Phillips spent much of his career as a small business owner and commercial pilot. He is best known, however, for his time as a politician and head of state serving Yukon. He was first elected to the Legislative Assembly in 1985. He served in elected politics for 15 years, including several roles in the Cabinet of John Ostashek’s Yukon Party government. His cabinet posts included Minister of Tourism, Minister of Education and Minister responsible for the Women’s Directorate, Minister of Justice, and Minister responsible for the Public Service Commission.
In 2004 he joined the Yukon Land Use Planning Council, where he served several years as member and chair. Wildlife conservation is important to Phillips, and he has served his community in a variety of related capacities, including as part of the Task Force on Northern Conservation and the Yukon River Salmon Negotiating Team. In 2009, Phillips was adopted into the Carcross/Tagish First Nation’s Deisheetaan clan.
In December 2010, Prime Minister Stephen Harper announced the appointment of Phillips as Yukon commissioner, a post similar to lieutenant-governor in Canadian provinces. He succeeded Geraldine Van Bibber. Phillips served as commissioner until 2018, when Angélique Bernard replaced him.