Henry Clay Conner Jr. founded Conner Insurance in 1949 after attending school through Aetna Insurance following his service in WWII. He started the business in a mall basement, initially offering property, casualty, and life insurance. His dedication to quality service, emphasis on relationships, and innovative design laid the foundation for the firm's future success.

In 1973, Clay, Jack, Jim, and Tom Conner acquired the business from Henry. At the time, Jim was a junior at Indiana University, Tom was a junior in high school, Clay was a stockbroker, and Jack was the only one working in the business. The company, with $150,000 in annual revenue, primarily from commercial insurance, thrived under their leadership. By the time they sold it in 2015, after 42 years, they had expanded its offerings to include Group Health Benefits, Wellness Services, and Personal Lines, growing the revenue to $4 million.

Today, Ben Conner, Todd Hufford, Ryan Spencer, Josh Conner, Annie Spencer, and Zack Conner, the third generation, continue to carry this family business with excellence, building on the legacy of innovation and dedication established by their predecessors.