Sherpa Insurance was a digital-first insurtech designed to offer simplified, personalized protection solutions via an automated pricing engine. Heuristic evaluation and early user testing identified critical onboarding bottlenecks: high-contrast purple background container fills distracted users, and extremely long forms created scrolling anxiety, resulting in high drop-off rates at the initial stages of the quoting funnel.

Users were overwhelmed by excessive binary YES/NO decision points that forced them to answer questions rather than select options dynamically. Additionally, real-time pricing calculation through the Certua API suffered from integration latency, leaving users staring at inactive screens during crucial progression steps.

To address these issues, we redesigned the onboarding flow into a conversational journey. We replaced YES/NO questions with visual selector tiles and grouped inputs into compact, floating cards positioned entirely above the fold to eliminate scrolling. We clean-structured the progress bar for better user orientation, integrated the warm FS Joey typeface, and designed custom animated transition states to reassure users during API calculations. Testing validated that these enhancements significantly reduced cognitive load and drop-offs.