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Trainee - Customer Service Representative (Hartford, WI)

Robertson Ryan Insurance
Hartford, WI Full Time | Part Time
POSTED ON 6/27/2026
AVAILABLE BEFORE 7/25/2026

Recognized nationally as a Top Workplace and Top 100 US Insurance Agency!

Since 1960, Robertson Ryan Insurance has provided comprehensive solutions across Business, Benefits, and Personal Insurance. We proudly serve over 70,000 clients, from small businesses to major national accounts across various industries. With a team of more than 526 professionals and partnerships with over 150 insurance companies, we are the 44th largest Property amp; Casualty Insurance Agency according to the Insurance Journal. Our dynamic and enjoyable culture is a cornerstone of our success, with many team members having been with us for over a decade. It’s an exciting time to join our growing firm!

Customer Service Representative (Trainee):

As a Customer Service Representative in Commercial or Personal Lines, you will have the primary responsibility of managing customers' service needs. In this role, you will work with the account manager, prepare proposals, answer incoming phone calls, greet and direct insurance office visitors, enter change requests and endorsements, and maintain our agency management system with current information.

This is an onsite position in our Hartford, WI office. This position is Monday-Friday from 8:00am-4:30pm.
This role is a great opportunity for someone eager to learn, develop new skills, and grow within the organization. In addition to front desk and administrative responsibilities, the position offers exposure to the insurance business and opportunities for professional development and advancement over time.

Responsibilities of a CSR (Trainee):

  • Commercial and Personal Lines policy information collection
  • Distribute quotes to prospective customers and current customers with follow up to answer questions.
  • Maintain document retention and document uploads, as needed per carriers.
  • Assist clients with making coverage changes and complete all service requests for clients.
  • Provide billing support to customers.
  • Understand and discuss coverages with clients.
  • Develop good working relationships with the underwriters.
  • Ensure that client issues are efficiently handled with resolution.
  • Email personal policy documents, as needed.
  • Answer office phone, assist customer thoroughly and direct call to appropriate person, if needed.
  • Establish and preserve a solid business rapport with clients.
  • Maintain accuracy in agency management system, quoting system, and carrier systems.
  • Additional office projects, as needed.

Required Qualifications (within 6 months of hire):

  • Willing to train the right candidate with excellent customer service and must be willing to get a Property amp; Casualty Insurance License within 6 months of hire.
  • Must be willing to work full or part-time in office at our Hartford, WI location.

Requirements of a CSR (Trainee):

  • Ability to operate various computer programs (Microsoft Office Suite, Google Suite, etc.)
  • Demonstrate excellent oral and written communication skills.
  • Excellent organizational skills and strong problem-solving skills.
  • Ability to prioritize and handle multiple tasks independently.
  • Exceptional customer service experience and skills.

EEO/AA Statement: Robertson Ryan provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state, or local laws.

This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.

Attention to all Recruiting Agencies: Recruitment at RRI works on a direct sourcing model. We will contact agencies directly if needed. RRI is not responsible for any related fees for resumes submitted to job postings, our employees or any other part of our company.

Salary.com Estimation for Trainee - Customer Service Representative (Hartford, WI) in Hartford, WI
$44,121 to $51,362
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