During his tenure, Sherman has been responsible for the creation and development of new media projects, such as the Downstage Center podcast and the original video series In the Wings, reformulation of The Wing's grants program, the redevelopment of the organization's website and the creation of programs for aspiring and early career theater professionals. In addition, he has served as the group's primary representative in all aspects of The Tony Awards, which The Wing established in 1947.

Regarding his decision, Sherman has said " I do not have a new job on deck, but feel it is appropriate to make my intentions known now, rather than surreptitiously seek work and, in doing so, potentially undermine the work of The Wing. I look forward to exploring what is yet to come, but in the meantime, I am committed to serving out the term of my agreement through the 2011 Tony Awards and insuring the smoothest possible leadership transition for the organization."