[2] He served as executive producer of Stealing Ur Feelings, Noah Levenson's interactive film about emotion recognition AI in consumer applications.

[3] He took part, alongside his fellow directors Daniel Cross and Mila Aung-Thwin (all three of the EyeSteelFilm production company) in a National Film Board of Canada initiative to teach Inuit students in a high school in Inukjuak, Nunavik (Quebec) to document their final year in the high school through film.

The result was Inuuvunga: I Am Inuk, I Am Alive a joint 58-minute 2004 documentary by 8 students from the Inukjuak - Innalik School.

As the title suggests, this documentary is particularly interested in the "legally grey area" of remixing existing works.

: A Remix Manifesto was shown at the International Documentary Film Festival Amsterdam (IDFA) in November 2008,[7] where it won the Audience Choice Award.

In 2009, Gaylor was named the winner of the Don Haig Award from the Hot Docs Canadian International Documentary Festival.