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Sean Cunningham began their career in 2007 as a WiFi Technician at RFTechnologies. In this role, they ran verification testing for wi-fi-based real-time location system software for the PinPoint division, tracked software defects and created daily bug reports, and collaborated with quality assurance personnel. In 2009, they became a Latin Instructor and Editorial Assistant at Western Michigan University, where they taught introductory level Latin courses, developed coursework, assignments, and tests, and designed a multi-page website for students to exercise their understanding of grammatical concepts. In 2011, they joined RF Technologies again as a Software Developer, where they contributed substantially to the porting of their primary web client applications from Flex to GWT and Angular, and independently set up their development process. In 2016, they moved to DCI Marketing as a Senior Software Developer, Front End Solutions Architect, and Front-End Developer Contractor. In this role, they standardized the adoption of Angular for new front end projects, took point on integration of Angular into their . Net MSBuild publishing processes, and selected front-end technologies for multiple new customer-facing sites. Finally, in 2021, they joined Railroad19 as a Senior Front End Engineer.

Sean Cunningham completed a Bachelor of Arts in Latin and Medieval Studies and Linguistics from St. Olaf College in 2007. Following this, they attended the Medieval Institute at Western Michigan University, receiving a Master of Arts in Medieval Studies in 2011.