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Michael Vaccarello has held various positions in the insurance industry since 1997. Michael began their career at IDP as Vice President in 1997. In 2006, they joined Sapiens as Vice President and in 2016 was promoted to Executive Vice President, NA P&C Business Development. From 2009 to 2016, they held concurrent positions at Maximum Processing, Inc. (A Sapiens Company) as COO and Vice President, where they were responsible for Stingray, a modular browser-based, property and casualty solution. From 2009 to 2023, they were COO of 4Sight Business Intelligence, Inc. In 2023, they joined Charlee.ai as Chief Revenue Officer (CRO), where they are responsible for the company's predictive analytics solution.

Michael Vaccarello holds an MBA in Information Systems from City University of Seattle and a BA in Computer Sciences from Misericordia University.