[3] In 1982, Jebb was commissioned as a military intelligence officer in West Point's Department of Social Sciences and went on to work in the National Security Agency (NSA).

During 2000–2001, she was U.S. Military Academy Fellow Naval War College, teaching strategy and force planning.

It was reported on June 16, 2016, that President Barack Obama appointed Colonel Jebb to the position of dean of West Point, replacing Brigadier General Timothy Trainor.

[4] She retired from military service and relinquished her position as dean to a newly promoted brigadier general, Shane Reeves, on May 28, 2021.

[5] On March 5, 2021, it was announced that Jebb would be Ramapo College's fifth president, succeeding Dr. Peter Philip Mercer.