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Richard Bessette's work experience starts in 1998, where they worked as a CAD designer and performed product delivery services for Select Die Works. From 2000 to 2001, they worked as a Quality Control Inspector at Material Sciences Corporation. In 2002, they became a Telecommunicator at the Stickney Police Department. At Best Buy, from 2003 to 2008, they worked as a Geek Squad Agent, diagnosing and resolving computer hardware and software issues for customers. From 2004 to 2023, they were an Information Technology Specialist at the Village of Oak Lawn, responsible for the systems within the police department. In 2016, they became an Information Technology Specialist at the Stickney Police Department, where they served as the Domain and Network administrator and project manager. Currently, Bessette is working as a Public Safety Solutions Project Manager at the City of Naperville, overseeing the development and deployment of integrated solutions to modernize public safety applications.

Richard Bessette has a Bachelor of Science degree in Business Studies in Computer Information Technology from Southern New Hampshire University, which they completed in 2018. In addition, they hold a Certificate in Associate Database Administrator from Moraine Valley Community College. Richard pursued various technology training at Global Knowledge and studied General Science at Moraine Valley Community College, where they obtained an AAS degree. Richard also has several certifications, including Netmotion XE Mobility Administrator from Netmotion, obtained in March 2013, and Emergency Number Professional - ENP from the National Emergency Number Association - NENA, obtained in October 2012. Richard is also a Certified Ethical Hacker (CEH) and holds a Microsoft Certified Technology Specialist (MCTS) certification.