Engstead was born in California, and began his career in 1926, when he was hired as an office boy by Paramount Pictures' head of studio publicity, Harold Harley.
In 1927, Engstead pleased his boss by arranging a photo session for actress Clara Bow with photographer Otto Dyar using an outdoor setting which was unusual at that time.
Engstead's creative direction of photographs of actress Louise Brooks led to a promotion to art supervisor, where he oversaw the production of Paramount's publicity stills.
He produced promotional material for many television personalities, including Pat Boone, Carmel Quinn, Donna Reed, Ozzie and Harriet, Eve Arden, and Lucille Ball.
Engstead closed his studio in 1970 but continued to accept special portrait and television assignments until his death in West Hollywood, California, in 1984 at age 72.