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Paul Riley has a diverse work experience spanning over multiple companies and roles. Paul started their career in the US Army, serving as an Airborne Infantry, Operations NCO, Platoon Sergeant, and Gold Badge Recruiter from 2001 to 2007. Afterward, they founded their own company, RileyTek, Inc., where they served as the President and CEO for eight years. Following that, Paul worked as an Information Systems Analyst II at the State of Illinois from 2008 to 2013. Paul then transitioned into the private sector, working as a Senior Application Developer at LRS from 2013 to 2014. In 2015, Paul worked as a Consultant at MSF&W before joining Horace Mann as a Sr. Application Developer. Paul also worked as a Consultant (Senior Application Developer) and later as the Chief Technology Officer at the Illinois Department of Transportation from 2016 to 2019. Most recently, Paul joined Dot Foods in 2019 as a Lead Software Engineer.

Paul Riley has a diverse education history. From 2013 to 2016, they attended Western Governors University, where they pursued a Bachelor of Science (BS) in Computer Science with a specialization in Software Development. Prior to that, from 2009 to 2011, they studied at Robert Morris University - Illinois, focusing on a Bachelor of Science (BS) in Computer Science and a Master of Science (MS) in MIS (Management Information Systems). Additionally, in 1996-1997, they attended Northern Illinois University.

Alongside their education, Paul also holds several certifications. Paul obtained the Microsoft Certified Solution Developer (MCSD) certification from Microsoft in May 2018. Paul also achieved the Project Management Professional (PMP) certification from the Project Management Institute (PMI) in September 2010. More recently, in August 2021, they obtained the Microsoft Certified: Azure Solutions Architect Expert certification twice from Microsoft.