After her high school graduation, Szold taught briefly at her alma mater, the Western Female High School. Soon after, she entered upon fifteen years of service at the private Miss Adams' school where she drew upon her own broad education to serve as an instructor of English, German, French, Latin, mathematics, history, botany, and physiology. In addition to her home and school responsibilities, Szold, under the penname "Sulamith," began contributing a regular "Baltimore Letter" to the Jewish Messenger published in New York.

In her "Sulamith" articles and in articles contributed to other national Jewish publications, Szold entered into the current debates of the American Jewish community and began to find her own distinctive voice. Although some respondents dismissed her female voice as irrelevant, Szold's observations and critique of American Jewish culture garnered attention among American Judaism's intellectual leaders. Szold became the only woman elected to the publication committee of the newly formed Jewish Publication Society in 1888 and was one of only two women invited to speak at the Jewish Congress held at Chicago's 1893 Columbian Exposition.

By her early 30s, Szold had established the exhausting pattern of dedicated work that would mark her career as she immersed herself in teaching (both day and night), communal involvements with local and national societies, household responsibilities, essay writing, and assisting her father with his publications.