Winston has been crafting software professionally for over a decade at Fortune 500 companies Electronic Data Systems and Borders Group Inc. He has worked on a wide variety of large systems, including Billing & Accounts Receivable, Warehouse Management, and E-Commerce. Before founding Radberry, Winston lead teams in the development of several E-Commerce systems, as well as taking responsibility for major Fortune 500 web sites. Winston in an active member of the SouthEast Michigan Ruby community as an organizer and speaker. He formed the MidWest Ruby Brigade to give groups in the region a larger sense of community. Winston is a co-organizer of the 2nd Annual Great Lakes Ruby Bash.