10 Steps to Create a Winning Free Trial Marketing Strategy

10 Steps to Create a Winning Free Trial Marketing Strategy cover

Having a solid free trial marketing strategy is crucial to product growth. That said, converting users into paying customers after their free trial period ends is easier said than done. In this article, we’re going to show you exactly how you can build a reliable free trial strategy to convert free trial users!


  • A free trial user is more likely to convert than a cold lead because they’ve expressed enough interest in your product to actually sign up and invest time into exploring its features.
  • There are five growth strategies to choose from before you can begin your free trial marketing campaigns.
  • You need to create user personas (either based on existing users or target customers) to ensure that your free trial marketing feels personalized to the demographics that you’re aiming for.
  • Choose the right features to add to your free trial to ensure that users are able to solve their problems without losing the incentive to upgrade to a paid plan altogether.
  • Implement in-app messaging and contextual onboarding to reduce the time-to-value for trial users.
  • Use product analytics to identify the stickiest features and use them to convert more trial users into paying customers.
  • Tying email and content marketing into your free trial marketing strategy can provide a more holistic omnichannel marketing campaign.

What type of marketing is a free trial?

Offering a free trial period is a great way to acquire new users and get them to try your product. Once they recognize the features and benefits of your product, they’ll be more likely to become paying customers.

The average trial-to-paid conversion rate is 25% in SaaS, but it can vary depending on other factors, including the efficacy of your product-led marketing strategy. Here’s how you can calculate your own trial conversion rate:

conversion rate free trial marketing strategy

Why is a free trial effective in marketing?

In addition to getting new users for your product, there are a few other benefits that you could reap by adding free trials to your marketing strategy:

  • Low cost: Free trial marketing is one of the most cost-efficient strategies that your company can implement. Despite the low cost, it offers a lot of value to every potential customer that lands on your page.
  • Reduced time to value: Instead of having to go through a long deliberation process and make a lasting commitment, a free trial lets new users experience the value your product provides within a shorter period of time.
  • Higher-qualified leads: Free trial marketing offers a big advantage since it only brings in active users that are genuinely interested in giving the product a try. This will increase the ratio of MQLs and SQLs compared to other lead generation methods.
  • More conversions: Since free trial users are more qualified leads, giving them hands-on experience with the product is likely to lead to higher conversion rates. This, in turn, drives down your customer acquisition cost.
Marketing and sales funnel SaaS

How to create your free trial marketing strategy

A good free trial model (and any customer-oriented marketing approach) needs to be tailored to your company’s growth strategy, audience, and go-to-market strategy. Here are 10 things to consider while building out your free trial marketing strategy:

  1. Finding the optimal growth strategy
  2. Defining your target demographics/audience
  3. Setting trial length and credit card requirements (or lack thereof)
  4. Selecting the right features
  5. Reducing the time to value
  6. Implementing strategic in-app messaging
  7. Engaging trial users through email
  8. Leveraging urgency to increase conversions
  9. Looking at product analytics to identify opportunities
  10. Running post-trial feedback surveys

1. Pick your growth strategy

Tony Ulwick’s Jobs-to-be-Done Matrix outlines five main growth strategies. The theory is built on the premise that new products or services will only succeed if it does the job better, does it for cheaper, or both.

Jobs-to-be-done growth strategy matrix

Here are the five growth strategies from the JTBD matrix:

  • Differentiated strategy. The first — and seemingly most logical — approach is to do the job better than competitors and charge a premium for it. Underserved customers won’t mind paying you more if you can get the job done better.
  • Dominant strategy. If you want to win all types of customers — both underserved and overserved — then you need to get the job done better while charging less in the process. This can be difficult for startups or early-stage SaaS companies to achieve.
  • Disruptive strategy. If you’re in a red ocean market with big players offering expensive, full-suite products, then you may need to adopt a disruptive strategy. Narrow your product’s feature set, charge less for it, and land overserved customers.
  • Discrete strategy. Getting the job done worse yet charging more often works out well. However, it could work well in market spaces where competition is sparse, and customers have limited options.
  • Sustaining strategy. Introducing a product or service that’s ever so slightly cheaper and does a marginally better job is known as a sustaining strategy. This is ideal for companies that want to grow slowly rather than disrupt or dominate their industry.

Which go-to-market strategy you choose will depend on how complex your product is, how much it costs, your preferred marketing strategy, and whether or not you’ve already achieved product-market fit.

Product-market fit free trial marketing strategy

2. Define your target audience

Regardless of which growth strategy you adopt, it won’t produce the results you’re hoping for unless you have a clear understanding of your target audience. Depending on how long you’ve been in the market, you have two options:

  1. Create your ideal personas based on your existing customer base
  2. Create your ideal personas based on the type of customers you’d like to attract

In either case, your marketing team and sales team should use closed-loop analytics to compare data. Customer analysis only works when you have a holistic view of the data — otherwise, you won’t be able to create an accurate ideal customer profile (ICP).

To ensure that your marketing messaging, free trial onboarding, and product experience are as personalized as possible, you should divide your audience into multiple segments. Here’s a quick look at how it’s done on Userpilot’s user segmentation dashboard:

User segmentation dashboard Userpilot
User segmentation with Userpilot.

3. Plan the details

Now that you’ve selected the right growth strategy and nailed down your target audience, you can start planning the details of your actual free trial. The first thing you’ll need to decide when it comes to offering free trials is the free trial length.

In general, complex solutions or a niche product with a smaller total-addressable market would benefit from longer trial periods because the core features take longer to understand, and there are fewer potential customers available.

Of course, product demos are a good way around this. You could create demos that highlight key features from the get-go to help free users figure out what to focus on. You can also send a “free trial ending” alert email 5-7 days before the trial ends so inactive users get a reminder to try any features they’re curious about.

