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Raymond Maldonado began their work experience in 1986 as a Service Technician at Record Systems Inc. Raymond held this position until 1998. In 1998, they joined Signtech as a Field Service Technician, responsible for the installation, service, and technical support of wide format printers. Raymond also provided customer training. Raymond worked at Signtech until 2001.

From 1999 to 2007, Maldonado worked at NUR Macroprinters, first as a Service Manager for Latin America, where they managed and directed the Latin America Service Department, planned installation of wide-format printers, and provided field service. Then, they became a Product Leader until 2007.

From 2007 to 2009, Maldonado worked as a Field Service Engineer at Gandinnovations.

From 2009 to 2014, they joined Polymeric Imaging as a Digital Sales and Technical Support, responsible for sales of digital inks and providing technical support for digital products and equipment.

Since 2014, Maldonado has been working at Roland DGA as a Service Account Manager, where they serve as the lead service adviser to the dealer channel in their territory, ensuring that service by dealers/service centers is conducted efficiently and up to the standards of Roland DGA Corp.

Raymond Maldonado earned their HS Diploma from Louis W. Fox Academic and Technical H.S. between the years 1981 and 1985. During their time at the high school, they focused on all academics, with a particular emphasis on Math and Computer Science. Following their high school education, Raymond pursued further studies at CBM from 1985 to 1987. At CBM, they obtained an AAS University degree in Electronics Engineers Technology.