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Cynthia Simms has a diverse work experience spanning over several years and industries. Cynthia started their career in 1990 as a Government Access Producer for the City of Evanston, where they managed all corporate video needs and was responsible for live event production and budget management. Cynthia then worked as a Palm Support Specialist for US Robotics and 3Com, providing technical support and training to customers. In 1999, they became the Technology Administrator for Anshe Emet Synagogue, where they oversaw all technology operations and designed a migration to a new network and system. Cynthia later joined the College of American Pathologists as a Support Specialist before moving to Hitachi Data Systems in 2008. At Hitachi, they served as a Sr. Client Services Engineer, responsible for IT support and services for the Americas region. In 2015, they joined Sears Holdings Corporation as a Unified Communications Analyst II, where they played a key role in the successful deployment of a new unified communications solution to over 9,000 users. Most recently, they worked as an IT Support Administrator for Sagent Pharmaceuticals.

Cynthia Simms attended Columbia College Chicago from 1990 to 1992, where they studied Corporate Video Production. However, it is not mentioned whether they obtained a degree during their time at the institution.