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3 Copywriting Mistakes That Could Be Hurting Your Free Trial Engagement (And How to Fix Them Right Now)

Find a box with a CD-ROM in it, buy it, then learn how to use it.

That’s how I bought software as a kid. So when I first started working, I assumed that if I wanted to start using work-related software, I would have to pay for it the same way: upfront — site unseen! — just like the software of my youth.

I worried that I would have to justify the cost with only the specs, reviews, and sales guy’s word to make my case. (And if I was wrong, it would be my butt on the line.)

So I’m not exaggerating when I say that discovering I could try software for free actually improved my job performance and reduced new-on-the-job anxiety by ~62%.

Using a tool BEFORE I had to recommend it to my colleagues and pull out the corporate credit card gave me a chance to see which tools actually did what we wanted them to do.

All of a sudden, the risk that we’d pay for something that didn’t have a key feature or turned out to be a user-unfriendly nightmare shrank to almost zero.

What’s the Point of a Free Trial, Anyway?

Your serious prospects approach their free trials of your software with a mindset similar to mine circa 2000-something: they want to reduce the likelihood of buying something that doesn’t work.

They’ve got a problem to solve, they’ve discovered that your app might solve it for them, but they’re not yet certain that your app will be quite right. The free trial is a chance for new users to see for themselves what it’s like to use your app.

But. It’s not up to your free trial users to figure out how your SaaS app actually works. It’s not your new users’ job to figure out how your app will turn them into a better version of themselves.

It’s yours.

Too many SaaS apps lose free trial users with erratic, boring, or vague lifecycle emails.

If you run a SaaS app in pretty much any niche, you have an enormous opportunity to outmaneuver your competitors during the free trial process.

I sign up for free trials all the time to see how they onboard new users, and most don’t do a good job. Most onboarding emails don’t make it easy to understand what to do next. Most apps leave it up to me (the brand new user) to figure out how to get started.

Why is this a problem?

Because every time you make your new readers pause and try to figure out what to do next, you create an opportunity for them to give up and just do nothing instead.

What should you say to new free trial users?

Alas, there is no single hard and set rule. Every SaaS app is unique. What you say in your free trial, how you say it, and when you deliver your message will be specific to your app.

But if your biggest problem is that you’re sending triggered emails to new free trial users but they still aren’t signing back in after the first 10 minutes of using your app, there’s a strong chance that the copy in your emails is to blame.

To fix it, pull up your emails and see if they’re are suffering from one of these 3 engagement-killing mistakes.

Mistake 1: Your emails ask people to do too much.

When you offer more choices, you inspire less action.

The famous jam paper that explained the paradox of choice (and the TED talk that made it famous) showed us how we may be unintentionally taxing our prospects’ decision-making resources by offering too many choices.

But that’s not the whole story.

A 2015 meta-analysis of the research found that the total quantity of options is just one of many factors that can contribute to decision fatigue.

Another factor is the way that options are presented to us. When the presentation of options makes it hard to determine what choice is right for us, we’re likely to defer making a decision.

So if you’re sending your free trial users emails that look like this one, then there’s a strong chance you’re causing some serious decision-deferring choice overload.


It would probably take all afternoon to do everything this email mentions, and I might not get any closer to my goal.

This message tosses out 9 links (including one that’s hidden by my redaction) without a clear messaging hierarchy to help me figure out what order I should click on them.

This email provides login info, asks me to read help articles, watch help videos on 3 separate channels, ask for help via email, read interviews, or read a blog that might be helpful–all under the umbrella of “important information”.

But for your trial users, the real important information is the information that helps them decide what to do next.

The Fix: Write each email for the sole purpose of getting your users to complete a single action–and remove text and links that don’t support that action.

This particular message might be rewritten to focus on getting a single reader to respond to the important request hiding at the bottom of that email:


In the now-famous experiment, sending a welcome-why-are-you-here email helped Groove get response rates of 41% while also providing juicy voice of customer data to power future messaging development and laying the foundation for more personal relationships with new users.

Whether you’re following Groove’s lead or not, your free trial emails should all follow the Rule of One for best results: get one reader to take you up on one offer.

One email, one action. That’s it.

Mistake 2: Your emails don’t ask readers to do something specific and measurable.

When you rewrite your emails so that they’re focused on a single action, make sure that action is a discrete, clearly defined task on the user’s path to activation.

Your reader should be able to complete the task you’ve asked them to complete–and they should be able to tell that they’ve completed it.

