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Rob Hilliard began their work experience in 1978 as a Financial Analyst/Examiner at the Federal Reserve Bank of Chicago. In 1984, they joined LCP as the CFO. In 1999, they became the Director and Treasurer at Health Reach Clinic, where they worked until 2008.

Rob Hilliard completed their Bachelor of Applied Science (BASc) degree in Finance, General at Drake University from 1973 to 1977. Rob then pursued further education and obtained their Master of Business Administration (MBA) with a focus on Finance, General from Northwestern University - Kellogg School of Management between 1982 and 1986.