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Matthew Grady's work experience begins in 1998 at Northwestern Mutual Life, where they worked as a Licensed Insurance Agent, establishing new customer accounts for health and life insurance. Matthew then moved on to Gallagher Bassett Services, Inc in 2004 as a Senior Claims Representative. From 2000 to 2005, Matthew worked at Liberty Mutual Insurance as a Senior Claims Representative, managing, investigating, and resolving high exposure claims. In 2005, they joined Pinnacol as a Senior Claims Representative III, where they managed, investigated, and resolved high exposure claims, including serving as a liaison for Other States Coverage. Matthew later became a Claims Specialist and then a Strategic Claims Representative, providing mentorship and training to other claims representatives. Matthew then joined CCMSI in 2014 as a WC Claims Supervisor before returning to Pinnacol Assurance in 2016 as a Claims Lead. Most recently, Matthew holds the position of Business Director at Pinnacol Assurance, where they are responsible for team financial and business performance measures and outcomes, as well as promoting strong working relationships with stakeholders.

Matthew Grady obtained an Associate degree in CPCU/ARM/AIC from the Insurance Institute of America from 2007 to 2012. Prior to that, they attended Illinois State University from 1997 to 2000, where they earned a Bachelor of Science degree in Business Administration and an Associate degree in Risk Management as part of their continuing education.