In 2004, Waugh was hired by Mark Shuttleworth as an early employee of Canonical Ltd. and member of the Ubuntu project, where he worked in business development.

[1][2] At OSCON in 2005, Waugh won "Best Evangelist" in the Google-O'Reilly Open Source Awards for his evangelism of Ubuntu and GNOME.

[3][4] He announced his resignation from Canonical in July 2006 to focus more fully on his work in the GNOME project.

[6] Waugh Partners won the 2007 NSW State Pearcey Award for Young Achievers for their work promoting Free Software to the Australian ICT industry.

Day, that he had been struggling with depression since his late teens, and that it had been a contributing factor to the divorce, but that he felt he had overcome it.