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Robert O'Brien has a strong background in the technology industry, with various roles in service management and technical support. Robert began their career at Network Equipment Technologies as an East Coast Unix Network Management Specialist, where they were responsible for managing the NET Network Management product for enterprise and government customers. From there, they moved on to USRobotics/3Com/UTStarcom, where they held multiple positions including International Service Director, National Service Director, and NYC Service Manager. In these roles, they managed a field service group and oversaw installations, consulting, and project management. O'Brien then joined Clever Devices as a Service Director, where they managed the installation, training, and maintenance services for the company's equipment on buses throughout North America. Currently, they work as the Executive Director of Technical Services and Training at John Mezzalingua Associates LLC, where they manage remote technical support, field support, and training delivery for multiple product lines.

Robert O'Brien attended Pace University from 1980 to 1984, where they earned a Bachelor of Business Administration (BBA) degree. Their field of study at the university was Business Administration and Management, General.