Born in St. John`s Newfoundland in 1898, Pilot was surrounded by great artistic influences during his childhood. In his early life, Pilot's mother married Canadian artist Maurice Cullen. Pilot subsequently moved with his family to Montreal and became very interested in pursuing a career in the arts. During high school, Pilot was distracted during his classes and longed for the end of the day when he could go home and help his stepfather in his studio. Like many young artists, Pilot was taken on by Cullen as an apprentice where he received his early training.
Aside from the training given to him by Cullen, Pilot studied art at the Council of Arts and Manufacturers. There, Pilot studied under Edmond Dyonnet and learned drawing by studying objects and the human form. As part of his training, Pilot accompanied Cullen on weekend sketching trips where he began to familiarize himself with landscape painting. One of Pilot`s teachers William Brymner encourage him to continue his art education and allowed him to enrol in classes at the Association of Art in Montreal, free of charge. Brymner knew that the young Pilot had very little money and suggested that he could pay the school back whenever he was able to spare the money. However, Pilot's studies were interrupted when he enlisted to serve in the Canadian army during World War I.
Following the war, Pilot continued to have success in Montreal and was offered a spot in a Group of Seven show in May 1920. Despite his success, Pilot felt his work was somewhat over-shadowed by his stepfather's reputation. This led Pilot to begin working with mediums that Cullen did not use, such as etching. Working with these mediums allowed Pilot to differentiate his art from Cullen's.
Although Pilot was inspired by many artists of Canadian landscape painting, he maintained his own individual style. This style is much softer than the work of the artists Pilot was influenced by. In his older age, Pilot was elected president of the Royal Canadian Academy where he held office until 1953. He died in 1967.