Robertson Ryan Insurance builds loyalty through belonging and autonomy

Robertson Ryan Insurance received dozens of nominations for the annual Best Agency to Work For award and won this year’s Bronze prize for the Midwest region.

The Milwaukee, Wisconsin-based agency has spent more than 65 years building a culture designed to help employees bring their best selves to work. Christine Rogers, senior vice president of customer service, said the company has worked deliberately to keep that culture personal as the organization grew.

What has sustained employee belonging?

The agency’s culture rests on a workable mechanism: personal connection at work, practical support for employees’ lives and room to solve problems together with colleagues. Rogers described the operating challenge plainly: insurance work can strain customer service, while employees still need a collaborative place to solve problems.

“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.”

Allan Degner, senior vice president of marketing & communications, treated the nomination response as the agency’s strongest endorsement.

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

Employee nominations highlighted four recurring features:

• A benefits and compensation structure that employees commended.
• The ability to work remotely and take time off to be with family.
• Constant professionalism from company leaders.
• A family-like atmosphere that made employees feel connected.

Many respondents called Robertson Ryan the best insurance agency they had ever worked for. One employee credited the agency with caring for staff, the business and the community.

“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.”

What keeps people in the agency?

Employee accounts connect the agency’s retention appeal to practical flexibility, sustained career length and leaders who listen closely before correcting problems that affect daily work. One employee left retirement and returned to Robertson Ryan after a decades-long career in insurance. The employee said they felt more respected for their talents and knowledge there than anywhere before.

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

Multiple employees described accommodations for recovery from a cancer diagnosis and care for a parent in hospice. Employee accounts put well-being outside work at the center of the workplace. A happier, healthier team creates the foundation on which individuals can thrive. Other employees described starting or growing an insurance career and then staying at Robertson Ryan for many years, in some cases for decades.

Why does independence matter?

Against a backdrop of mergers, acquisitions and private equity, Robertson Ryan has stayed true to its roots. One producer described a balance that gives employees control while preserving the resources, support and stability of a large agency.

“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.”

The producer’s account describes a two-part model: individual control over business development and shared resources, support and stability available to producers within a larger organization. That structure gives producers room to run their businesses while drawing on agency resources, support and stability.

What does leadership contribute?

Robertson Ryan’s leadership team equips employees with tools to succeed and creates room for staff to speak up. Rogers said recognition and communication are central to how leaders show care.

Her point makes culture operational: notice contributions, communicate directly, accept imperfection and listen when problems remain, so employees can see genuine concern from their leaders.

“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.”

Her focus on small actions matches what employees described: leaders notice work, remain professional and listen. Another employee tied the agency’s reputation to the same operating choice.

“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.”

The next test for Robertson Ryan is whether this operating model can keep experienced employees engaged for decades while attracting more referrals from current staff. That outcome will depend on the same combination described in the nominations: belonging, autonomy, practical support and visible recognition.