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Dipesh Radia has worked in various roles within the actuarial and underwriting field. Dipesh began their career at Momentum in 2006, where they worked as a Business Analyst in Product Values until 2008 and then transitioned to the role of Actuarial Analyst until 2011. In 2011, they joined Alexander Forbes as a Senior Actuarial Analyst until 2012, before being promoted to Head of Actuarial, Underwriting until 2016. From 2016 to 2020, Dipesh served as the Executive Head: Actuarial and Underwriting at Alexander Forbes. In 2020, they moved to Momentum, where they currently hold the position of Chief Commercial Officer.

Dipesh Radia completed their high school education at Crawford College Pretoria. Following that, they pursued a BSc degree in Financial & Actuarial Mathematics at the University of Pretoria/Universiteit van Pretoria.