Gerald Cole
CEO @Oliver Insurance Software
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WORK HISTORY
CEO @Oliver Insurance Software
CA
EDUCATION
Schulich School of Business - York University
Masters Diploma in Business Analysis
Capilano University
Bachelor’s Degree, Human Kinetics
British Columbia Institute of Technology
Web Page, Digital/Multimedia and Information Resources Design
The University of British Columbia
Bachelor of Human Kinetics, Sports Management
Vancouver College
High School
The University of British Columbia
Diploma in Accounting
SKILLS
ABOUT GERALD COLE
Gerald Cole is CEO of Oliver Software, a SaaS company delivering right-sized, modular platforms for insurance and group benefits. Under his leadership, Oliver is a trusted partner across the industry, helping organizations streamline administration and modernize member experiences. The platform also unlocks the value of data and enables the advanced distribution of insurance and benefits products. With nearly two decades of experience in technology, entrepreneurship, and the group benefits industry, Gerald focuses on solving complex challenges with practical, scalable solutions. He builds platforms that integrate seamlessly into the broader distribution and administration ecosystem, delivering measurable impact through collaboration, focus, and data-driven execution. Gerald chairs the board of Oliver Software and serves as an advisor to Eligeo CRM Inc. He is a tenured member of the Vancouver Chapter of the Entrepreneurs’ Organization (EO).
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