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Ben Woodward started their work experience in 2004 as an International Claims Analyst at Chubb. In 2006, they moved to ACE Westchester Specialty Group as an Underwriter, working in Professional Liability until 2008. From 2009 to 2010, they worked as an Intern at Dell in Global Field Delivery. In 2010, they joined Global Indemnity Group and completed their Management Training Program. Ben then served as a Manager of Professional Liability until 2011. From 2011 to 2014, they worked at Admiral Insurance Group as an Underwriter and later became a Senior Underwriter, specializing in Professional Liability. Since July 2018, they have held the position of Vice President of Professional Liability at Admiral Insurance Group.

Ben Woodward obtained their MBA in Finance from the University of Tennessee, Knoxville in 2009. Prior to that, they completed their BA in Sociology from Rollins College in 2004. In addition to their degrees, Ben also holds the certifications of Associate in Surplus Lines Insurance (ASLI) from the American Institute For Chartered Property Casualty Underwriters and Registered Professional Liability Underwriter (RPLU) from the Professional Liability Underwriting Society. The specific dates of obtaining these certifications are not provided.