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Robert O'Callaghan has a diverse work experience spanning multiple industries. Robert started their career at Smyths Toys Superstores in 2009 as a Sales Assistant and Bike Mechanic, where they gained experience in various departments and received training as a bike mechanic. In 2016, they joined Apple as an At-Home Advisor, providing customer support remotely. Robert then interned as an Analyst at Dell EMC in 2018. From 2019 to 2022, they worked at FireEye, Inc. as an Associate Technical Support Engineer. In 2022, they joined Trellix as an L2 TSE and later transitioned to the role of Technical Support Engineer. Currently, they are working as a Cyber Threat Analyst at COFENSE.

Robert O Callaghan attended Munster Technological University from 2015 to 2019, where they pursued a field of study in Information Technology. During their time there, they did not obtain a degree. Additionally, they obtained certifications as a Support Professional from SGSA in July 2021 and as a Dell EMC Proven Professional Associate from Dell EMC in April 2018.