Unfortunately, lots of emails offer vague and nonspecific CTAs. Some of them even sound exciting — especially CTAs that use the word “explore”. Exploring is fun! It’s adventurous! Brave souls explore!


Just because it sounds fun doesn’t mean it is.

All true of actual exploring. But your SaaS app is not the Louisiana Purchase.

When you ask someone to “explore” something — anything, really — you put the onus on the reader to figure out what to do.

And because exploring doesn’t have a clearly defined end, it’s impossible for your reader to figure out exactly what to do next–and when they’ve actually completed the thing you’ve asked them to do.

The Fix: Reduce cognitive overwhelm with a CTA that calls for readers to complete a clearly defined single task.

Zapier does this well. This app helps you connect what feels like an infinite number of apps to do all sorts of cool things (including powering the technical logistics behind managing your lead nurturing messaging).

With so many options, it would be easy for free trial users to get overwhelmed. They could explore their options, but then decide not to do anything.

So instead of leaving it up to new users to decide what to do next, Zapier’s first email removes some of the cognitive drain of “Shoot, how will I choose?” and offers a CTA tightly bound around completing a single task.


I love this email, and if I was going to rewrite it I would try other CTAs that don’t sound like they’re asking your reader to do work.

You already know what steps a new free trial user needs to complete to get to the point where your app suddenly becomes a can’t-live-without-it tool. You might even know the different steps different populations take to get to the point of activation.

Use your knowledge to guide your free trial users along the steps of that path.

Mistake 3: Your emails don’t connect the CTA to the outcome your free trial users want.

If you’ve rewritten your emails to get users to complete one and only specific and measurable action, that’s a great start.

Unfortunately, one of the most common grade-F CTAs I see in onboarding emails are the ones that don’t connect completing the action to solving a problem.

They make a call to action (the CTA “sign in” and its synonyms appear with devastating frequency), but they don’t make a call to value–so readers have no reason to expect that anything good will happen after they log back in.

Did logging into anything ever solve anyone’s problems? Of course not.

It’s what happens after you log back in that makes the difference.

The Fix: If your email’s CTA could easily appear in the free trial email sequence of another app outside of your category, change it.

If you’ve conducted your jobs-to-be-done research, you also know why your readers are using your app–and the outcome they hope to achieve.

Instead of “Log in to Your Account” or “Sign Back In Now”, your free trial email CTAs should make it clear that someone who clicks on this link will be moving closer to the goal they want to achieve with your app.

Buffer does a great job of sending an email that connects my click to what happens after the click.

After I signed up for a trial but didn’t finish setup, I got an email asking me to connect my accounts that also had some background info on what accounts, exactly, we’re talking about here. (In case I forgot what Buffer is.)


This email shows me everything I can connect to Buffer and makes it abundantly clear what I need to click to move forward.

Buffer could have sent an email that said “log back in” or even “connect a profile”. But “login” = boring and “connect a profile” = kind of vague.

Instead, this email makes it abundantly clear what to do with this email (click on the link that says “click here”) and the meaningful reason why you should take that next step (because it’s what you need to do to connect your social profiles).

Are You Making it Easy for Free Trial Users to Disappear?

When I first learned about free trials for software, I was over the moon. “Look at all this stuff I get to try!” “Look at all these opinions I get to form!” “Look at how few people I have to talk to before I make my decision!”

But what are all these thoughts really about?

What are your new free trial users really thinking when they sign up for your app?

My hypothesis is this: free trial users are really thinking some version of: “Look how little risk there is to trying this software. Let’s see if it works.”

The free trial reduces the risk of having to buy before you try. Your free trial messaging is what helps your prospect understand for themselves if your software will solve a problem.

What can you do to help free trial users understand that yes, your product can change their life?

Make it easier for free trial users to evaluate your app with focused, specific, and meaningful lifecycle emails.

About the Author: Alli Blum helps SaaS apps build messages that get customers. Click to get her copywriting checklist for high-converting SaaS onboarding emails.

  1. That first email — 9 different links — so overwhelming!

    Would love your input: what other CTAs would you try in that Zapier email?

    • Great question, Claire. Zapier’s email is one of a precious few that has a lot of the essentials already mastered, so now there’s an opportunity to experiment with ways to make an already great email even better.

      Because the word “work” sits right in the middle of the CTA text, one option would be to swap out “Build a Workflow” and replace it with something that makes the process sound easier. Another option would be to add click trigger copy to show that setting up a workflow doesn’t involve a ton of work.

