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Jerry Holcombe has a diverse work experience in various roles. Jerry started their career as a Manager at the University of Manitoba in 1992 and worked there until 1997. Following that, they worked as a Consultant at Information Development and Training from 1997 to 2002. Jerry then joined the Province of Manitoba as a Manager of Information Systems from 2002 to 2005. Since 2005, Jerry has been working at Online Business Systems, initially as a Senior Consultant and then progressing to roles such as Principal Consultant, Director - Engagement Management, and currently serving as the Senior Director - Governance, Risk, & Compliance since February 2022.

Jerry Holcombe attended Milton High School, but the start and end years are not provided. After high school, they attended the Georgia Institute of Technology from 1984 to 1988. Jerry then went on to study at the University of Manitoba from 1989 to 1993. Jerry Holcombe has also obtained certifications including PCI-QSA from the PCI Security Standards Council and certifications such as CISSP, CTPRP, and PMP from various institutions.