Flannery is a co-founder and the former CEO of Kiva.org and the current CEO of Branch International. He was the CEO of Kiva.org from 2005–2015. Flannery began co-developing Kiva in late 2004 while working as a computer programmer at TiVo, Inc. In December 2005 he left TiVo to work on the Kiva project full-time, with now ex-wife Jessica Jackley. Flannery graduated with a BS in Symbolic Systems, and a Master of Philosophy from Stanford University.