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Director Insurance Jobs in Wisconsin (NOW HIRING)

First Weber Realtors

Insurance Producer

Brookfield, WI · On-site

Perform responsibilities as directed achieving desired results within expected time frames and with ... Working knowledge of insurance agency operations, coverages, rates, markets and applicable ...

First Weber Realtors

Insurance Producer

Brookfield, WI · On-site

Perform responsibilities as directed achieving desired results within expected time frames and with ... Working knowledge of insurance agency operations, coverages, rates, markets and applicable ...

The Juris Agency

Insurance Agent Apprentice

Milwaukee, WI · On-site

$36K - $100K/yr

Throughout the program, you'll receive direct mentorship from highly successful and experienced Farmers Insurance professionals who have built outstanding careers and understand what it takes to ...

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All JobsInsurance JobsDirector Insurance JobsDirector Insurance Jobs in Wisconsin

Director Insurance information

See Wisconsin salary details

$19.2K

$96.2K

$200K

How much do director insurance jobs pay per year?

As of Sep 15, 2026, the average yearly pay for director insurance in Wisconsin is $96,182.00, according to ZipRecruiter salary data. Most workers in this role earn between $55,701.00 and $126,012.00 per year, depending on experience, location, and employer.

What does a director insurance do?

A Director of Insurance is responsible for overseeing an organization's insurance programs and risk management strategies. They ensure that the company has adequate coverage for various risks, negotiate with insurers, and develop policies to minimize potential losses. Additionally, they may manage a team, stay updated on industry regulations, and analyze data to make informed decisions about coverage and claims. Their goal is to protect the organization’s assets while optimizing insurance costs.

What are the key skills and qualifications needed to thrive as a director insurance, and why are they important?

To thrive as a Director of Insurance, you need in-depth knowledge of insurance products, risk management, regulatory compliance, and leadership experience, often backed by a bachelor’s or master’s degree in finance, business, or a related field. Familiarity with industry-standard insurance management software, data analytics platforms, and relevant certifications such as CPCU or ARM is essential. Strong strategic thinking, negotiation, and team leadership skills set exceptional candidates apart. These skills and qualifications are vital for driving organizational growth, ensuring regulatory adherence, and leading high-performing teams in a complex and evolving industry.

What are some common challenges faced by a director insurance when leading cross-functional teams?

A Director of Insurance often leads teams that include underwriting, claims, compliance, and sales professionals, requiring strong coordination and communication skills. Common challenges include balancing differing departmental priorities, aligning on regulatory requirements, and ensuring seamless customer experiences. Successfully managing these dynamics involves fostering collaboration, setting clear objectives, and staying updated on industry trends. Directors also need to adapt quickly to regulatory changes and technological advancements that impact workflow and client needs.

What is the difference between Director Insurance vs Insurance Manager?

AspectDirector InsuranceInsurance Manager
CredentialsTypically requires a bachelor’s degree in insurance, business, or related field; professional certifications like CPCU or ARM are commonUsually holds similar degrees and certifications, such as CPCU or ARM, but may have less seniority
Work EnvironmentOversees multiple teams or departments, strategic planning, and high-level decision-making within insurance companiesManages daily operations of insurance teams, handles policy administration, and ensures compliance
Employer & Industry UsageFound in large insurance firms, corporations, and brokerage firms, focusing on strategic leadershipCommon in insurance companies, agencies, and departments, focusing on operational management

The main difference between a Director Insurance and an Insurance Manager lies in their scope and level of responsibility. Directors typically focus on strategic planning and leadership at a higher level, while Managers handle day-to-day operations and team management. Both roles require relevant credentials and industry experience, but Directors usually have broader oversight and influence within the organization.

What are the most commonly searched types of Insurance jobs in Wisconsin?

The most popular types of Insurance jobs in Wisconsin are:

What are popular job titles related to Director Insurance jobs in Wisconsin?

For Director Insurance jobs in Wisconsin, the most frequently searched job titles are:

What job categories do people searching Director Insurance jobs in Wisconsin look for?

The top searched job categories for Director Insurance jobs in Wisconsin are:

What cities in Wisconsin are hiring for Director Insurance jobs?

Cities in Wisconsin with the most Director Insurance job openings:

Infographic showing various Director Insurance job openings in Wisconsin as of September 2026, with employment types broken down into 100% Full Time. Highlights an 100% In-person job distribution, with an average salary of $96,182 per year, or $46.2 per hour.

Trainee - Customer Service Representative (Shawano, WI)

Shawano, WI • On-site

Robertson Ryan Insurance
Insurance Services • 201 - 500 employees
Learn more about Robertson Ryan Insuranceexternal

$15 - $20.50/hr

Full-time

Re-posted 22 days ago

Robertson Ryan Insurance rating

8.7

Company rating: 8.7 out of 10

Based on 7 frontline employees who took The Breakroom Quiz

Job description

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 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 Shawano, WI office 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):

  • 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-time in office at our Shawano, 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.
Interested in the position? Apply now or email mstielow@robertsonryan.com!

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.

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