Our research partnership with ioMoVo aimed to identify key pain points in their Digital Asset Management (DAM) platform using Jakob Nielsen's usability heuristics. Insights from this heuristic analysis informed our hypothesis on critical issues in the file retrieval journey, from connecting cloud storage platforms to efficiently locating specific files within petabytes of data via Al-powered natural language processing. We validated the hypothesis using mixed research methods and proposed solutions emphasizing simplicity, intuitiveness, a short learning curve, recognition over recall, and alignment with users' familiarity with the system.