She was nominated for the Tony Award for Best Featured Actress in a Musical in 2015 for playing the role of Medium Alison in Fun Home.

[3] Skeggs graduated from Fiorello H. LaGuardia High School in 2008 and from Emerson College in 2012 with a degree in theatre and minor in writing.

[6] Skeggs played Rebecca in the Huntington Theatre Company (Boston, Massachusetts) production of Our Town in December 2012.

[10] Skeggs was the understudy in the Off-Broadway production of Fun Home in 2013 for the roles of Joan and Medium Alison.

She replaced Alexandra Socha (who departed the show for personal reasons) in the role of Medium Alison in November 2013.