Miles was a core employee at Rooster Teeth, working on editing and graphic design, as well as being one of the lead writers and directors of Red vs. Blue Seasons 10 through 13. He was promoted to Head Writer of Animation in 2015. In 2018 he stepped down from his position as Head Writer of Animation. He left the company in March 2020 to pursue personal interests while remaing active in RWBY's production.
He also makes regular appearances on the Rooster Teeth Podcast and has acted in numerous Rooster Teeth Shorts and other live-action productions, such as Ten Little Roosters.
In September 2020 he announced he is leaving Rooster Teeth, but will still continue writing RWBY and voicing Jaune Arc.