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Josh O'Sullivan has had a long and varied career in the technology field. Josh began their professional journey in 2000 as a Programmer for ServiceChannel. In the same year, they also worked as a Systems & Database Designer for ProductivityNet. In 2001, they joined the US Navy as a Navy Information Professional and Surface Warfare Officer. Josh then moved to MITRE in 2009, where they served as a Cyber Operations Systems Engineer & Program Leader. In 2016, they became a Co-Founder of Protinuum and also began working for Ardalyst as their Chief Technology Officer and Principal. In 2018, they joined Celedon Partners (now Ardalyst) as their Chief Technology Officer and President, Federal Services.

Josh O'Sullivan has a varied educational background. In 2017-2018, they obtained an Executive Master of Business Administration from the University of Maryland - Robert H. Smith School of Business. Between 2004-2006, they earned an MS in Systems Engineering - Information Warfare from the Naval Postgraduate School. From 1997-2001, they obtained a BS in Computer Science and Psychology from Rensselaer Polytechnic Institute. O'Sullivan also has several certifications, including a Systems Engineering Works Program from the MITRE Institute (obtained in 2010), a CISSP from the International Information System Security Certification Consortium (obtained in 2008), a Joint Professional Military Education - Phase 1 from the Naval War College (obtained in 2006), and a Surface Warfare Officer (obtained in 2003).