Demo

Support Specialist - Commercial Lines

R&R Insurance and Wealth Management Career Opportunities
Waukesha, WI Full Time
POSTED ON 8/21/2026
AVAILABLE BEFORE 10/20/2026

Commercial Insurance Support Specialist

Looking to start a professional career where you can learn a valuable industry, build real expertise, and grow over time?

R&R Insurance is hiring a Commercial Insurance Support Specialist to join our Commercial Lines Service team. This is an entry-level opportunity designed for someone who brings strong customer service and organizational skills but may be brand new to insurance.

You don’t need insurance experience to get started. We’ll provide the training, licensing support, and hands-on experience to help you learn the business and build a foundation for a long-term career at R&R.

What You’ll Do

As a Support Specialist, you’ll learn how a commercial insurance agency works while supporting the team that helps businesses protect what they’ve built. You’ll work alongside experienced insurance professionals and gradually take on more responsibility as your knowledge and confidence grow.

You’ll:

  • Support Account Managers and other members of the Commercial Lines team with day-to-day client service needs
  • Prepare insurance documents, process requests, and follow up on outstanding items
  • Learn commercial insurance coverages, terminology, carriers, and processes
  • Navigate carrier websites, our agency management system, and other insurance technology
  • Develop strong habits around accuracy, organization, communication, and follow-through
  • Prioritize incoming requests and adjust as needs and deadlines shift
  • Build the insurance knowledge and professional skills needed to continue growing within R&R

What You’ll Bring

Insurance experience isn't required. We’re looking for someone who is curious, dependable, and ready to learn.

Ideally, you’ll bring:

  • 1–2 years of professional, administrative, or customer service experience
  • Strong attention to detail and a commitment to getting things right
  • Clear written and verbal communication skills
  • The ability to stay organized and manage competing priorities
  • Comfort learning new technology, systems, and processes
  • A collaborative approach and willingness to ask questions and learn from others
  • A high school diploma or equivalent

Why Join R&R?

R&R is one of Wisconsin’s largest independent insurance agencies, and we’ve remained independent for more than 50 years. That gives us the ability to invest in our people, make decisions for the long term, and create opportunities for employees to build meaningful careers here.

As a Support Specialist, you’ll receive structured training and support as you learn the insurance industry, including assistance earning your Property & Casualty insurance license.

You’ll also enjoy:

  • A 37.5-hour workweek
  • Flex Fridays, including every other Friday afternoon off
  • Generous paid time off
  • Medical, dental, vision, and life insurance
  • 401(k) with company match and profit sharing
  • Company-paid licensing and continuing education
  • On-site fitness center and employee café
  • Sit/stand desks and a modern office environment
  • Employee discounts on personal insurance and local attractions

Salary.com Estimation for Support Specialist - Commercial Lines in Waukesha, WI
$60,394 to $76,073
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