The Royal Literary Fund has supported professional writers for over two centuries — but its website told a different story. Stakeholder interviews surfaced consistent pain points: confusing navigation, information overload, visually outdated presentation, and copy that obscured rather than clarified the grant process. For an organization serving a predominantly older, technology-challenged audience, these weren't minor inconveniences — they were barriers. Discovery started with structured stakeholder surveys and listening sessions across RLF's departments, surfacing five distinct audience personas: grant applicants, potential associates, students, literature enthusiasts, and literary sector professionals. Each had different goals, different pain points, and different paths through the site. Alongside stakeholder synthesis, we conducted peer analysis across comparable organizations — Help Musicians, Arts Council England, the Ford Foundation, and others — to understand how peer institutions handled content hierarchy, grant communication, and accessibility. That research became the foundation for an information architecture that reduced cognitive load, clarified the grant pathway, and gave each audience a legible route through the site.