SQUARE ONLINE FREE TRIALS
Helping users experience value early
Designing a free trial experience that helps users experience value early. This project introduced a new free trial experience built to feel embedded within the product, making paid features visible and accessible from the start.
Role & Scope
I led design and strategy for the end-to-end free trial experience, partnering closely with Product, Engineering, and Analytics.
Square offers a forever free plan, but upgrading to paid tiers depended on whether sellers actually experienced value early on. The product showed plan options, but it didn’t clearly communicate what sellers would gain or how those features fit into their day-to-day workflows.
Key considerations:
Alignment across systems and teams
Improving paid conversion
Upgrade and downgrade clarity
Keeping onboarding friction low
Trial transparency and communication
Previous plan comparison
Treat the trial as a system
The trial was designed as a continuous experience rather than a single upgrade moment. It considers how sellers enter, how value unfolds over time, and how plan changes are communicated from start to finish.
We identified the paid features most likely to demonstrate value and defined the key levers to test in our initial experiment.
Introduce the trial carefully and with intention
Since this was a new experience, we rolled it out as a scoped experiment. We started with a small set of high-value features, limited entry points, and a controlled audience to understand how sellers moved through the trial end to end. This let us learn quickly while protecting existing onboarding and paid conversion flows.
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Our success criteria
20-25% lift (~$35K)
No negative impact on Square Online signup
No negative impact on Premium conversion
Design decisions
The free trial was designed to feel clear, predictable and grounded in user benefit.
Lead with the benefit
Paid features were introduced through previews and real, in-product examples. Sellers could see what was available to their specific business, how it worked, and what it would help them accomplish — allowing them to experience value before upgrading.
Billing transparency
At every point in the trial, sellers could clearly see:
What they were paying at that moment
What their next charge would be
Where to manage their subscription
Upgrading or downgrading clearly outlined what would change with each plan, so sellers could understand the trade-offs and make a confident decision.
Clear trial communication
Sellers were informed when their trial would end and where they could manage their subscription. Communication was designed to be clear and informative, so sellers understood what to expect at each step.
End-to-End Experience
The trial experience was designed in collaboration with the Themes team and refined through several launches, ensuring sequencing, plan transitions, and messaging worked cohesively and consistently across global markets.
Entry points
The trial appears contextually within onboarding and upgrade flows, minimizing friction while clearly surfacing value. Content is designed to be scannable, focused, and easy to understand at a glance.
Checkout & Billing
Billing details are clear and scannable, showing today’s cost, the post-trial price, and where to manage the subscription — reducing friction and uncertainty at checkout.
During the trial
Sellers can always see their trial status, remaining time, and where to manage their subscription.
Later iterations clarified which features were included, so sellers better understood what was available as they explored paid functionality.
Trial completion
At trial end, plan transitions are clear and predictable. Sellers can see what changes when upgrading or downgrading, with no surprises.
They have a straightforward path to make updates, reinforcing a sense of control at the moment of decision.
Results
The free trial improved conversion at each key step of the funnel.
47% of sellers who began signup entered the trial
46% of trial starters converted to a paid plan
International trial-to-paid conversion reached 27% on the same experience
Nearly half of sellers who entered the flow went on to experience paid features before committing. Metrics were paired with seller feedback.
Learnings & Next Steps
Helping sellers experience value early builds confidence and trust. Future exploration would focus on personalizing trial paths while maintaining clarity and transparency at scale.