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Robert Boakai has had a long and varied career in the technology industry. Robert began their career in 1999 as the Vice President/Founder of JenXSystems Inc. Robert then moved on to Apptis Inc. in 2004, where they served as a Sr. Systems Engineer. In 2006, they took on the role of Director, Information Technology at Datatrac/CSC. In 2007, they became Vice President at Paradigm Solutions. In 2014, they moved on to DMI (Digital Management, Inc.) as the Vice President, Financial & Regulatory. In 2015, they were the Sr. Vice President, Public Sector at ECCO Select. Finally, they are currently the Vice President at Educology Solutions, a position they have held since 2016.

Robert Boakai received their B.S. in Computer Science from the University of Maryland Global Campus between 1990 and 1995. Robert then went on to The Johns Hopkins University, where they earned their M.S. in Systems Engineering between 2000 and 2003.