Best Agency to Work For – Midwest Gold Winner: Robertson Ryan Insurance

What makes Robertson Ryan Insurance a great place to work?

The freedom to do the job, do it well and still have the time and energy for the life you want to lead, according to folks who work for the agency.

“Robertson Ryan is a great agency to work for. They are very flexible, and there is no micromanagement that takes place in this agency,” said one employee responding Insurance Journal’s annual Best Agencies to Work For survey. “The agency is all about family and health and taking care of you.”

Robertson Ryan has been selected as IJ’s 2024 Gold Best Agency to Work For in the Midwest based on employee submissions to the survey.

Headquartered in Milwaukee, Wisconsin, the agency employs approximately 390 people who work in the office, from home or as hybrid workers. The agency adopted the flexible work model long before the COVID-19 pandemic forced businesses to expand their work definitions, said CEO Chris Illman.

“The company has 140 brokers/agents, and our uniqueness is that they all own their own book of business,” he said. “They care so much about their clients, they are forward-thinking and entrepreneurial.”

Employees cite this flexibility and dedication to work/life balance as a top reason the agency is a great place to work.

Investing in the right people is also a critical factor.

“We have a phenomenal HR department, and they are viewed as employee engagement,” Illman said. “They are truly viewed as a partner to the employee, to make their job easier. Our HR has taken on a great people leadership role versus traditional HR.”

The company sees less than 3% annual turnover, and that includes retirement, Illman said. And RRI’s renowned culture makes it easy to fill openings with top talent.

“Attracting talent starts with knowing we are flexible,” Illman said. “You have to be able to fit into what a really good new hire wants. We’ll adapt to what that employee wants and needs and get them into the right role.”

RRI’s remote work opportunity is one of the best, said one nominating employee.

“With plenty of the industry’s workforce being forced into and then out of remote work due to COVID, RRI continues to see the value in finding the right people to hire for their remote positions,” they said. “Their training, set-up, and support for their remote workforce is what makes them far better than other remote arrangements I’ve worked for in the past. Despite being a remote worker, I still have all of the same opportunities as those in-house employees.”

Employee engagement is designed to support growth and success, they added. “Regular company-wide virtual conferences that have nothing to do with insurance have been extremely successful, fun and much needed in this hard market. There has never been a time where I didn’t feel valued or respected as an employee with Robertson Ryan.”

With employees working remotely, hybrid and in the office, it can be a challenging balancing act, Illman said. “It’s not easy — there are different needs and wants with each of those groups,” he said.

“You’ve got to roll up your sleeves and do the tough things,” he added. “They know they are empowered, that they work independently, that we’re open and flexible, pay the right wages, offer great benefits and make sure they keep getting better year after year.”

Employees are proud that the agency has garnered other awards for its work culture, as well. “Winning Top Workplace by the Milwaukee Journal Sentinel for 2023 and 2024 says it all,” said one employee. “Winning a top spot like this not once, but twice, proves the positive culture at RRI isn’t a flash in the pan; rather, it is a philosophy that is embedded in the company’s fabric and influences the way RRI operates internally with employees and externally with customers.”

It was the relationship side of the business that drew Illman to insurance, he said.

“I love that it is relationship-focused — clients, employees, carriers. I think it’s one of the greatest industries in the world.”

Building the right team and company culture just makes it that much better. “Treat people the way you want to be treated, give them the right tools, let them know they are valued,” he said. “It’s somewhat a cliche, but if you are committed to taking care of your employees, they will take care of the clients. You’ve got to walk your talk.”