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Bob Gladon started their work experience in 1998 as an ICT Consultant at LogicaCMG. Bob worked in this role until 2007. In 2002, they also started working as a Software Developer/Software Architect at Sanoma Uitgevers, a position they held until 2007. In 2007, Bob joined The Future Group as a Sofware Architect / Sr. Software Developer (Microsoft), and they are currently still in this role. Bob also briefly worked at Ormer ICT Dienstverlening in 2007 as a Solution Developer / Software Architect.

Bob Gladon attended Inholland University of Applied Sciences from 1994 to 1998, where they earned a bachelor's degree in Engineering with a focus on Werktuigbouwkunde (Mechanical Engineering). Following this, from 1998 to 2000, they enrolled in the Leiden Institute of Advanced Computer Science (LIACS) at CMG University Class, studying Information Technology. The degree earned at LIACS is not specified.