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Stephen O'Brien has worked in the IT industry since 2012. In 2012, they worked as a Lab Assistant at the University of Rhode Island. In 2013, they worked as an IT Help Center Consultant at the University of Massachusetts Amherst, Office of Information Technologies. In 2014, they were promoted to Lead IT Help Center Consultant at the University of Massachusetts IT User Services. In 2015, they took on the role of Network Administrator at Bloo Solutions Inc., where they provided frontline managed service IT support, network administration, Windows server administration, and monitoring of client machines. In 2019, they began working at Paragus IT, where they served as Client Support Manager and Client Support Engineer. In 2021, Stephen O'Brien joined Atlas Technica, where they currently work as Team Lead and System Engineer.

Stephen O'Brien attended East Longmeadow High School from 2007 to 2011 and then pursued a Bachelor's Degree in Biology, General and a Minor in Information Technology from the University of Massachusetts Amherst from 2011 to 2015. Stephen also obtained a Microsoft Certified Professional certification from Microsoft in April 2016 and a Network+ certification from CompTIA in June 2018.