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Jason Medeiros began their work experience in 1995 at MEDITECH as a Conversion Consultant/Programmer. In 1997, they joined REI as a Retail Sales Specialist, where they worked intermittently. In 1999, Jason started working at Iatric Systems as a Support Programmer, responsible for installing and supporting software applications. Jason later served as a Product Manager, leading the installation and sales of Iatric Systems Security Audit Manager. Jason also worked as a Project Manager and Director of Technical Services at Iatric Systems, overseeing installations, maintenance, and designing processes. In 2017, they joined Protenus as a Senior Project Manager.

Jason Medeiros attended Westfield State University from 1991 to 1995, where they earned a Bachelor's degree in Psychology.