Bateman spent the next five years with F. R. Benson's Shakespearean touring company, playing increasingly important roles, including Titania in A Midsummer Night's Dream and Celia in As You Like It.

There she played a variety of leading roles in such works as The Little Minister, a comedy by J. M. Barrie, Secret Service, a serio-drama, and Under the Red Robe, a romantic drama.

She joined Gerald du Maurier in 1906 as Gwendoline Conran in Raffles at the Comedy Theatre, which ran for 351 performances, perhaps her greatest success to that date.

She appeared in a revival of The Whip, by Cecil Raleigh and Henry Hamilton, at Theatre Royal, Drury Lane in 1910 (in which she rode a horse astride).

Playgoer and Society Illustrated wrote, "It would be difficult to find a sweeter Lady Diana Sartorys than Miss Jessie Bateman".