Raymond began her career performing in
variety theatre as a member of the burlesque troupe of Rice & Barton. In January 1889 she performed in a variety benefit concert given to raise funds for the Eastern District Hebrew Free School in Brooklyn. In November 1889 she was performing in the play
Oklahoma Nick at the Grand Museum; a
dime museum in New York City. By February 1890 she was performing in a variety show at another New York City dime museum, Huber’s Palace Museum, which was owned and operated by George H. Huber (1843-1916). That same year she went to work as a singer in another one of Huber's business ventures, Huber & Gebhardt's Casino. In January 1891 Raymond was performing in
vaudeville at the Winter Garden Theater in St. Louis, Missouri with the
St. Louis Post-Dispatch describing her as a "talented and pretty baladiste". By the following March she was back in New York performing in a variety show at Feltman's Tivoli Theatre .
The Brooklyn Daily Times review described her as a "serio-comic vocalist and
soubrette. Later in the year she was performing in vaudeville in Ohio before joining the
burlesque theatre troupe Turner's English Girls as the company's primma donna. She performed with this group in theaters in Kansas, and Texas. By the end of November 1891 she was back in Brooklyn performing in a minor part in the premiere of
Henry Grattan Donnelly's farce
A Pair of Jacks at the Bedford Ave Theatre. By the end of the year she was performing as a member of Rose Hill's English Folly Company in Rhode Island; and remained with the company on tour for performances in theaters in New York, Pennsylvania, Kentucky, and Ohio in 1892. In September 1892 Raymond performed for the re-opening of the newly renovated Shea's Music Hall in Buffalo, New York. That same month she joined the theatre troupe of
Joseph J. Sullivan playing the soubrette part in
The Black Thorn in Connecticut. In October 1892 she appeared in concert with the band of the
United States 23rd Infantry Regiment for performances in Brooklyn. She spent the remainder of the year touring the United States in the farce ''Bill's Boot'' with a cast that included actor Joseph J. Sullivan and the
Russell Brothers female impersonators. She remained with that production through February 1893, and then toured in vaudeville with the Meteor Specialty Company. In April 1893 she appeared on
Broadway in a variety show given at the
Imperial Music Hall that was headlined by
Matthews & Bulger. Later that same month she performed with
Weber and Fields in their show at the
Park Theatre, Manhattan, and then proceeded to tour with them to St. Louis. In the summer of 1893 Raymond starred in the farce
My Uncle for performances at the Eighth Street Theatre in Philadelphia. She then joined the burlesque troupe of
Sam T. Jack for performances at the
Lyceum Theatre in Boston before rejoining the Meteor Specialty Company on its tour in the vaudeville circuit beginning at the end of September 1893. By November 1893 she was performing as a member of Harry Williams's "Own Company". This was followed by tours with the Irwin Brothers Company and the Henry Burlesque Company in 1894. In the summer of 1894 she returned to New York City to perform at the American Theatre Roof Garden with a cast that included
Andrew Mack. After this she joined the theatre company of Boston's
Howard Athenaeum with whom she toured to Broadway's
Tony Pastor's 14th Street Theatre in the autumn of 1894. She also performed with the company at
Albaugh's Grand Opera House in Washington D.C. and the
Chestnut Street Opera House in Philadelphia in September 1894. ==The Rogers Brothers and Broadway==