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Derek Woolf has a strong work experience in various roles in the technology and financial sectors. Derek started their career at Washington Mutual as a Customer Service Representative II from September 1995 to September 1999. Derek then joined Accent Computer Solutions, Inc. in August 1999, where they served as the Chief Operating Officer until May 2023. Currently, they are working at VC3 as the Interim Chief Operations Officer since December 2022, and they will transition to the role of Chief Operating Officer from May 2023 onwards.

Derek Woolf attended the University of La Verne from 1998 to 2000, where they obtained a Bachelor of Science degree in Accounting.