Optimizing the free trial journey to decrease chargebacks and refunds by 17%, and drive a statistically significant 23% increase in subscription upgrades.

The User Problem
Users enjoy Grammarly's free version and are curious about the premium features, but they often struggle to see the value in upgrading. Occasional premium suggestions are gifted and pique user interest, but these glimpses alone aren't compelling enough to convince them that the full suite of features is worth the cost.
Business Problem: The company wants to provide users with an opportunity to experience the full capabilities of its premium offering, aiming to drive upgrades and increase engagement. However, it must do so without negatively impacting revenue, ensuring that the experience encourages conversions rather than reducing paid subscriptions or increasing churn.
The Design Journey
Hypothesis: We believe that offering users a limited-time free trial will showcase the value of Premium, leading to an increase in subscription upgrades.
We initially targeted users through email with a limited scope. This approach successfully increased upgrade rates by 9% (post-refunds). Once we saw positive results, we expanded our efforts to include in-product messaging to further encourage enrollment and upgrades. As users navigated the flow, our aim was to build confidence in their experience and choices. To establish trust, we highlighted important details: users wouldn’t be charged today, they would receive a reminder email two days before the trial ended, and they could cancel anytime.
In-product messaging.
Free trial checkout screen.
This approach significantly increased enrollment, but we identified two concerns. First, higher enrollment didn’t necessarily lead to higher conversion rates. Second, we observed a rise in chargeback rates with Visa. Addressing these issues was critical to ensuring we met both user and business needs.
Free trial user journey.
Through user interviews, data analysis, and journey mapping, we uncovered three key opportunities:
Qualitative insights showed that although the free trial experience created a perception of added value, users couldn’t clearly articulate how, which decreased their confidence to upgrade.
Quantitative data showed that power users — who made up 30% of trial enrollments — converted at a disproportionately higher rate than other users, making them a prime audience to target.
Finally, our review of the cancellation flow revealed a confusing user experience that needed to be streamlined.
Streamlined cancellation flow.
Cancellation confirmation.
The Business Impact
By optimizing the key opportunities within the journey, we successfully decreased chargebacks and refunds by 17%, and drove a statistically significant 23% increase in subscription upgrades (post-refunds).
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