Squerciati made her Broadway debut in an adaptation of Ernst Lubitsch's To Be or Not to Be, directed by Tony Award winner Casey Nicholaw.

Squerciati created the role of "Kerri Taylor" in the a cappella musical comedy Perfect Harmony, and was a member of The Essentials.

After appearing in guest roles on The Good Wife, Damages, Blue Bloods and Law & Order: Special Victims Unit in 2010 and 2011, she gained attention in the fall of 2011 in an 8-episode arc on the fifth season of Gossip Girl.

[9] On February 15, 2017, Squerciati announced her pregnancy via Twitter; she gave birth to a daughter in May.

[11] In September 2019, court documents alleged that Squerciati was the child of the late financier John R. Jakobson (who was also the father of actress Maggie Wheeler[3]), and that while she was allegedly promised to be named in the mogul’s will, no provision was made for her.