As the lead designer, I worked cross-functionally to transform a non-usable POC into a functional AI Assistant embedded in our asset management platform. After observing that users were frustrated with irrelevant prompts and dead-end responses, I redesigned the assistant to display context-aware suggestions and integrate seamlessly into the side panel. I also introduced features like in-line reporting, system-aware insights, and safe human-in-the-loop email drafting. These improvements helped rebuild client trust and played a key role in securing a multi-year contract. Although not all features shipped, the new design significantly improved user satisfaction and usability.