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Jessica Cearfoss has worked in various roles since 1998. Jessica began their career as an Intern at Walt Disney World in 1998, followed by a GIS Technician role at Spatial Systems Associates, Inc. in 2001. In 2002, they worked as a GIS Technician with the City of Baltimore, Mayor's Office, Enterprise GIS. Jessica then worked as a Technical Writer at Thomas Associates, Inc. in 2003, followed by a GIS Specialist role at McCrone, Inc. in 2004. In 2007, they began working at RouteSmart Technologies, Inc. as a Technical Sales Engineer, followed by a Business Development Manager role at the same company in the same year. As Business Development Manager, they specialize in the public works sector and is the main point of contact for customers throughout their relationship with RouteSmart. Jessica helps prospects understand route optimization and how RouteSmart software can harness their data to achieve their performance goals.

Jessica Cearfoss attended Anne Arundel Community College from 1997-1998, where they obtained a Legal Studies degree. Jessica then attended the University of Maryland from 1999-2001, where they received a Geography degree with a focus on GIS and Italian.