In 1995, he co-founded DoubleClick (acquired by Google for $3.1 billion) and served as Chief Technology Officer for 10 years. Dwight was the architect of the DoubleClick ad serving infrastructure, DART, which serves tens of billions of ads per day.

Earlier he was Co-Founder, Chairman, and the original architect of Panther Express (merged with CDNetworks), a content distribution network (CDN) technology. Dwight is also a Co-Founder of, and investor in, Business Insider and Gilt Groupe.