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Rob Olsen has a strong background in operations and sales engineering, with over 18 years of experience in the technology industry. Rob began their career at Rolm Mil-Spec Computers in 1982 as a Manager in Management Information Systems. Rob then moved on to Aspect Telecommunications in 1989, where they served as the Director of IT for seven years. In 1997, they joined Personic Software, Inc. as the Vice President of Sales Engineering and Product Management, holding this position until 2001. In the same year, they started working at Techworkers as the Vice President of Operations, a role they currently hold. Additionally, in 2002, they briefly served as the Director of Sales Engineering at Knowledge Planet. Throughout their career, Rob Olsen has consistently demonstrated their expertise in managing operations and sales engineering functions.

Rob Olsen attended Most Holy Trinity, the details of which are unknown. Rob completed their high school education at Yerba Buena High School from 1970 to 1975, focusing on general studies. Following this, they pursued a Bachelor's Degree in Accounting and Finance at San Jose State University from 1976 to 1980.