In 1983, Westly became the New Business Manager at Sprint Telecommunications. In 1986, he became an investment banker at Valentine and Company (later called Bridgemere Capital) in San Francisco. In 1988, Westly became President of Codd & Date, a leading relational database consulting & services firm. In 1991, Westly became the Deputy Director of the City of San Jose Office of Economic Development and began teaching at the Stanford Graduate School of Business, a position he held for the next five years.