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Jimmy Benson has a diverse work experience that spans across various roles and industries. Jimmy started their career as a teacher in District 300 Schools and eventually moved on to teaching roles at Harry D Jacobs High School and James Island Charter High School. During their time at CHSD 155 School District, they taught engineering-related subjects and also served as the head tennis coach. In 2019, they became the owner of Benson Engineering and Construction LLC. Their most recent roles at Project Lead The Way include Director of School Success, Director of New District Engagement, and Director of New Product Sales, where they were responsible for developing strategic plans, engaging with clients, and driving growth for the company.

Jimmy Benson attended Northern Michigan University from 2004 to 2009, where they obtained a Bachelor's degree in Secondary Education and Teaching.