The cooperative efforts of Jessica Helfand and William Drenttel, Winterhouse is a design studio, institute, publisher and foundation rolled into one. Their work takes them in many different directions and they have been very successful in most, if not all, of them. Both Helfand and Drenttel claim the title of graphic designer, among other things, Drenttel is a publisher and Helfand a Writer. The work that comes from the design studio facet of their organization includes website, book, poster, editorial and identity design.

In 2003 they established Design Observer, which was a wildly popular online resource for design writings, opinions and discussions. They have published many materials under their publishing guise of Winterhouse Editions and been involved in a host of other projects including a poetry foundation, a network of organizations who are trying to expand the educational opportunities in their own countries called Teach For All, and personal photography projects . Their wide range of work keeps them very active within the design, art and architecture circles and they are constantly giving lectures about their work at a variety of different gatherings and conferences.