2

Remote Stop Loss Insurance Jobs in Wisconsin (NOW HIRING)

... Insurance Group (CSAA IG), a AAA insurer, is one of the leading personal lines property and ... Your Work: * Manage homeowners property claims from first notice of loss through resolution ...

Desk Auto Claims Adjuster

Madison, WI · On-site +1

$49K - $65K/yr

You'll enjoy the flexibility of remote work while serving customers across Wisconsin. Candidates ... loss claims. • Bachelor's degree in Business Administration, Risk Management & Insurance, or a ...

Showing results 21-40

Remote Stop Loss Insurance information

What is remote stop loss insurance?

Remote stop loss insurance is a type of coverage designed to protect self-funded employers from large or catastrophic claims, but managed and administered through digital or remote platforms. This insurance reimburses employers for claims that exceed a predetermined limit, helping them manage risk and avoid significant financial loss. The 'remote' aspect refers to the use of online tools and services for policy management, claims processing, and communication, allowing for flexible and efficient administration without the need for in-person meetings. This is particularly beneficial for companies with distributed teams or those seeking streamlined, technology-driven solutions.

What are some common challenges faced by professionals working in remote stop loss insurance roles?

One common challenge in remote stop loss insurance roles is maintaining clear and effective communication with underwriters, brokers, and clients, since much of the collaboration happens virtually. Additionally, staying updated on changing regulations and market trends requires proactive self-learning and digital resourcefulness. Managing sensitive data securely and ensuring timely turnaround on complex claims or policy analysis can also be demanding when working remotely. Building strong relationships with team members and clients, despite the lack of in-person interaction, is key to long-term success in this field.

What are the key skills and qualifications needed to thrive as a remote stop loss insurance specialist, and why are they important?

To excel as a Remote Stop Loss Insurance Specialist, you need expertise in health insurance underwriting, risk assessment, and policy analysis, often supported by a background in insurance or finance. Familiarity with industry-standard claims management systems, CRM platforms, and regulatory compliance tools is essential. Strong analytical thinking, attention to detail, and effective written communication are crucial soft skills for success in a remote environment. These abilities ensure accurate risk evaluation, regulatory adherence, and clear client interactions, which are critical for managing high-value stop loss insurance contracts.

What is the difference between Remote Stop Loss Insurance vs Remote Underwriter?

AspectRemote Stop Loss InsuranceRemote Underwriter
CredentialsInsurance licenses, actuarial knowledgeInsurance licenses, underwriting certifications
Work EnvironmentInsurance companies, brokers, remoteInsurance companies, remote or office
Industry UsageHealth and self-funded plansInsurance policy assessment and risk evaluation

Remote Stop Loss Insurance professionals focus on providing coverage for self-funded health plans, managing risk, and setting policy terms. Remote Underwriters evaluate insurance applications, assess risks, and determine policy eligibility. While both roles require insurance knowledge and licenses, Stop Loss Insurance specialists concentrate on risk management for health plans, whereas Underwriters focus on evaluating individual applications. Understanding these differences helps clarify career paths and job expectations in the insurance industry.

What are popular job titles related to Remote Stop Loss Insurance jobs in Wisconsin?

For Remote Stop Loss Insurance jobs in Wisconsin, the most frequently searched job titles are:

What cities in Wisconsin are hiring for Remote Stop Loss Insurance jobs?

Cities in Wisconsin with the most Remote Stop Loss Insurance job openings:

Infographic showing various Remote Stop Loss Insurance job openings in Wisconsin as of August 2026, with employment types broken down into 100% Full Time. Highlights an 100% Remote job distribution.

Sr. Examiner, Homeowner Claims Multi-State - Remote

CSAA

Remote

Full-time

Retirement

Re-posted 4 hours ago


Job description

External candidates: In order for your application to be correctly processed please sign-in before you apply

Internal candidates: Please go to Workday and click "Find Jobs" link under Career

Thank you for considering opportunities with us!

