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Michael O'Leary has extensive experience in software engineering and development. Michael began their career in 1994 as a Director of Engineering at MicroMass, where they led the development of rule-based personalization software. Michael then worked at koz and Ichat as a Senior Software Engineer, developing real-time messaging products using C++ and Java. In 2001, they joined Livewire Logic as a Senior Software Engineer, focusing on designing and developing their RealDialog software, an AI-based enterprise software for customer service applications. In 2006, they became a Senior Software Engineer at RealDialog, a division of Astute Solutions. Most recently, they have served as the Director of Software Solutions at Securboration since November 2015. Overall, O'Leary has a strong background in software engineering and has worked in various roles, from technical specialist to director, throughout their career.

Michael O'Leary pursued their education in the field of Computer Science. Michael completed their Bachelor of Science (BS) degree from Rensselaer Polytechnic Institute between the years 1986 and 1990. Following that, they furthered their studies by obtaining a Master of Science (MS) degree in Computer Science from North Carolina State University from 1994 to 1997.