Problem

Users who wanted to explore premium features were hitting the same generic upsell modal—slow to load, stacked on top of other paywalls, and lacking context about the feature they clicked. This caused confusion, stalled exploration, and led to low upgrade conversion rates.

Approach

I redesigned the upsell experience to be contextual and value-first. Each feature received it's own dedicated upsell page with clear explanations, use cases, pricing options, and a subtle All Access offer. The double-paywall interaction was removed and we validated the changes through an A/B experiment measuring upgrade conversion and engagement.

Result

The new design delivered a 187% increase in upgrade conversion rate (0.9% → 2.6%) and a 143% increase in total upgrades. Users spent more time engaging with the content, better understood feature value, and experienced a smoother, more supportive upsell flow. This framework now powers scalable, contextual upsells across the entire Tithely platform.