[8] The album consisted of jazz-pop cover versions of traditional pop songs by Cole Porter, the Gershwin brothers, Kurt Weill, and José Luis Perales.

Shepherd's album The Signal (2014) consisted of ten original songs on topics as varied as motherhood, Monsanto, witchcraft, and war, and featured guests such as Benin-born guitarist and composer Lionel Loueke and drummer Larnell Lewis.

By far her edgiest and most hip work to date, it features collaborations with Danish bassist Jasper Hoiby and Canadian guitarist Michael Occhipinti.

She has also shared the stage with the likes of Bonobo, Five Corners Quintet, Victor Wooten, Spankie Wilson, the JazzCotech Dancers, and the Quantic Soul Orchestra.

She has appeared as a guest vocalist / pianist on albums by various artists, such as MC Abdominal, Peter Appleyard, Michael Occhipinti, Andrea Superstein, Drumhand, and Circle Research.

With Robert Glasper, Esperanza Spalding and Jose James, Shepherd is credited with invigorating the vocal jazz song and bringing jazz-influenced music to a younger audience.

[9][10][11] Real Detroit Weekly has called her "a jazz virtuoso blessed with a pop sensibility",[12] while Mojo Magazine has described her "an intellectual Esperanza Spalding".