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Matthew Oldenburg has had a diverse work experience. Matthew started their career in 2010 as a Physical Education & Health Teacher at LUMIN Schools. In 2012, they transitioned to Cintas where they held multiple roles, including Health & Safety Specialist, Service Sales Representative, and Eye Wash Technician. Matthew then joined the Milwaukee School of Engineering as an Assistant Track & Field Coach in 2010, where they worked until 2012. In 2014, they joined Silver Lake Auto & Tire Centers as the Director of Operations, and later became the General Manager. Matthew also simultaneously served as the Shop Manager and Service Advisor at Silver Lake Auto Center from 2014 to 2022.

Matthew Oldenburg attended Concordia University-Wisconsin from 2007 to 2010, where they obtained a Bachelor of Education (BEd) degree in the field of Education. In addition to their formal education, they hold additional certifications including ASE Certified Service Advisor from the National Institute for Automotive Service Excellence (ASE) and OSHA 10 Certified from OSHA 10 Hour Training. The specific dates of obtaining these certifications are not provided.