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Jessica Winter has a diverse work experience spanning multiple industries. Jessica began their career at Kohl's in 2004 as a Retail Associate and then moved to Walmart in 2005, where they continued to work as a Retail Associate until 2009. From 2009 to 2019, Jessica worked at Guardian Protection, where they held various customer service roles, including Customer Service Representative, Customer Service Team Lead, Customer Service Subject Matter Expert, Customer Service Trainer, and eventually Customer Service Supervisor. In 2019, they joined A3 Smart Home as a Team Lead and then progressed to become the Operations Lead. Jessica later served as the Technical Support Manager, where they successfully improved service levels and resolved team member concerns. Currently, Jessica holds the position of Director of Enterprise Transformation at A3 Smart Home, a role they assumed in May 2022.

Jessica Winter attended the Community College of Beaver County from 2005 to 2007, where they earned an Associate of Science degree with a focus on General Studies. In July 2020, they obtained a certification as an Alarm Company Employee from the State of California.