At the age of 16, Gwaai Edenshaw was mentored by renowned Haida artist Bill Reid. At 18, he worked on his first totem pole project under his father Guujaaw. This 40-foot totem now stands in Indonesia. Since then, they have completed more than three poles together, and he has also worked on a few totem pole projects with his brother, Jaalen. In 2001, Gwaai assisted Michael Nicoll Yahgulanaas with his graphic novel A Tale of Two Shamans. This collaboration encouraged his interest in experimenting with Haida themes. Gwaai has since gone on to complete the Jewellery Art and Design program at the Vancouver Community College, where he learned about the process of casting. As well, he is one of the founding members of the Q'altsi'da Kaa players, who developed their first play to be performed entirely in the Haida language. Gwaai launched his unique line of jewellery, Regalia, in 2009, which features cropped bentwood box designs from the Raven creation story. In 2012, he added additional designs to his Regalia line, featuring Naxiin (Chilkat) imagery in this signature style. In 2010, Gwaai was involved in the Vancouver Playhouse Theatre's production of Bruce Ruddell's play, Beyond Eden. He participated in many aspects of the production, for which he received a Jesse nomination. In 2012, Gwaai participated in Lattimer Gallery’s Annual Charity Bentwood Box Event. He worked with Métis/Cree artist James Michels to make and donate a decorated cedar bentwood box that was sold via silent auction to raise funds for Vancouver’s Urban Native Youth Association. In the summer of 2013, Gwaai assisted his brother in carving and raising a 42-foot pole in Gwaii Haanas National Park. This was the first pole raised in the Gwaii Haanas region in over 130 years. In 2019, he was featured in the landmark publication Understanding Northwest Coast Indigenous Jewelry by author Alex Dawkins.