Montgomery was born July 2, 1960, in Kansas City, Missouri. Montgomery's first role was on the soap opera One Life to Live as Samantha Vernon from 1976 to 1981. Her well-known film role is in the hit comedy film Revenge of the Nerds (1984) as Betty Childs; she reprised the role in the TV films Revenge of the Nerds III: The Next Generation (1992) and Revenge of the Nerds IV: Nerds in Love (1994). She also played Dr. Sally Arthur, M.D. in Earth Star Voyager (1988), and appeared in the comedy films Up the Creek (1984) and Stewardess School (1986), and the horror films Girls Nite Out (1982) and The Kindred (1987).
Montgomery appeared on multiple television shows, including Columbo, Magnum PI, Midnight Caller, Full House, Cheers and The Honourable Woman.

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