Born in St. John's, Newfoundland. Moved to Montreal in 1910, when his widowed mother married well-known Canadian artist, Maurice Cullen. He found he was attracted to the artistic life. He helped his stepfather with chores in the studio and began sketching himself. He studied figure drawing at the Royal Canadian Academy and learned landscape painting with Cullen. He was recognized as a gifted student by instructor William Brymner at the Art Association of Montreal, who offered instruction to the penniless young artist free of charge, on the condition that he would pay the fees when he was able.

After serving overseas in WW1, he returned to Montreal and was invited to participate in the first Group of Seven exhibition in 1920. For a time, he concentrated on the etching medium, with the desire to develop his own style, apart from that of his stepfather. He was given the opportunity to study in Paris with the help of a generous patron and traveled to Paris in 1920. There he studied at the Académie Julian and exhibited in the Paris Salon in 1922. On his return to Canada he was elected an associate of the Royal Canadian Academy. Exhibiting with the RCA gave him more visibility and some of his works were acquired by the National Gallery of Canada.

After several successful exhibitions, he traveled abroad, painting in France, Spain and North Africa. In addition to oil paintings and etchings, he also worked in pastel, and completed several mural commissions in public buildings. More successful shows followed and he continued to paint, although he served his country once again in WW2. His Canadian impressionist painting style was shaped by his years in France, and the influence of his stepfather, Maurice Cullen, and the work of J. W. Morrice, whom he greatly admired. He was elected president of the Royal Canadian Academy in 1952.

Pilot died in 1967, and was honored with a retrospective exhibition at the Montreal Museum of Fine Arts in 1969.