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Rona Finkelstein has had two significant work experiences. Rona started in 2004 at IWIF as the Sr. Vice President of HR and Legal Services until 2009. Rona then joined Chesapeake Employers' Insurance Company in 2009 as the Sr. Vice President of Legal Services and Chief Compliance Officer, eventually becoming the Chief Compliance Officer in 2012.

Rona Finkelstein obtained a Juris Doctor degree in Law from the University of Baltimore School of Law.