When she was nine years old, she began taking voice lessons and joined a children's theatre, The Random Farms Kids' Theater, playing parts such as Dorothy Gale in The Wizard of Oz, the title role in Cinderella, Gertrude McFuzz in Seussical and Marion Paroo in The Music Man.
[3] At the age of nine, Damiano made her professional debut in New York City playing Samantha and Josefina in a show based on the American Girl dolls.
[3] On December 10, 2006, at the age of 15, she joined the original cast of the musical Spring Awakening on Broadway as an ensemble member and understudy for the roles of Anna, Martha, Ilse and Thea.
[4][5] After almost a year with the show, Damiano played her final performance on November 6, 2011, and was succeeded by Rebecca Faulkenberry of Broadway's Rock of Ages, from Nov.
[7] On November 9, 2015, it was announced that Damiano would return to Broadway (for the first time in four years) and reunite with Spring Awakening composer Duncan Sheik and Next to Normal co-star Alice Ripley in the musical adaptation of American Psycho in the role of Jean (as portrayed by Chloë Sevigny in the 2000 feature film of the same name).
[8] In December 2019, it was announced that Damiano would star alongside Ana Nogueira, Joél Pérez, and Michael Zegen in the world premiere of the screen-to-stage adaptation of Bob & Carol & Ted & Alice by The New Group.
In his review in The New York Times following the 2009 Broadway opening, Ben Brantley observed, "The notion that personality is fragile, always on the edge of decomposition, is exquisitely reflected in Ms. Damiano’s astringent, poignant Natalie".