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Diane Wesson has a strong background in development roles. Diane began their career in 1987 as the Director of Development for the American Red Cross, where they worked until 1993. From 1992 to 1995, they served as the Director of Community Relations for the Emergency Housing Consortium. In 1994, they became the Executive Director of the College Foundation at San Jose City College, a position they held until 1999. From 1999 to 2004, they worked as the Director of Development for Goodwill Industries of Silicon Valley. Diane then transitioned to a role as the Director of Development at Notre Dame High School, San Jose from 2004 to 2006. In 2006, they joined Family Supportive Housing as the Director of Development, staying until 2008. From 2008 to 2012, they held the same role at the Gardner Family Health Network. Most recently, they have been the Director of Development at EMQ FamiliesFirst since 2012.

Diane Wesson has attended San Jose City College and Los Angeles Pierce College. However, no specific details about the start and end years, degree name, or field of study are provided.