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Stitt co-founded Network Peripherals in 1989 and served first as its vice president of marketing, and then as vice president and general manager of the OEM business unit. Network Peripherals was the largest vendor of the Fiber Distributed Data Interface (FDDI) technology while it was popular in the 1990s.
In 1996, he co-founded Extreme Networks, and served as chief executive officer until 2006 (but continued as chairman of the board of directors). He said the company name referred to extreme skiing.
In 2001, Stitt was a national finalists and award recipient of the EY Entrepreneur of The Year Award.
Mark Canepa became CEO of Extreme in August 2006.
In June 2007 he joined the board of directors of Barracuda Networks.
In July 2009 he returned to Extreme Networks for a temporary market development role.
He was on the board of directors of RGB Networks through 2013, and the board of directors of Skyfire from 2006 to 2014.
In 2013 he became chief executive at Nebula.