After leaving the Army, Greenfield took up work in the then-nascent field of information architecture for the World Wide Web, holding a succession of positions culminating in employment at the Tokyo office of Razorfish, where he was head of information architecture.
In the 2006 and 2007 academic years, with Kevin Slavin of New York design practice area/code, he co-taught a class at New York University's Interactive Telecommunications Program called Urban Computing. In the following academic year this class was renamed Urban Experience in the Network Age and Greenfield taught it alone.
From 2008 to 2010 he was Nokia's head of design direction for user interface and services, residing in Helsinki throughout the assignment. In 2010 he returned to New York City and founded an urban-systems design practice called Urbanscale, which describes their work as "design for networked cities and citizens." In September 2013, Greenfield was awarded the inaugural Senior Urban Fellowship at the LSE Cities centre of the London School of Economics, relocated to London, and subsequently taught in the MArch Urban Design programme at the Bartlett School of Architecture of University College London.
Greenfield is credited with having coined the word "moblog" to describe the practice of publishing to the World Wide Web from mobile devices, and having organised a conference devoted to discussing this practice in Tokyo in mid-2003.
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