In the digital age, technology is playing an important role in changing the nature of professionalism. Newer forms of professional learning stand in contrast to more traditional forms of professional development. The shifting paradigm has implications for school leaders in all contexts. This study sought to qualitatively examine how a sample of eight school leaders worked to support professional learning in their school communities and leverage tools in areas such as content aggregation, media creation, blogging and social media. In one-on-one and focus group interviews, participants discussed how technology is changing professional learning in their context and reflected on how their leadership has evolved in response to perceived challenges. Findings suggest that school leaders are aware of the importance of supporting professional learning through multiple device platforms, online networks and opportunities to play, and experiment with technology. Current issues identified include the need to shift from “buyer” to “driver” mindsets and to respond to the increasing role of popular thinkers whose ideas are amplified through online channels, such as social media.