In 2012, Bailey was named artistic director of the Toronto International Film Festival.

[4] He participated in the 2015 edition of Canada Reads, where he advocated for Kim Thúy's novel Ru.

[6] In 2018, Bailey was promoted to the newly created position of artistic director and co-head of the Toronto International Film Festival.

[7] In 2021, following the resignation of co-head Joana Vicente, Bailey was named the festival's executive director.

[8] On November 30, 2021 Bailey was appointed Chief Executive Officer of TIFF after a 25 year career with the festival.