A member of the prominent Billings family, he was notable for his investment stakes and management roles in several Vermont businesses.

[1] Billings worked in the mercantile business at the San Francisco warehouse of Simmons, Hutchinson, & Co., and was briefly employed to book passage for travelers and transport of cargo on a Sacramento River steamboat, the Jenny Lind.

[1] Shortly after arriving in Woodstock, Billings and a cousin traveled to Freeport, Illinois to explore business opportunities.

[1] Billings constructed a store as part of Woodstock's newly built Phoenix Block commercial building, and his new venture opened in April 1861.

[1] Other business endeavors in which Billings was involved included promotion of the Woodstock Railway, of which he was an original incorporator and served as president.

[1] Billings also served on the board of directors of the Woodstock Hotel Company and Norman Williams Public Library.

[1] When the Rutland and Woodstock Railroad Company was incorporated in 1882, Billings was one of two commissioners empowered to execute the corporation's initial stock subscription.

[13] Locations with connections to Billings are included in the Woodstock Village entry on the National Register of Historic Places.