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Simon Pepper has a diverse work experience in the insurance industry. Simon began their career at Swiss Re as the Head of Underwriting and Claims. Simon then worked at Friends Provident as an International Marketing Manager. Simon joined Allianz Reinsurance as a Senior Risk Manager before moving to Pacific Life Re (Asia) as the Head of Underwriting and Claims. After that, they worked at Allianz Partners as a Regional Underwriting Manager for Group Life and Disability. Currently, they hold the position of Chief Underwriter at Transamerica Life Bermuda.

Simon Pepper obtained a Bachelor's degree in Biochemistry from the University of Liverpool.