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Deanna Reiss has a diverse work experience spanning several years. Deanna started their career in 2015 at Liberty Mutual Insurance, where they held various roles. Deanna began as an Associate I in the Analyst Development Program, performing analysis and contributing to short-term projects. Deanna then advanced to the role of Associate II, gaining skills in stakeholder management, project management, and data analysis. As a Senior Associate, Deanna acted as the Product Representative for Condo and Renters products, providing recommendations for future strategies and serving as the subject matter expert. Deanna also completed rotations in different departments, including the Solaria Labs Innovation Rotation, where they analyzed customer segmentation data, managed an internal newsletter, and contributed to a digital quote and bind initiative. Deanna eventually became a Senior Analyst, specializing in project management for Liberty Mutual's Internal Agency, leading strategic roadmaps and coordinating with Helmsman Insurance Agency. Additionally, they served as a Project Manager, building carrier relationships, developing reporting on strategic initiatives, and analyzing results for areas of improvement. In 2023, Deanna joined Openly as the National Agency Success Manager.

Deanna Reiss completed their undergraduate education at the University of Massachusetts Amherst from 2010 to 2014. Deanna obtained a Bachelor of Science (B.S.) degree in Hospitality and Tourism Management, as well as a Bachelor of Business Administration (B.B.A.) degree in Operations and Information Management. Additionally, in June 2018, Deanna obtained the Chartered Property Casualty Underwriter (CPCU) certification from The Institutes.