 Beginning as the principal of Greenwood High School from 1911 until 1915; Willey became secretary to U.S. Representative Thomas W. Miller in Washington, D.C. from 1915 until 1917 and State librarian from 1917 until 1921.Having been admitted to the Bar he was appointed deputy attorney general and prosecuting attorney for Kent County, Delaware from 1921 until 1931, Judge of the Court of Common Pleas of Kent County from 1931 until 1939, and Judge of the juvenile court of Kent and Sussex Counties from 1933 until 1939.Willey was Secretary of State from 1941 until 1943 and served as a trustee of the University of Delaware, of the Elizabeth W. Murphy School for Orphan Children, and of the State College for Colored Students.