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Rob Bailey's work experience starts in 1985 when they worked as a Junior Programmer for Dealformatics Ltd, a subsidiary of National City Brokers. Rob then joined Insight Software Ltd in 1988, where they worked as a Senior Developer and later became a Project Manager. In 1998, they joined Software Resources Ltd as a Senior JDE Developer, working on various projects for customers. In 2007, they started their own consultancy company called Jolirosa Consulting Ltd, specializing in JDE Development, Analysis, and Troubleshooting. During this time, they worked with several companies, including Baxter Healthcare, Tedcastles Oil Products, Merck Sharpe and Dohme, GSK Ireland, and Forza Consulting Ltd. In 2020, they joined Hight.io as a Solutions Architect, applying their skills in AI Powered Enterprise Applications.

Rob Bailey attended the College of Commerce Rathmines from 1983 to 1985, where they obtained a certificate in Commercial Computer Programming with a focus on Information Technology. Additionally, they attended De La Salle Raheny, although no specific degree or field of study information is available for this institution.