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The Co-operators group auto and home insurance plans are administered by HB Group Insurance Management Ltd.

Brian Harriott and John Brown founded HB Group Insurance Management Ltd. in Winnipeg in 1979 with the goal of marketing group auto and home insurance programs to employer groups. In 1980, HB Group was purchased by Reed Stenhouse, an international commercial brokerage, and began expanding into other provinces. The change in ownership resulted in improved premium and service capabilities. HB Group quickly became a nationwide broker, providing sales and service in all 10 provinces.

In 1986, The Co-operators entered into a joint venture with Reed Stenhouse whereby The Co-operators provided resources in the areas of management, claims and underwriting. One year later, The Co-operators formed COSECO Insurance Company as the primary insurer for HB Group.

HB Group was sold to The Co-operators Group Limited in 1989 and became part of The Co-operators group of companies. As a member company, HB Group began forming partnerships with other innovative insurers, enabling it to be more sensitive in its pricing and more flexible in its plan design. New product lines are continually being launched to complement HB Group's auto and home plans.

In 2006, the decision was made to rename the auto and home group products as The Co-operators to complement the growing group benefits and financial services operation within The Co-operators group of companies.