He immigrated to the American Colonies in 1698 and lived in Boston for several years before moving to Newport, where he set up shop at 30 Thames Street in 1705.

He taught at the Rhode Island School of Design and, along with his business partner, Graham Carey, published the instructional book The Elements of Lettering in 1940.

In 1964, he was commissioned to design and carve the inscriptions for the John F. Kennedy Memorial in Arlington National Cemetery.

He carved gravestones for Tennessee Williams, Lillian Hellman and George Balanchine; designed and carved inscriptions for the Prudential Center in Boston, the Boston Public Library, the National Gallery of Art, the Dallas Museum of Art, the Chicago Mercantile Exchange Center and the Armand Hammer Museum of Art in Los Angeles; and carved the date stones of the Vietnam Memorial in Washington, D.C.

In 1993, he turned over the business to his son Nicholas Benson, who continues to produce hand-carved inscriptions in stone.