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Dennis Ryan's work experience begins in 2004 at ADP, where they worked as a Senior Client Services Representative. Dennis then progressed to the role of Technical Support Specialist in 2008 and later became a Technical Support Specialist III in 2011. From 2015 to 2017, they served as a Regional Project Coordinator at ADP, followed by the role of Program Specialist User Champion from 2017 to 2019. In 2019, Dennis joined Activu as a Technical Support Engineer, and eventually became the Team Lead for the Technical Support Engineer team in 2021. In the same year, they transitioned to Manages Projects/Technical Support as a Technical Support Specialist before their employment with the company ended in September 2019.

Dennis Ryan attended the Chubb Institute from 2003 to 2004, where they studied System, Networking, and LAN/WAN Management/Manager. Additionally, they obtained several certifications, including CompTIA Security+, CompTIA A+, CompTIA Network+, MCDST: Windows XP, and MCPS: Microsoft Certified Professional, from institutions such as CompTIA and Microsoft. Dennis obtained these certifications between 2009 and 2010.