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Robert Callahan has a diverse work experience spanning over several decades. Robert started their career as an Accountant/Auditor at Thomas Havey & Co., CPAs in 1988, where they worked until 1991. Robert then joined the National Governors Association as Assistant Controller from 1991 to 1995. After that, they worked as an Accounting Manager at the National Association of Home Builders from 1995 to 1998. In 1998, they became Vice President of Finance & Administration at The Free Congress Foundation, holding the position until 2001. From 1998 to 2002, they also served as a Board of Education Member at Prince George's County Public Schools. Currently, they hold the role of Vice President and Chief Financial Officer of Finance & Administration at The Fund for American Studies since 2001.

Robert Callahan attended the University of Maryland from 1983 to 1987. During this time, they pursued a Bachelor of Science degree in Accounting at the Robert H. Smith School of Business.