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She is portrayed by Gillian Barber.
Doctor Hess serves as the Head Mistress for the Kendricks Academy in England, used to train future Men of Letters. In 1987, Hess called Mick and Timothy into her office and forced one of them to kill the other to ensure that they would follow absolutely. She handed them a knife, and to Timothy's horror, Mick stabbed him with it.
30 years later in 2017, while acting as a British Men of Letters Elder, Hess informs Mick that they don't have time to convince the American hunters to join them. She orders Mick to "assimilate or eliminate" and arranges her lackey, Renny Rawlings, to keep an eye on Mick.
Mick returns to the headquarters later on to find Doctor Hess with Arthur. Unlike before, Mick openly defies the British Men of Letters' code of conduct and chooses the Winchester way of doing things. His change in alliance convinces Hess that Mick has gone rogue, so she orders Arthur to shoot Mick point-blank.
While standing over Mick's corpse, Hess announces that the Winchesters must be eliminated and their efforts in America are a failure. Later on, Doctor Hess orders Arthur to infiltrate the Men of Letters bunker so that they may know all that can about Sam and Dean.
Later, Doctor Hess coordinates an assault against the American hunters. However, before they can act, a group of hunters including Sam Winchester, Jody Mills, Roy and Walt attack the British Men of Letters compound, taking several losses but killing all of the British operatives.
After killing a hunter, Doctor Hess retreats to the control room where she desperately calls for extraction, but is unable to receive it. At that moment, the hunters break in and Doctor Hess tries to convince Sam not to kill her, revealing the escape of Lucifer to him.
Doctor Hess insists that the American hunters still need the British Men of Letters, but Sam refuses and shoots the computer Doctor Hess was communicating to Britain through. Calling Sam a bastard, Doctor Hess grabs her gun but is shot through the head by Jody before she can do anything.