Nick Benson began working in his family business, The John Stevens Shop at age fifteen for his father, John Benson. He studied Drawing and Design at State University of New York at Purchase in 1986. Benson spent 1987 at the Schule für Gestaltung Basel in Basel, Switzerland where he studied calligraphy, type design, typography, and drawing under Andre Gurtler, Christian Mengelt and Armin Hofmann.
He returned to the U.S. in 1988 and continued to work under John Benson in The John Stevens Shop. His father passed on the business to him in 1993. Benson expands the traditional arts of hand lettering and stone carving through his designs. He is also committed to teaching young artisans, in the hopes that they will go on to create their own works and thereby ensure that the legacy of this centuries-old artistic practice endures. He has had several design students, especially from nearby Rhode Island School of Design, and apprentices work with him in the shop and on projects.
Benson has created a distinctive architectural lettering for these architectural and monumental commissions, with careful attention to the effects that large scale, shifting light, and long-term weathering have on the letters, as well as carefully crafting very small details of each letter. “The entire composition is key,” he explained in an interview with the architectural historian Judith Dupré, “but the proportion of the letter, the design of the particular letter form itself, is extremely important too. Equally important is the cadence of the text, how the negative space is used, word spacing, line spacing—all of that is absolutely crucial to good inscriptional carving.”  He developed an original font that draws on both classical Greek letter forms and contemporary sans serif lettering for the Martin Luther King, Jr. Memorial, on the National Mall.
Benson's work at The John Stevens Shop has also included personal gravestones and tomb markers. Benson's father, grandfather and his predecessors at the Shop have created individual gravestones on materials including grey slate and Rhode Island granite.
- "Nicholas Benson - Stone Carver". Retrieved 29 September 2010.
- "The John Stevens Shop". Retrieved 29 September 2010.
- Anne Harding, 'Carving His Niche' Boston Globe, 1996
- Judith Dupré, “Interview with Nicholas Benson,” Monuments: America’s History in Art and Memory (New York: Random House, 2007): 141.