Uplisting's unified calendar presented confusing navigation and the absence of basic availability features, generating churn and loss of competitiveness. The proposed solution was a usability-focused redesign — monthly view, horizontal scrolling, and expanded search — with the goal of modernizing the experience and reducing operational friction.

Analysis of user feedback (Canny, with 250 votes for monthly view) and competitive benchmarks such as Guesty guided the scope decisions. The partnership between PM, design, and engineering defined two paths: migrate the current solution or redesign a new "My Properties" page. The flow was designed prioritizing contextual actions when clicking on dates — create reservation, block, adjust rates.

Development followed an MVP approach with a phased rollout to 20% of users. Implemented features included: monthly view, pagination removal, horizontal scrolling, and search by phone and email. These differentiators bring the platform closer to more modern competing solutions.

The expected business impact includes a 20% increase in self-serve conversion (from 5% to 6%) and a 10% reduction in weekly revenue churn. Design acts directly on retention by eliminating the main usability complaints that were motivating migration to other platforms.