hˈɪlɪɚd wˈɜːkt æt ðɪ oːɹɡˈoʊniən fɹʌm nˈaɪntiːnhˈʌndɹɪd fˈɪfti tˈuː tə nˈaɪntiːnhˈʌndɹɪd nˈaɪnti fˈoːɹ, stˈɑːɹɾɪŋ æz ɐ kˈɑːpi bˈɔɪ, ænd ðˈɛn ɹˈaɪzɪŋ tə klˈɜːk, spˈoːɹts ɹᵻpˈoːɹɾɚ, ɹᵻlˈɪdʒən ænd dʒˈɛnɚɹəl ɐsˈaɪnmənt ɹᵻpˈoːɹɾɚ, ænd ɪn nˈaɪntiːnhˈʌndɹɪd sˈɪksti fˈaɪv ɐsˈɪstənt sˈɪɾi ˈɛdɪɾɚ.
Hilliard worked at The Oregonian from 1952 to 1994, starting as a copy boy, and then rising to clerk, sports reporter, religion and general assignment reporter, and in 1965 assistant city editor.