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Leslye is a playwright, screenwriter, a film and television director and producer. In 2012, Headland wrote, directed and produced Bachelorette, starring Kristen Dunst, Lizzy Caplan, and Isla Fisher. She is the screenwriter for About Last Night, a romantic comedy based on Sexual Perversity in Chicago, a play by David Mamet. Her feature, Sleeping With Other People, which she wrote, directed and produced, stars Jason Sudekis and Alison Brie, and premiered at Sundance in 2015.

Russian Doll, on Netflix, was co-created, produced, and directed by Headland, earning her two Primetime Emmy Award nominations for Outstanding Comedy Series and Outstanding Writing for a Comedy Series. Leslye has directed episodes of Blunt Talk, SMILF, Heathers, Black Monday, Almost Family, and directed the pilot of Single Drunk Female.

In 2024, Headland was the writer, executive producer, and showrunner of The Acolyte, a Star Wars series and the second most-watched original series on Disney+.