      The reason that I’d start here is because I put off using Zapier for months. I assumed that getting set up would be just as complicated as manual workarounds or setting up my email marketing workflows. But boy was I wrong. The first time I used Zapier it took less than 15 minutes to set up my first Zap.

      Before making any changes, though, I’d listen to Zapier customers to see if my assumption about the work involved with “build a workflow” holds water and what objections or concerns they have before they get started.

      • Hey Alli!

        Thanks for the kind words and featuring Zapier. :)

        We’re actually in the process of updating a number of our emails. A rather big project actually, but I agree with you about the wording on CTAs. We definitely don’t want any action to feel like it’s going to be “work”! Even using the word “build” could be improved to sound less “work required”. Back to the lab to test!

        Really appreciate your input about how we can make the email more clear about how easy it is to get started. Will be taking that back to our team as we review these emails. :)


        Sean Kennedy
        Product Marketing @ Zapier

        • Hey, Sean!

          Rewriting your onboarding emails is definitely an enormous project. Not only do you have to think about the copy (for CTAs, subject lines, and body language), but you also have to think about how and why your customers use Zapier.

          There’s a lot to consider, but you already have a few things working in your favor. Zapier is a fantastic product and it sounds like you already have some solid ideas about how to take your emails to the next level (that’s a great point about the word “build”). Plus, you have an experimental mindset so you’re guaranteed to learn a lot along the way.

          Thanks for reading, Sean! Keep up the great work! :-)

  2. Sweet post, Alli.

    And you’re right, it’s not a new user’s job to figure out how to use an app. If you don’t send me good onboarding emails I’m about 98% guaranteed to not use your tool. And that’s even if I thought it was a cool idea, and would be useful in my life. We’re all just too busy to be adding more learning curves to our days :-).

    So when you’re working with your SaaS clients, what are you looking out for in their data to help you determine the best actions to trigger in emails? Do you find they usually know this or so they need guidance?


    • Thanks, Adam! I agree–the number of people who sign up for an app, can’t figure out how to use it, give up, and then find out a year later that it would have solved all of their problems must be staggering.

      There are 2 key data sets to consider. First, SaaS apps can look at the actions users take before they become a paying customer (this is the “what”). For example: if you have an invoicing software and you notice that more people become paying customers at the end of their trial once they’ve sent an invoice, then you can work backwards from the moment when an invoice has been to plot out the steps to get there. (i.e., set your currency, add a client, start a project, create an invoice).

      The second data set is the “why”, or the outcomes users are looking for. SaaS apps can look at what users say in support tickets, sales chats, and in reviews for clues about the outcomes customers want from taking those actions and then use that language (called Voice of Customer data) to write their copy.

      My experience has been that some SaaS apps know they need data and know how to use it–and others don’t. The Jobs To Be Done product development framework has helped a ton of founders figure out the real problems their apps solve for customers, but it’s mixed in terms of how many founders carry over the same approach in their messaging.

  3. Super post, Alli. My biggest pet peeve about onboarding emails is telling me to check out a feature without telling me why. What’s in it for me to learn how to use the feature your brand is crazy in love with? As you suggested, with a little research you can map features to the outcomes users want. And give users a more compelling reason to learn something new.

    • Thanks, Mary! That’s a great point. You hit the nail on the head when you said “what’s in it for me to learn how to use the feature your brand is crazy in love with?!” I couldn’t agree more.

      Users don’t want features–they want outcomes. So when SaaS emails (or a company blog) is just a list of feature updates, who cares? So what? When you ship a new feature, communicating how the feature solves a problem is just as important as the feature itself.

  4. Writing one-call-to-action per email is such a crucial step in getting these SaaS onboarding emails right. I get ones all the time that have six different call-to-actions, and I immediately delete them. We just met – why are you asking me to do so many things at once?!

    I think SaaS companies intuitively know it’s best to keep call-to-actions simple – but there is that looming pressure to send as little email as possible because email is “spammy.”

    It’s definitely worth noting that it’s better to send more email than overload a prospect cognitively with multiple call-to-actions in one email.

    • You’re so right, Sophia. I cannot count the number of times I’ve heard people say that they don’t want to “bug people” with too many emails–but then they go and bug people with a few emails so overloaded with requests that they’re objectively more annoying than multiple easy-to-react-to emails.

