[3] She graduated from the Fairmount School in Monteagle, Tennessee,[7] and, under the name Viola Roseborough,[1] briefly pursued a theatrical career with the Shook and Collier Company.

[11][1] At McClure's, her subordinates included Sonya Levien, who she is credited with having "mentored", [12] Willa Cather (who Roseboro' may have hired,[13] or caused to be hired)[10] and Witter Bynner, whose first poems were published in McClure's with her approval; Bynner subsequently described his job as delivering manuscripts from the editorial office to Roseboro's apartment.

[10] Her discoveries included Jack London,[11][2] Booth Tarkington[13] (whose The Gentleman from Indiana she described as having been "sent by God Almighty"),[15] and William Sidney Porter, from whom she bought the first story under the pseudonym "O.

[3] Similarly, literary scholar Elizabeth Ammons has speculated that Roseboro's 1907 short story "The Mistaken Man" "provided the spark for" Cather's 1912 novel Alexander's Bridge.

[16] Roseboro' continued writing her own fiction even after becoming an editor, including the novels The Joyous Heart (1903) and Storms of Youth (1920), and the short story collections Old Ways and New (1892) and Players and Vagabonds (1904).