Since this effort was a rebuild of an existing application, our discovery work focused on validating known pain points and ensuring the redesign addressed both technical and user needs. We drew on years of prior user feedback and research to guide improvements, while collaborating with product and engineering through event storms, Boris diagrams, and service maps to confirm that backend changes would enable integration without disrupting critical front-end functionality. It was essential that the new application retained existing capabilities while resolving issues caused by outdated code and technical debt. From a design perspective, we concentrated on incremental but meaningful improvements—expanding the planning view window, introducing filters, and eliminating redundant data entry forms that were no longer necessary with suite integration. We looked to timeline-based delivery applications for inspiration and explored different workflow options through process and service mapping to simplify user interactions. Multiple mockups and prototypes were created, then iteratively tested with users through A/B testing, allowing us to evaluate the value of different views and filters, refine the workflow, and ultimately identify a UI approach that met planners’ needs.