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Oliver Fegan has held a variety of roles in the past. In 2003, they began their career as a Marketing Executive for Enterprise Ireland. Two years later, they moved to Accenture as a Management Consultant. In 2008, they took on the role of Business Development Director for Fegans Foodservice, where they managed the sales and marketing functions and developed new product ranges. In 2012, they founded Temptster, an app which revolutionized how people eat and drink, and became the number one selling app in the Irish iOS app store. Finally, in 2014, they co-founded usheru.

Oliver Fegan received their BA in Business & Economics from Trinity College Dublin in 2003, followed by an MSc in Responsibility & Business Practice from the University of Bath in 2007. In 2010, they earned a Diploma in Strategic Marketing for the Tourism Industry from Cornell University. Oliver also attended Castleknock College prior to their university studies.