After graduating with a degree in accounting in 1983, Randy started his career with an internship in the Washington, D.C. office of the former Arthur Andersen. After earning his designation as a certified public accountant, he left public accounting to work for a firm specializing in third-party computer maintenance. Working for this firm, he spent time with computer engineers, honing his understanding of the technology. Randy eventually found his niche at his hometown company, Everett Cash Mutual Insurance Company (ECM Insurance Group), and rose to become president & CEO in 1998.

As president & CEO, Randy was inspired to change ECM’s direction; the organization was started by farmers but had strayed away from that being its focus. In 2002, Randy put a new plan in place for ECM, shifting from being a generalist writer of property and liability coverage to concentrating on farm and agricultural insurance. Since then, the organization has grown from two states to 10, and from $8 million in net worth to $64 million.

Randy was elected to the AAIS board in 2014.