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Bob DiCosola has an extensive work experience spanning over several years. Bob started their career at the Federal Reserve Bank of Chicago in 1987, where they worked as a Staffing Manager until 1990. Bob then joined Dean Witter Discover as a Director of Staffing, working from 1996 to 1998. After that, they joined Jackson National Life as a Director of Staffing and Employee Relations from 1997 to 1999. Following this, Bob joined Old Second National Bank in 1999 as the Executive Vice President of Human Resources, Training & Development, and Diversity. Bob held this senior management position for over two decades, overseeing talent acquisition and management, workforce planning, succession planning, compensation/incentive plan best practices, organizational design, and leadership development. In 2013, Bob also took on a role as an Adjunct Faculty at North Central College, teaching HR Management at the School of Business.

Bob DiCosola attended Loyola University Chicago from 1987 to 1989, where they obtained a Master's degree in HR/Industrial Relations. Prior to that, they attended North Central College and Northeastern Illinois University, but no specific information is available regarding the dates or degrees obtained from these institutions. At Northeastern Illinois University, Bob pursued a Bachelor's degree in Journalism.