Headland, raised in suburban Maryland, graduated in 1999 from Staples High School. She received her BFA in drama from the Tisch School of the Arts at New York University in 2002.
Upon graduating college, Headland spent six years working as an assistant at Miramax, a year of which was spent as Harvey Weinstein's personal assistant. Her experience during that time is what inspired her 2012 play Assistance. As a playwright, she is best known for her Seven Deadly Sins cycle: Cinephillia (lust), Bachelorette (gluttony), Assistance (greed), Surfer Girl (sloth), Reverb (wrath), The Accidental Blonde (envy), and Cult of Love (pride). Part of the inspiration for the Seven Deadly Plays came from her Christian upbringing. Her final play in the series, Cult of Love, opened in 2018. She has also written a neo-noir style play The Layover which received mixed reviews in 2016.
Headland got her first job in the television industry in 2010 as a staff writer on the FX series Terriers. She wrote and directed the 2012 film version of her play Bachelorette, which was her debut as a feature film director. The film premiered at the Sundance Film Festival. Bachelorette co-starred Kirsten Dunst, Lizzy Caplan, and Isla Fisher as three troubled women who reunite for the wedding of a friend played by Rebel Wilson, who was ridiculed in high school.

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