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Courtney O'Leary has a diverse work experience in the software industry. In 2014, they started working as a Consultant at WorkflowMax (A Xero Product), where they stayed until 2016. Following that, they joined Xero as a Graduate Developer and later became a Full Stack Developer, working there until 2019. In 2019, Courtney joined Re-Leased Property Software as a Software Developer but left in 2022. In the same year, they worked as a Software Developer at Provoke Solutions before joining Stormforge as a Lead Vocalist. Currently, Courtney is starting a new role as a Software professional at Re-Leased.

Courtney O'Leary's education history begins with their enrollment at The University of Auckland from 2008 to 2010. During this time, Courtney focused on studying Physics, Mathematics, and Computer Science without completing a specific degree. Later, Courtney attended Enspiral Dev Academy until 2015, where they specialized in Software Development.