Greencastle superintendent Lori Richmond confirmed the resignation to the Banner Graphic.
No reason was given for Shepherd's resignation, just eight months after she was hired by the Greencastle School Board and only five months after her duties officially began.
Middle school principal Tamra Walker is set to replace Shepherd at the high school.
In Walker's place, assistant superintendent Dawn Puckett will take over at Greencastle Middle School.
No official action can be taken on the transfers until the school board meeting on Wednesday, Dec. 12, but Richmond said her recommendation that the board appoint Walker and Puckett to the new positions will be on next week's agenda.
If approval is made, the administrators will take over their new duties on Wednesday, Jan. 2.
Assistant principal Russ Hesler will take care of the principal's duties for the remainder of the semester.