From onboarding to win-back campaigns — how to prevent churn and retain customers for the long haul
Creating the optimal free trial experience is like perfecting a recipe. It involves a careful balancing act of ingredients (your product’s features) to achieve the desired outcome: converting free trial users to paying customers. Offering too many or too few features can hinder your results. The key is striking the right balance.
Timing is also of the essence. Just as you need to take something out of the oven at the perfect moment, the length of your free trial should be carefully chosen. All of these decisions depend heavily on your audience, as far as their expectations, acuteness, and personal preferences.
Throughout the free trial journey — before, during, and after — there are many steps a business can take to ensure success. Whether your goal is encouraging people to start a trial, converting users to paid, or winning back users who failed to convert, each stage offers opportunities for improvement.
Here is a list of useful tips to maximize your free trial program.
Be transparent
A successful free trial program starts with a clear understanding of what’s being offered and for how long. For SaaS products in particular, will the user have access to all features? How long will the trial period be, and what happens when it ends?
For free trials that require users to provide credit card or other payment information, clarity is crucial. Be explicit about the terms, including whether the user’s account will be automatically charged for renewal at the end of the trial — a common practice among streaming platforms, which often use what’s known as an "opt-out" model. In this setup, users must actively cancel before the trial ends to avoid being charged.
Alternatively, an "opt-in" trial doesn’t require a credit card upfront, meaning users can explore the product without any payment commitment, and are only prompted to upgrade once the trial concludes.
Since free trials are a common tactic in product-led growth (PLG) — a strategy that emphasizes easy product access to drive adoption — it’s also important that the trial experience clearly demonstrates key value propositions.
At the same time, a company must set realistic expectations about what users can achieve during the trial period, to avoid misunderstandings over expected ROI while still incentivizing them to convert to paid.
Provide proof
Just because a free trial is free doesn’t mean customers will automatically opt in — it still requires persuasive effort. (There is still a time investment, of course.) One of the best ways to incentivize signups is by providing social proof, in the form of reviews, testimonials, case studies, and other examples of users who benefited from your product. Studies have shown that video testimonials specifically can have an ROI of up to 500%, with 88% of marketing teams seeing boosts to their conversion rates.
Eliminate friction
Throughout your free trial, it’s vital to remove friction from the experience. Starting with enrollment, that means reducing the amount of input fields or requiring less information overall — longer form fills can lead to drop-off rates over 50%. You can also streamline the process by enabling social logins through existing user accounts.
Another important decision at sign-up is whether or not to collect credit card information. Data has shown that while requiring card info can discourage sign-ups, the same trials are more likely to convert to paid. Conversion rates are typically higher (north of 60%) for opt-out free trials vs. opt-in (higher than 25%).
During the duration of the free trial, your PLG strategy must ensure that no matter which product features are available (e.g., premium features are blocked), the user experience is not diminished or complicated. In some instances, a demo of your product can accompany the free trial to train users on how to navigate and use the platform (common for B2B SaaS). Components like tool tips can also be inserted throughout the platform to create a user-friendly experience in real time.
Finally, providing a friction-free experience should not end with the free trial. For users that don’t convert, but are “won back” through remarketing efforts (more on that later), it’s beneficial to make the reengagement process as seamless as possible (e.g., one-click reactivation) to avoid another lengthy onboarding process.
Analyze performance
The data collected from free trial programs is worth its weight in gold. There is so much to glean from how users interact with your product during the trial period, whether they’re ultimately converted to paid or churned out. Track these metrics using a comprehensive dashboard that measures everything from sign-up rates to win-back rates.
The free trial period is also an opportunity to observe how users behave (e.g., which features they use and for how long) from the onset of onboarding through different timed intervals (e.g., first 7 days, 14 days, 1 month). Usage patterns and trends can help determine why users convert and why they churn, which can strengthen user segmentation for future free trials.
Insights can also inform changes to product onboarding — like introducing guided walkthroughs or adjusting tooltip configurations — to better support trial users in discovering core value.
Personalize the experience
Free trial user data is the core of personalization, allowing you to tailor onboarding and end-user experiences that maximize conversion rates and expansion opportunities (e.g., cross-sells, upsells). By studying trial behavior, you can create segments that distinguish your power users (highly active and engaged) from your inactive users. Doing this allows you to craft marketing messages and prompts that hit their targets, whether you’re upselling additional features or creating reengagement campaigns.
In-trial personalization can include prompts that offer discounts, additional free months, or other incentives to encourage conversion. However, these offers should be measured so they don’t devalue your product in the long run. As you monitor ongoing levels of user activity, you can personalize free trials in real time with targeted and triggered offers, allowing you to optimize resources and reduce wasted spend.
Offer support
While reducing friction and personalizing experiences can help improve free trial success rates, an extended level of support should also remain firmly in place. In fact, customer support engagement during a free trial can significantly boost conversion rates, as it helps users overcome obstacles and builds trust in the product.
It’s important to proactively offer support rather than waiting for users to reach out, through a strategic campaign of in-app or platform messages, emails, and other communications that target periods of inactivity, limited feature use, and other telltale signs of disengagement.
Support channels can extend to real-time services like live chat, whether AI-automated or with a human in the loop. As dependent as SaaS users have become on automated prompts and messaging services, 82% of US consumers still desire human interaction for addressing their questions and concerns.
Renewal communication
The tail end of the free trial is the most crucial stage, as far as motivating users to convert. A well-coordinated series of timely nudges, typically via an email drip campaign, can incentivize users with reasons to stay, whether it’s the potential they can still unlock, additional features they can add, a premium service available for a discounted price, or more bluntly, the tools and features they're about to lose.
It’s wise to keep your messaging persuasive yet warm, avoiding any tone that feels pushy while users are still enjoying their trial. Renewal communications are also ideal for introducing cross-sell and upsell opportunities, presenting additional value beyond what’s included in the free offering.
Win back churned users
Optimal free trial strategy does not end with the free trial. Every missed chance to convert is a new opportunity to re-engage the customer through a win-back campaign, in which similar in-trial marketing tactics are used to turn churned users into success stories.
A win-back campaign is strengthened by first-party data gathered from the free trial. Did the user struggle with a particular feature? Were there noticeable patterns in their usage? Exit surveys can further optimize win-back efforts by revealing the main reasons users fail to convert. A win-back campaign can also include an extended free trial (either during or post completion date) to give your user more time to reach their “aha moment” (i.e., the decision to convert).
Bottom line
The main goal of any free trial is to convert users to paid. However, the data you collect can shape the entire customer experience — from onboarding best practices (opt-in or opt-out?) to understanding user potential, feature preferences, and product UX.
At Cleverbridge, we optimize every stage of your free trial program to ensure users have the best experience, leading to the best business outcomes: converting paid customers at scale. The key is creating the perfect journey from beginning to end, which requires the right levels of engagement, personalization, and incentives to drive the conversions you demand.
Whether it’s gamification programs (motivating users through checkpoints and “small wins” during trial) or personalized, high-intent offers, we understand the importance of knowing your customer.
Want to know more about how Cleverbridge can help with your free trials? Reach out to: grow@cleverbridge.com with any questions.
