At KH Creative, we believe design is about more than interfaces—it’s about shaping how people feel when they interact with technology. When Alley Cat AI Works set out to build Ally, their AI assistant, we joined forces to explore what it means to trust and use AI in everyday contexts. What began as a simple website chatbot quickly evolved into a larger vision: a voice-first, multi-modal assistant. By interviewing stakeholders, analyzing design patterns, and testing early prototypes, we uncovered the key elements users needed—clarity, trust, and flexibility. This case study walks through our design journey, from sticky-note walls to the pivot toward voice interaction, and highlights how thoughtful UX can turn an AI tool into a human-centered experience.