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James Rawlings began their career in 1976 as a Software Developer for Computer Science Corporation, where they designed and implemented functions for the US Navy's Orion airborne platform and created a report generation language allowing end users to customize the system. In 1977, they joined Racal-Milgo as a Software Developer III, where they implemented a centralized network control center for modem, multiplexes and other equipment, as well as designed and implemented a disk management and cache system. In 1983, they became a Lead Software Developer for Equinox Systems, where they were responsible for the User Interface on matrix data switching systems. In 1993, they joined Sage and Greenway Healthcare as a Senior Product Analyst, where they worked closely with client facing support staff and clients to resolve software issues, triaged client issues to assess severity and organized product backlogs, and provided assistance to development staff to address software defects and enhancements. In 2016, they joined OPIE Software as a Software Support Manager and Technical Support, where they managed a staff of 12 Technical Support Agents, created and updated department policies and procedures to streamline the support process, and applied principles of Knowledge Centered Support and agility.

James Rawlings obtained a Bachelor of Science in Computer Science from the University of Maryland between 1974 and 1976. James also holds a certification as a Scrum Product Owner from the ScrumAlliance.