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Within the academic literature, limited attention has been paid to the issue of school leadership from an international and comparative perspective (Dimmock & Walker 2000). This paper contributes to the limited literature that does exist by considering how a project involving Canadian and Haitian school principals supported the leadership capacity of the leaders involved. Using digital technologies such as smartphones and tablet computers, participants engaged in an online professional learning community over a two-year period. This paper reports on three key themes that emerged from a qualitative research framework: collaboration and problem-solving, adapted leadership practices, and local and cross-cultural learning. These themes are examined in consideration of literature contending that localised leadership experiences inform cross-cultural learning (Moorosi & Bush 2011) and that school leadership requires a new conceptualisation of ‘glocalisation’(Brooks & Normore 2010). In the conclusion, suggestions for further research involving international collaboration in educational leadership are discussed.