After several years working at a top talent agency, a studio, and several productions companies, Kaila York launched her own production company, Headlong Entertainment to further the stories she was passionate about telling. There she built a team of talented filmmakers and established a reputation for producing high-quality content across a range of genres. She has produced over 15 films, some of which she co-wrote, has filmed on locations around the world, and found distribution for all of her projects at television networks, streamers, and/or at major international film festivals. 

In the last six years, Kaila has directed eleven feature films, both thrillers and romantic comedies, that have premiered on networks such as Lifetime, UpTV, and Netflix. She has directed comedy legends such as Cheri Oteri and icons like Vivica A. Fox.

In addition to her work in film, Kaila is committed to promoting the industry by leading panels on independent film making, film financing, successful pitching, and other topics at various film festivals. She has been invited to speak at the Savannah Film Festival, Willamette Writers Conference, Hedgebrook Masterclass, and Fairhope Film Festival. As a member of the advisory board of the SCAD TVfest, hosted by the Savannah College of Art and Design (SCAD), she mentors young filmmakers and provides guidance to emerging talent.