      I always cringe when I get emails that say, “just do these 5 things to get set up and then do these 4 other things to get started and when you’re done, tweet at us with one of these 8 hashtags.” In life and in email, it’s alway easier to do one thing at a time.

  5. Thanks for this. Interesting point you make about re-writing the Zapier CTA to make it seem like “less work” … it’s an area I think more SaaS companies need to go deeper on. I get that a new user has to put in some effort to see the value in an app, but the truth is, just signing back into a new app is almost always an interruption to what I normally do in the course of my day. If the CTA sounds like work (i.e., “Start your first project”) I’m likely going to feel like I’ll do it when I “have more time” :)

    • I think you hit on one of the biggest challenges SaaS apps face. In a perfect world, new users would sign up for a free trial at the moment when they’ve committed their time to actually use the app. In that world, they’ve already done all the other things that need to happen to “start our first project”.

      But since we don’t live in a perfect world, that’s one of the reasons why onboarding emails can be so challenging to write–you need to match the user’s state of awareness, understand what they want to do with your app, *and* find a CTA that actually make sense in the context of what they’re doing when they sign up for a trial. If it feels like getting started is going to be an inconvenience, then we’re more likely to do nothing.

  6. I love this, Alli. You’re 100% spot on.

    Definitely strikes a chord with me. I used to work in sales and we’d do product demonstrations for customers regularly. It was great because we could show them what to do and how to use the product best suited to their needs.

    The problem SaaS faces is that, because it’s Saas, all of the trials are completely self-directed by the user. Which is…not ideal from a sales standpoint. Making it easy for the user to decide what to do and how and figure out how the app works is key, and you’ve spelled that out really nicely here. Great work!

    • Thanks, Katie!

      You’re absolutely right. For customers who don’t always want to talk to people during the buying process (ahem), a free trial is great precisely *because* it’s self-directed. But when SaaS apps don’t replace that one-on-one call with some other way of helping new users get started with the app, you’re right–it’s not ideal.

      You also hit on another point that I didn’t explore in this post (but hopefully will in another) which that it’s so important to target free trial messaging based on who your prospects are and what they want to do. One size doesn’t fit all in automated messaging any more than it does in a one-on-one call.

  7. Great, thoughtful post! Your mistake #3 is the one I see all.the.time. And it’s frustrating, especially when there’s so much room for improvement.

    Your free users want to know the next step in that call to action. It’s like: “I want a solution in my life thanks to your SaaS app, but you can’t even express what my next action looks like? Gah. Next.”

    • All.the.time, indeed, Laura. “Sign in” and “Log in” are some of the most common CTAs for free trial emails. It pains me every time I see one because it’s the low-hanging fruit of copywriting fixes but still so common.

      For me, it’s also one of the CTAs that most expresses work. “Sign in” makes me wonder, “Will I have to use my password to sign in? Shoot…what’s my password? Do I have to reset it?” And without that clear expression of what’s going to happen after that hassle, so many free trial users mutter “Gah. Next.” and move on.

  8. Great article Alli!

    I don’t have SaaS clients, by just about every ecommerce client I work makes Mistake 2: Your emails don’t ask readers to do something specific and measurable. and their engagement suffers as a result. I can’t wait to back up my requests, that customers make sure they ASK clients to do something specific in their emails, with your article!

    • Thanks, Christine!

      You’re so right. I get a ton of ecommerce emails that show me pretty pictures but don’t actually ask me to do anything…so I don’t do anything. I’m glad to hear that this post might help you back up with your requests–if you end up using it, let me know how it goes!

  9. Awesome post, Alli! My favorite part is on the need to reduce cognitive overwhelm. SO key. Crazy how in real life, we have such an organic sensitivity to causing overwhelm but so many of these every-day…mannerisms, for lack of a better word…get lost in print.

    • Thanks, Hannah! You’re definitely right. The sensitivity many of us have during face-to-face conversations doesn’t always translate to written communication, and I think it’s partly due to the medium. Since we can’t see the person we’re talking to over email,
      we can’t pause to let our conversational partners ask questions if we see a confused expression on their face. That’s one of the reasons why it’s so important for emails to make it easy for people to understand what to do next.

  10. Love the post! My clients don’t do free trials but this info is tremendously helpful nonetheless. Keeping your tips to three makes it easy for anyone to remember!

    I love the Louisiana Purchase line in reference to “explore” on buttons. Now I have something clever to add — in addition to “you’re making it tough for the reader.”


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