Be a Leader by Listening to Employees and Clients

During the past 60 years, Milwaukee-based Robertson Ryan Insurance has grown from a small, local independent agency into a Top 100 firm employing some 150 agents and 385 associates. But employees say that despite its growth over the years, the agency hasn’t lost its family-style culture in which employees feel valued, heard, and supported.

This year, Robertson Ryan won Insurance Journal’s Overall Best Agency to Work For, an annual awards program where thousands of independent agency employees nominate their organizations, nationwide.

“Robertson Ryan gives you a voice. They listen, encourage, and are there for all of their employees,” said one person when nominating the agency.

Another employee added: “I have worked here for over nine years, and it’s the best place I have ever worked at. Management is very good, you feel heard, and additional education is always available if wanted.”

The recognition as a “Best Place to Work” is not new for RRI. The privately owned agency has been recognized as a top workplace for years, including as Insurance Journal’s Gold Award BATWF winner for the Midwest in 2024.

“We are a national agency, meaning we are big, yet operate like a smaller company, meaning we have the resources to take care of our team, but done in a way that is genuine with personal touches,” said Allan Degner, senior vice president of marketing and communications. “We support a flexible work culture, offering remote, hybrid, and office work, generous PTO and holidays, health benefits, profit sharing, and an environment where people are encouraged to grow professionally and personally.”

Degner said that people stay with the agency because they see meaning in their work, and the leadership shows their employees just how much they are valued and supported.

There are several reasons RRI is unique from other agencies, Degner said. First, each agent owns their book. “That means they have a personal stake in their clients, direct responsibility, and ownership of their professional path,” he said. “This model brings commitment, accountability, and entrepreneurial spirit.”

Employees and agents don’t just sell policies. Everyone plays a part as the clients’ trusted advisor, Degner added. “Our guidance, resources, and year-round partnership set us apart as accessible, long-term partners who care.”

And even as the firm has grown, agency leadership maintains a focus on culture and values.

“At Robertson Ryan, we’ve been intentional about building a culture that thrives on flexibility, engagement, recognition, and support,” Degner said. “From our Employee Engagement Committee to our Charitable Foundation, and from career development to overall well-being, these commitments are woven into our identity and daily operations and are not treated as afterthoughts.”

One employee told Insurance Journal: “One of the things I’m most proud of at our agency is the way leadership consistently backs up their words with action when it comes to supporting employees and clients,” they said. “For example, when our team faced an unusually heavy renewal season last year, management stepped in with extra resources, flexible scheduling, and direct involvement to make sure no one felt overwhelmed and every client received top-tier service.”

That balance of care for both employees and clients captures what makes this agency special, another employee said.

“One major thing that separates us is we have a floater department. They can jump in and assist you if you are falling behind, or they can cover your book while you are out on leave, or just vacation. That service allows us to feel like we can actually take time off,” they said.

Being a “Best Agency to Work For” starts with leadership and listening, Degner said.

“Leadership isn’t about having all the answers; it’s about asking the right questions, clearing obstacles, and helping others succeed,” he said.

“It’s about creating an environment where people feel valued, respected, and empowered.”

His advice to other agency owners today:

• Empower people and give them ownership. An ownership mindset builds investment.
• Be flexible and deliver an environment where work-life balance matters.
• Make connections by holding regular employee gatherings–virtual or in person.
• Give back to the community.
• Always support employee growth and learning.

Topics Leadership