Chesley is from Makkovik and worked in Nunatsiavut most of his life, spending 30 years working for a combination of the Labrador Inuit Association, the Labrador Inuit Development Corporation, Inuit Taparisat of Canada and the Nunatsiavut Government. Ches has experience as the senior deputy minister in the Nunatsiavut Government, land claims negotiator, IIBA negotiator, mineral resource advisor, self-government advisor, caribou plant manager and a former commercial pilot. Ches is currently working as a Vice President, Labrador Affairs with Aurora Energy Resources.
Chesley was appointed on September 20, 2016 by the Nunatsiavut Government.