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Bob Tomaszewski's work experience includes a variety of roles in the automotive industry. Bob started their career in 1991 at Genuine Parts Company as an Outside Sales and Store Manager. Bob then worked at Midway Truck Parts Inc. as a Store Manager and later as a Product Manager and Purchasing Manager. At Axle & Equipment Sales Co./Mack Truck service dealer, Bob served as the General Manager, managing day-to-day operations and improving profitability. Bob also worked at CIT Kenworth Chicago, where they were responsible for sales, management, and building the customer base.

Bob's experience also includes working as a Highway Fleet Manager & Fuel Buyer at Ryan Inc. Central, where they managed fleet purchasing, maintenance, and fuel supply. Bob later joined Navistar Inc as a Sr. Lead Project Manager, ensuring serviceability features were incorporated into product designs. Before their current role, Bob worked as a Territory Sales Manager at PetroLiance, LLC.

Since 2016, Bob has been employed at Wastebuilt Environmental Solutions, initially as a Field Service Representative and currently as a Midwest Parts Sales professional.

Bob Tomaszewski began their education journey in 1986 at Richard J Daley College, where they studied Marketing, Management, and Statistical Analysis. Bob attended this college until 1989. In 1989, they continued their education at Moraine Valley Community College, focusing on Industrial Electronics Technology/Technician. Bob completed their studies in this field and received a Certificate in LV Circuitry in 1990.