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Stephen Caffrey has a diverse work experience. In 2005, they started their career as an Associate at Bank of Ireland, where they worked until 2007. Stephen then moved on to BNY Mellon as an Associate, from 2008 to 2009. In 2010, Stephen joined Adotomi, first as a Project Manager from 2010 to 2011, and later as VP of Partner Development from 2011 to 2011. From 2012 to 2013, they worked as VP of Publishers at Woobi. In 2014, Stephen became the CEO of display.io. In 2022, they took on the role of Investor at Wizyu and founded Sponsorcart.io.

Stephen Caffrey completed a BA in Philosophy and Politics at University College Dublin from 2001 to 2004. Later, from 2004 to 2005, they pursued a HDip in Business and Entrepreneurial Studies at the same institution.