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Donald Jacobs has a diverse work experience spanning over a decade. In 2012, they worked as a Sales Intern at Elite Remodeling, where they developed sales pitch scripts and built relationships with potential customers. From 2016 to 2017, they were a Construction Laborer at Walsh Construction Co., assisting in the construction of an apartment building and coordinating priorities with the superintendent. In 2017, they worked as a Construction Laborer at R&D Wireless, LLC. In 2018, they joined WatchTower Benefits as an Account Planner. Since 2009, they have been a Co-Owner at Don Jacobs Services Inc., where they manage a snow plowing and landscape company, operates heavy equipment, and oversees employees. Most recently, in 2020, they became a Freight Broker at Summit Logistics Group.

Donald Jacobs attended Columbia College Chicago from 2013 to 2018, where they obtained a Bachelor's degree in Marketing. In addition to their degree, they also obtained various certifications from the Chicagoland Laborers District Council Training Fund, including Burning, CPR/First Aid, Flagger, ICRA, MEA Computer, OSHA 30 hr, Pipeline Tech, Scaffold Tech, and Trench Safety.