 He coached NUI Maynooth to Collingwood Cup glory for the first time in their history in 2014 by defeating NUI Galway in the final.In 2014, O'Brien was appointed as Director of Football for the schoolboys section at St. Francis.The club won two All Ireland trophies in his time and 7 players were transferred to the UK.In November 2016, O'Brien progressed to being appointed as Director of Football for the underage teams at St Patrick's Athletic, he would also take up a coaching position with the first team while continuing to play.