Built on Belonging: How Robertson Ryan Thrives on a Family-First Culture

At Robertson Ryan Insurance, a strong sense of belonging allows employees to bring their best selves to work every day.

Creating such an environment doesn’t happen by accident. Over 65 years, the Milwaukee, Wisconsin-based agency has worked at developing a culture where team members can come together to solve solutions in an authentic, collaborative workplace.

“We have grown as an organization, but we have worked hard to maintain a personal, family-type atmosphere where people know each other and feel connected,” said Christine Rogers, senior vice president of customer service. “Insurance can be a challenging business, and customer service isn’t always easy, but we have an amazing group of people who truly care about our clients and each other. That makes a huge difference.”

Employees take notice when they feel supported. Robertson Ryan received dozens of nominations for the annual Best Agency to Work For award. The agency is the recipient of this year’s Bronze prize for the Midwest region.

To be recognized for the award by colleagues affirms that Robertson Ryan is a special place to work, said Allan Degner, senior vice president of marketing & communications.

“Having our employees share that in their own words is the strongest endorsement we could receive,” Degner said.

Employees who wrote in to nominate the agency commended the agency’s benefits and compensation structure, the ability to work remotely and take time off to be with family, the constant professionalism exhibited by company leaders, and the family-like atmosphere.

Many employees said Robertson Ryan is the best insurance agency they’ve ever worked for.

“They truly care about their employees and having a successful business,” one employee wrote. “They also care a great deal about the community and give back at every available opportunity. I have recommended many people to apply for jobs here; it is an exceptional working environment.”

Another employee came out of retirement to work for Robertson Ryan. After a decades-long career in the industry, the employee reported feeling more respected for their talents and knowledge than anywhere before.

“They just respect your knowledge,” the employee wrote.

One of the common themes from employee responses is the spirit of independence that pervades the agency. In an era of mergers and acquisition and private equity, Robertson Ryan has stayed true to its roots.

“As a producer, Robertson Ryan gives me something that is increasingly rare in our industry: the freedom and autonomy to build my business my way while still providing the resources, support, and stability of a large organization,” an employee wrote. “The culture is entrepreneurial, transparent, and relationship-driven.”

Robertson Ryan’s leadership team makes it a point to equip employees the tools to succeed and to create a space for people to speak up. Recognition matters, too.

“Pay attention to the little things,” said Rogers. “Recognize people for the work they do, communicate with them. You won’t always get everything right, but if your employees know you genuinely care about them, are willing to listen, that goes a long way.”

Robertson Ryan has built a reputation as being a place where employees not only want to start or grow a career in insurance but stay for many years if not decades. Multiple employees shared how the agency accommodated their life circumstances, whether recovering from a cancer diagnosis or tending to a parent in hospice.

The message comes through clear: Employees’ well-being outside of work matters. A happier, healthier team leads to a foundation where individuals can thrive at their jobs.

“What makes Robertson Ryan a great place to work is the people and the team culture,” an employee wrote. “There is a strong sense of cohesiveness and a genuine desire to see everyone succeed.”

Topics Leadership