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A Systematic Approach to Growth

When you work for R&R Insurance, a Business Insurance Top 100 Agency, a million-dollar book of business is very achievable. Our strength is our organic growth.

We utilize industry-leading technology for lead generation and prospecting, B2B data resources and thousands of cross-sell opportunities.

Our in-house team of data analysts, claim professionals, loss prevention specialists, account managers and marketing experts help support you and provide exceptional customer service to your clients. As a member of Assurex Global, the world’s fifth largest broker, we pursue domestic and global accounts with worldwide expertise and local service.

We are proud to be one of the largest independently and family-owned insurance agencies in the country since 1975.

We are here to stay and not for sale. Come join us.



As a sales professional, you have access to a full suite of industry benchmarking tools, market trends and insights to support new client development.

How We're Different

R&R Insurance's number one investment is its people. Better employees mean better service to our clients.

From industry veteran to recent graduate, R&R Insurance is looking for the top professionals in Commercial Property & Casualty, Employee Benefits, Personal Lines, and Wealth Management.

What it Means to be Independent

R&R Insurance is one of the largest family-owned independent insurance agencies in the United States with strong regional, national, and global relationships. We aim to honor the company's proud history and continue to foster a family-friendly culture. 

Headquartered in Waukesha, Wisconsin we house additional offices throughout the Midwest with a growing presence throughout the United States. In an industry awash with mergers and acquisitions, R&R's financials have remained strong with our flag firmly staked into the communities we serve. We are not for sale and have our eyes set on continued growth. 

Independence means a lot to R&R, but to many employees it could be as simple as not having to go through 5 layers of red tape to get a notebook. We encourage innovative thinking and creativity and never set up barriers to stifle new ideas.

What We Do
  • We are the Knowledge Brokers™ and emphasize education for both clients and employees. We don't expect you to know it all on day one and will happily invest to get you to a level where you can confidently advise our customers.

  • Work as a team to solve a myriad of challenges advocating for our policyholders. 

  • Specialize in an industry-focused niche by joining one of our many internal practice groups. 

Ripp, David (2)-1

“R&R Insurance provided me with the tools I need to succeed in building a book of business. The flexibility in my schedule and excellent work life balance have solidified what a great company R&R is to work for.” - David Ripp


Sherfinski, Shay

“It’s just been a collective good experience at R&R and I think that’s important. When you go someplace and are part of a team you want every day to feel like a good experience, and that’s what I feel being at R&R.” - Shay Sherfinski

Award Winning Culture

  • A 37.5 hour work week

  • Dress-For-Your-Day dress code policy
  • Being a family-owned agency we understand and provide for a family-friendly culture offering a number of flexible work options

  • R&R is committed to building diverse teams where differences enhance our understanding and where everyone experiences a sense of belonging

  • We are proud to be the recipient of a host of awards from numerous organizations with recognition ranging from Best Place to Work to Business of the Year

Exceptional Benefits

  • Profit sharing, perk programs with local companies, health insurance, dental insurance, vision insurance, 401k, life insurance, and additional voluntary options
  • We offer meaningful work opportunities, phenomenal pay, and a long list of benefits in an environment that recognizes the need for work/life balance

  • Since its inception, R&R Insurance has maintained a steady growth trajectory and deploys incentives to attract and retain the best talent in the industry
Fugate, Olivia (1)

“Promoted from within after only a year of service, R&R has given me the chance to push my career into an exciting direction. The culture, great employee benefits, it's all a  perfect fit.” - Olivia Fugate


Ron Fontaine

“It doesn’t feel like the daily grind when I'm at R&R. Honestly, it feels like I’m coming in to hang out with my buddies.” - Ron Fontaine

Agency Recognition

We are proud to be recognized by local and national industry leaders for the quality work of our employees. 

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Diversity & Inclusion

R&R Insurance supports and encourages a diverse and inclusive workforce. We believe that a diverse workforce benefits not just R&R Insurance, but all of our associates and clients as well.