Trujillo has a Bachelor of Business degree (BBus) and an MBA from the University of Wyoming.
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In November 2000, he became chairman and CEO of Graviton, remaining until that startup closed.
In 2003, he became CEO of Orange SA, where he had served as a board member since 2001. He held that position until March 2004.
He was appointed Chief Executive Officer to Australian telecom giant Telstra Communications on July 1, 2005.
During the period of Trujillo's tenure, Telstra's share price underperformed the market by around twenty percent, losing over $25 billion in valuewhile customer complaints rose 300 percent. Major factors in the company's share price decline were the global financial crisis of 2008–2009 and being disqualified for submitting a non-compliant bid to the National Broadband Network tender issued by the Rudd Government.