He had a sister (Ellen), a brother (James Duncan), and four half-brothers on his father's side (Geoffrey, Richard, Philip, and Jonathan).
[1] After being released from the military, Hayward began a career in Vermont as a senior analyst/programmer at National Life Insurance Company, where he worked until February 1974.
[1] While working at National Life Insurance Company, Hayward became involved in local politics, eventually serving on multiple committees from the town to state level.
In 1978, Hayword was asked to consider replacing the Vermont Republican State Committee's chairman James Mullin, but declined to do so.
[3] Hayword then served as the president of the Vermont Bankers Association, a position he held until 2002, at which point he rejoined Snelling's executive team.