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Cyndi Featherston has an extensive work experience in risk management and claims. Cyndi started working for R&B Falcon Drilling Co. in 1993 as a Claims Administrator and Supervisor, where they handled both domestic and foreign claims and coordinated with various stakeholders. Cyndi then worked for GlobalSantaFe Company as the Director of Claims, overseeing department policies and staff training. In 2008, they joined Hercules Offshore as a Risk Manager, where they developed and implemented a comprehensive risk management program and provided leadership to the Risk and Claims staff. In 2017, they worked for Lockton Companies as a Senior Claims Consultant, maintaining customer relationships and providing coverage analysis. Most recently, they joined TNT Crane & Rigging, Inc. as the Director of Risk Management, responsible for developing and administering the company's risk program and coordinating with insurers.

Cyndi Featherston obtained their Associate in Claims Designation degree from the Insurance Institute of America in 2000, specializing in Claims & Insurance. In addition, they hold various certifications, including the Associate in Claims from the IIA/AICPCU, obtained in 2001. Furthermore, they possess a Texas All Lines Adjuster License obtained in 1991 and a Louisiana All Lines Adjuster certification from the Louisiana Department of Insurance. The specific obtained month for the certifications is not provided.