Discord became our direct line to Sidekick users, fueling a user-centered design sprint approach. We embarked on iterative design sprints, conducting in-depth user interviews and surveys to understand their pain points and aspirations. This qualitative data informed low-fidelity wireframes, rapidly iterated upon through A/B testing and user walkthroughs. These initial explorations then evolved into high-fidelity mockups, meticulously refined based on user feedback from usability testing. This continuous loop ensured the Sidekick overhaul not only addressed their needs precisely but also elevated the overall experience. The user-centric focus extended beyond the interface. User journey maps and information architecture exercises helped us design an intuitive and discoverable experience. We also conducted card sorting and tree testing to ensure optimal navigation and information hierarchy. This resulted in crystal-clear documentation and effortless discoverability, empowering streamers to find the tools they need instantly.