphasizing loss and highlighting contrast…without sounding so eager.

  • Marny Harksen Bassett

    Sophia Le to the rescue! This post came at the nick of time—and saved my butt! I was just about to send off a string of “we wantcha back” emails for my client. Rewriting the campaign is going to take some extra time, but your examples prove that the decision is a no-brainer. Huge thanks.

    • Sophia Le

      Marny, I’m glad I could help. Let me know if you want a second set of eyes on the new email campaign!

  • Loved reading this and the examples. So many emails seem to get stuck on processes that they become cold and ineffective. I loved how the good examples had personality, clearly listed the benefits (or losses) and had a clear call-to-action. There’s a ton of potential in optimizing the copy of these emails. More companies should take advantage of the opportunity to do so. Thanks for the post!

    • Sophia Le

      I agree, Steve…it’s such an easy fix for increasing the trial-to-paid conversion rate, I’m surprised most SaaS companies ignore doing it. It may be due to the fact that “writing emails” is just another task for the marketing team, or even worse, the engineering team during a software launch. Thanks for reading!

  • HUGE fan of asking for advice! After some reflection, I’ve concluded that my most helpful, substantive relationships with customers have come from asking for suggestions or posing the question “How could we do better?” The folks who take the time to write or call back REALLY have something they want to say. They care. They immediately shoot to the stratospheric VVVIP club on my list.

    I guess this could fall under the troublingly-vague umbrella term User Engagement, but that just seems so flaccid and apathetic. Passionate people have something to say, and they tell you when you ask (a LOT more frequently than when you don’t ask).

    • Sophia Le

      Thanks, George! From a data point of a view, there is a chance of voluntary response bias so you might get the strongest opinions from your user base.

      But you also have the chance to swipe great copy from their responses, or inform your product team of how a prospect is using your product, in a way you’ve never thought before. And for that alone, it’s worth sending that one email.

      • Agreed — their objections or concerns fuel sales page copy. Their questions turn into FAQs and blog posts. Their use cases *might* turn into a whole new marketing campaign. The responses you get are a cornucopia of insights that leave me feeling invigorated — somebody out there cares almost as much as I do!

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