Userpilot demo as free trial marketing strategy
Sign up for Userpilot’s live demo.

Another thing you need to consider is whether or not you’ll require new users to provide their credit card details upon signing up for the free trial. The free trial conversion rate tends to be higher when you require credit card information, but the initial number of free trial signups might drop.

Beyond credit card details, you should also be smart about what information you ask for on your free trial signup pages. Start with the most important information to identify the user’s goals, then rely on progressive profiling to fine-tune the experience over time.

Notion free trial marketing strategy
Notion’s sign-up flow.

4. Integrate the right features

Building out the right feature list for free trials is one area that most SaaS companies struggle in. There are two basic approaches that you can take:

  1. Limit the free trial’s feature set to incentivize an upgrade
  2. Include the entire feature set to show active users your product’s full potential*

*You’ll likely find the number of free trials rises if you include the full feature set AND don’t require credit card information since the same users may sign up for multiple trial periods using different email addresses.

Slack takes a hybrid approach by giving access to most of its features but limiting the number of seats. When deciding on the free trial feature list, be sure that the product will be able to cover all primary customer pain points (but you can save secondary pain points for paid users).

Slack free vs paid plan
Slack’s free trial vs. paid plans.

5. Reduce time to the Aha! moment

If your usage data is telling you that semi-active users aren’t discovering all the features during the course of the free trial, reducing the time to that Aha! moment is crucial. While it’s true that users probably already had an Aha! moment upon signing up, it doesn’t stop there.

It isn’t until the user realizes value within the product itself that you’ll have a chance of converting them into a paying customer. Adding step-by-step guides to the onboarding process can speed up product adoption and reduce the time-to-value.

Once a new user has their first Aha! moment, you should start following up with more tips and continue distributing information to give them a constant sense of progress. The easiest way to do this is through in-app messaging, which brings us to our next point.

User journey Aha moments SaaS

6. Strategize in-app messaging

You can’t just send randomized messages to users and call it a day. A truly effective in-app messaging strategy should include interactive flows that guide customers, in-depth guides that help them understand your SaaS product and upsells from your marketing department.

A few ways you can use in-app messaging include teaching users how to navigate the interface, adding tooltips about specific features, or other UX patterns that highlight specific product capabilities which provide value for their use case.

Your in-app messages need to be well-timed, contextual, and displayed in the optimal sequence. For instance, an onboarding checklist will be much more effective when combined with other elements, such as welcome screens, rather than treated as an isolated element.

In-app guidance UI patterns SaaS
Userpilot’s UI patterns for creating in-app flows.

7. Leverage email marketing to strengthen communication

Email communication makes it possible to stay in touch with users throughout the most critical parts of their customer journey and offers additional resources that you weren’t able to include in your in-app messages.

Creating a win-back campaign can also leverage email messages to bring back unengaged users before their free trial ends. You could even consider offering their first year at a lower price or having a real person follow up to see why they haven’t been engaged during the free trial.

If you want higher conversion rates, then you could even try having the company’s founder send out welcome emails to users who sign up for the free trial. This, paired with a clear call-to-action, can work wonders when trying to acquire new customers with free trial marketing.

Other essential email types include free trial expiration, trial extension, and feature highlight emails. These types of emails can make closing sales a lot easier in the long run.

Here’s an example of a contextual welcome email that Calendly sends to new users:

Calendly free trial welcome email
Calendly’s free trial email.

8. Add a bit of urgency

Because of how big a commitment subscribing to new software can be, SaaS companies know that a sense of urgency is essential to user acquisition. You don’t need to be pushy about it, but sending trial expiration reminders through in-app messages or emails can go a long way.

The last few reminders could even be paired with a special offer that compels trial users to sign up for a paid plan or even upgrade to a higher price tier. Here’s how Squarespace uses urgency and action-based CTAs to nudge users toward the next step:

Email marketing discount offer Squarespace

9. Use product analytics to your advantage

It’s important to remember that the conversion rate isn’t the only metric a SaaS company should be looking at. See which features trial users interact with before coming customers, which stages of the user journey have the highest drop-off rate, or what the average session time is.

This is even easier for freemium products since you’ll have analytics from hundreds or thousands of free users that have been using your software for weeks, months, and even years — all of whom can provide insights that will help you optimize for your target market.

Whether it’s pivoting towards a new audience, improving the in-app experience, tuning specific features, or optimizing your marketing strategy, there’s no question that free trial users can offer plenty of invaluable data.

Specialized software like Userpilot will help you track user activity, monitor engagement metrics, and trigger specific messages or events based on specific user actions. The best part is that you can create these in just a few clicks without writing a single line of code.

No-code webhook Userpilot
Userpilot webhooks.

10. Approach users after the trial expires

Last but not least, your free trial marketing strategy shouldn’t end when the trial does. Whether or not trial users convert into paying customers, you should follow up with them to hear about their experience and what they would’ve liked to see during the trial period.

Requesting user feedback through in-app microsurveys or email surveys will help you identify opportunities that you’re missing out on. You could also offer trial extensions, permanent discounts, extra features, and other incentives to turn your best leads into customers.

Typeform has been known to offer discounts of up to 25% during win-back campaigns in an attempt to acquire new customers and boost their free trial conversion rate. Here’s an example of one of their win-back emails:

Typeform’s user win-back email.

To conclude

As you can see, fine-tuning your free trials to maximize conversions doesn’t have to be rocket science. If you build an effective free trial marketing strategy with the tips above, you’ll have website visitors signing up for your free trials in no time!

Ready to get started with in-app messaging, no-code webhooks, and other features that will optimize your free trials? Sign up for your free Userpilot demo today!

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