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Ryan Cunningham has a diverse work experience. Ryan currently holds the position of CFO at Progress Rail, A Caterpillar Company since November 2023. Prior to this role, they served as the Controller and Business Manager for Rolling Stock at the same company from September 2020 to November 2023.

Before joining Progress Rail, Ryan worked at Caterpillar Inc. for many years, starting in May 2006. Ryan held various roles during their tenure, including Business Support Manager, Business Resource Manager for Large Mining Trucks, Business Manager for Technology Enabled Solutions and Go To Market, Business Resource Manager - Accountable Reporting, Senior Accounting Supervisor II, Senior Staff Accountant I, Staff Accountant II, Staff Accountant II - Accountable Reporting, Staff Accountant I - Accountable Reporting, Staff Accountant I - Sales Cost of Sales, and Accountant - Sales Cost of Sales.

Prior to their time at Caterpillar Inc., Ryan had internships at State Farm and LR Nelson in 2005 and 2004, respectively.

Ryan Cunningham earned a Bachelor of Science (B.S.) degree in Accounting from Illinois State University, completing their education from 2002 to 2006. In 2008, they obtained the Certified Management Accountant certification from the Institute of Management Accountants.