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Dan Keenan has a diverse work experience spanning different industries and roles. Dan began their career in 1997 as a Captain in the U.S. Army Finance Corp, serving until 2001. From 2001 to 2005, they worked as a Six Sigma Black Belt at General Electric (GE). In 2006, they joined National Interstate Insurance Company as a Business Development Manager, a role they held until 2010. From 2011 to 2015, they served as the Director of Business Development at Vanliner Insurance Company. Dan Keenan returned to National Interstate Insurance Company in 2016, first as Assistant Vice President of Specialty Transportation before assuming the role of Vice President of National Accounts in May 2021.

Dan Keenan attended Syracuse University from 1993 to 1997, where they obtained a Bachelor's of Finance and Economics with a specialization in Business, Management, Marketing, and Related Support Services. In 2015, they enrolled at Baldwin Wallace University to pursue a Master of Business Administration (M.B.A.), but there is no specified end year for this program.