McCaffrey was born in 1968 in Northern Ireland, and is a graduate of Saint MacNissi's College, Garron Tower in County Antrim and Selwyn College, Cambridge (1986–90) where he read Law and History.
He has worked for the Victoria and Albert Museum as Director of Development from 2002 to 2005, as a consultant to the Royal National Institute for Deaf People from 2005 to 2006, and the National Museums of Scotland. He also established the University of Ulster's first Development Office in Belfast in 1993 and has worked for Guinness plc (now Diageo) as PR and as a director in Belfast of ABSA (now Arts and Business). His client list has included the Catholic Bishops' Conference of England and Wales, Edinburgh College of Art, the Vatican Museums (of which he is a UK trustee), The Rosslyn Chapel, Worth Abbey and the World Monuments Fund (GB) amongst others. The Irish Episcopal Conference retained McCaffrey as their fundraising advisor for the International Eucharistic Congress which took place in Dublin in 2012. In 2010, he was the principal fundraising advisor for the Papal visit to the United Kingdom in September 2010. £6.5 million was raised towards the cost of the Papal Visit in 7 months.
While working for Cambridge University, he played a major part in securing the UK's largest ever charitable gift, $230M given by the Gates Foundation to Cambridge University in 1999.[3] He claims to have been involved in the first visit to Northern Ireland by President Bill Clinton and subsequent visits by Hillary Rodham Clinton, and helped to organise the second Millennium Lecture in the White House by Professor Stephen Hawking, hosted by the Clintons.
In January 2014 he was appointed as Global Development Director of the Sydney-based George Institute for Global Health. In February 2015 he was appointed as fundraiser to the Pontifical Academy of Sciences in the Vatican.