After ill health forced her to stop teaching, she began to pursue librarianship, as she was intrigued by the work of the newly-organized American Library Association (founded in 1876).

In 1884, she worked at a small country library, after which she contacted Melvil Dewey, then-librarian of Columbia College, about library-related employment.

In 1887, Dewey opened the Columbia College School of Library Economy, the first librarian training institution in the United States, and hand-selected Cutler as a cataloging instructor.

She also oversaw the expansion of the scope of library training to better suit public service as professional educators, her ideal of the librarian.

As an exhibit committee chair for the World's Columbian Exposition in 1893, she established and compiled a catalog for a model library with 5,000 volumes.

[2] Though her professional activities after 1905 were limited, she continued to contribute to the field through articles she wrote and submitted to journals,[1] as well as through lectures and presentations she gave on book selection and the history of libraries.

In addition, women did not hold positions offering the highest salaries, but rather appeared to perform the same level of work for less compensation.

Cutler Fairchild did find agreement among the criticizers that positions requiring "gracious hospitality" were held more successfully by women including the head of small or medium-sized libraries and all work with children.