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Jon Penwitt has a diverse work experience spanning several roles and industries. Starting in 1990, they worked as a Journeyman Electrician at Lamarche Electric Co for 16 years. In 2009, they became a Critical Environment Technician LII at Lee Technologies until 2011. From 2018 to 2019, Jon worked at Titan Electric as a Foreman/Electrician and then as an Electrical Foreman/Electrician. Jon then embarked on their own business journey as the Business Owner of Bristol Hill Homes, JP Construction, where they managed electrical contracting services and general contracting projects for residential and commercial properties. In 2011, they joined ComEd as an Electric Operations Supervisor until 2021, after which they became a Construction Manager until 2022. Currently, Jon works as a Project Manager at Seagate Development Group, starting in 2022.

Jon Penwitt completed an Advanced Certification in Overhead Lineworker at City Colleges of Chicago-Kennedy-King College in 2011. From 1990 to 1994, they attended Moraine Valley Community College, although no specific degree was mentioned for this period. In addition to their education, Jon Penwitt has obtained several certifications from Procore Technologies, including Procore Certified: Project Manager in Core Tools, Financial Management, Project Management, and Quality & Safety. These certifications were obtained in April 2022.