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Darryl Siry currently serves as the COO & CTO at Cover Whale, beginning in November 2023. Previously, Siry held the position of EVP, Global CTO at SiriusPoint, where the development of a modern technology and operating platform facilitated the successful integration of Sirius Group and Third Point Re. Siry's extensive experience includes roles such as Chief Technology & Operations Officer at ProSight Specialty Insurance, where leadership focused on IT, customer experience, and digital operations, and earlier positions that included founding NewsBasis, leading marketing at Tesla Motors, and serving as SVP and CMO at Firemans Fund Insurance Company. Educational credentials include a BA in Economics from Brown University and an ACE in Management, Innovation, and Technology from MIT Sloan School of Management.