Ollie has responsibility for curriculum, pedagogy and innovation at Education Scotland. This responsibility includes major national initiatives, such as the ongoing implementation of Curriculum for Excellence; Glow; STEM; Developing the Young Workforce; Digital Learning and Teaching; the Learner Journey; 1+2 Languages; Inclusion, Wellbeing and Equality and Curriculum Innovation (including pedagogy and assessment).

Immediately before re-joining Education Scotland he was Global Director: Connecting Play and Education at the LEGO Foundation where he led the Foundations work related to education improvement through the use of technology and play. Prior to joining the LEGO Foundation he was headteacher of Kingussie High School, Highland. He started his career at the Glenmore Lodge (the sportscotland national outdoor training centre) before becoming a geography teacher and going on to hold a number of promoted posts in East Lothian.