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Robert Ushkevich has extensive work experience in the insurance industry. Robert began their career in 2001 as a Supervisor at OneBeacon Insurance, where they worked until 2005. From 2005 to 2015, they served as a Case Manager at RiverStone Claims Management and later at RiverStone Resources. In 2017, they worked as a Casualty Claims Adjuster at Utica National Insurance Group. In 2018, they joined Ahold Delhaize as a Claims Analyst, and in 2019, they became the Assistant Vice President - Complex Claims at National Claim Services LLC.

Robert Ushkevich attended the University of Connecticut from 1988 to 1992, although the degree and field of study they pursued during this time are unspecified.