Job Title

Sr. Examiner, Homeowner Claims Multi-State - Remote

Requisition Number

R7899 Sr. Examiner, Homeowner Claims Multi-State - Remote (Open)

Location

Colorado - Home Teleworkers

Additional Locations

Alabama - Home Teleworkers, Alabama - Home Teleworkers, Arizona - Home Teleworkers, Arkansas - Home Teleworkers, California - Home Teleworkers, Connecticut - Home Teleworkers, Delaware - Home Teleworker, District of Columbia - Home Teleworkers, Florida - Home Teleworkers, Georgia - Home Teleworkers, Idaho - Home Teleworkers, Illinois - Home Teleworkers, Indiana - Home Teleworkers, Iowa - Home Teleworkers, Kansas - Home Teleworker, Kentucky - Home Teleworkers, Louisiana - Home Teleworkers, Maine Home Teleworkers, Maryland - Home Teleworkers, Massachusetts - Home Teleworkers, Michigan - Home Teleworkers, Minnesota - Home Teleworkers, Mississippi - Home Teleworker, Missouri - Home Teleworker, Montana - Home Teleworkers {+ 21 more}

Job Information

CSAA Insurance Group (CSAA IG), a AAA insurer, is one of the leading personal lines property and casualty insurance groups in the United States. Here, every employee shapes our mission. We build innovative, human-centered solutions that help AAA members prevent, prepare for, and recover from life's uncertainties. You will join a collaborative, inclusive culture where your strengths have room to grow and your ideas can drive real impact. Step into a role where you can contribute to our shared success through meaningful work.

We are actively hiring for a Sr. Examiner, Homeowner Claims Multi-State - Remote

Your Role: Under close supervision, investigates, evaluates, negotiates, and settles homeowners property and personal property claims from first notice of loss through resolution. Serves as the owning adjuster for all assigned claims, including low- to higher-complexity losses that may require oversight of service providers conducting physical or virtual inspections. May assign, coordinate, and oversee independent adjuster assignments. This developmental role is designed to build the knowledge and skills necessary to progress to the competency level of a Level 5 Homeowner Adjuster.

Your Work:

  • Manage homeowners property claims from first notice of loss through resolution, handling low- to high-complexity losses.
  • Investigate coverage by analyzing policy language, endorsements, and applicable state regulations; communicate coverage decisions and resolve coverage-related questions.
  • Coordinate emergency mitigation services to protect property from further damage while delivering a positive customer experience.
  • Write and review repair estimates, evaluate contractor estimates, and determine appropriate claim payments and reserves.
  • Handle all applicable first-party coverages and Key Operating Losses (KOLs), escalating more complex claims when appropriate.
  • Identify subrogation and Special Investigation Unit (SIU) opportunities and prepare referrals as needed.
  • Manage relationships with independent adjusters (IAs), public adjusters (PAs), attorneys, contractors, and other external partners throughout the claim lifecycle.
  • Conduct virtual claim inspections and collaborate remotely with customers, vendors, and independent adjusters to evaluate damages.
  • Prepare clear, timely claim correspondence, including settlement letters, partial denials, and denials.
  • Maintain accurate claim documentation and ensure timely, compliant claim handling in accordance with company policies and regulatory requirements.

Required Experience, Education and Skills:

  • High school diploma or equivalent required.
  • Six years of related professional experience with transferable skills or four years of claims experience, preferably in homeowners claims.
  • A related bachelor's degree or higher may substitute for up to two years of required experience.
  • Ability to obtain and maintain Department of Insurance (DOI) adjuster licenses in applicable states.
  • Knowledge of homeowners insurance policies, coverage, and claims handling procedures.
  • Knowledge of the Xactimate estimating platform.
  • Excellent verbal and written communication skills, including the ability to explain complex coverage decisions and prepare customer correspondence.

What would make us excited about you:

  • Bachelor's degree.
  • Two years of experience handling complex property claims.
  • Knowledge of residential home construction and repair practices.

Please note we are hiring for this role remote anywhere in the United States with the following exceptions: Hawaii and Alaska.

Why Choose a Career at CSAA IG?

At CSAA IG, we are a mission-driven organization proudly committed to empowering our members, our employees, and our communities to thrive.

Recognition: We offer a total compensation package, annual bonus eligibility for most roles, 401(k) with a company match, and so much more! Read more about what we offer and what it is like to be a part of our dynamic team at https://careers.csaainsurance.aaa.com/us/en/benefits.

Career Growth: We believe in growth for everyone. Here at CSAA IG, leaders and mentors partner with employees to align interests, unlock development opportunities, and support longterm success.

Flexible Workplace: We embrace a remote-first culture through our Flexible Workplace. Most employees hold Home-Flex roles, working primarily from home, often with the flexibility to work from various locations including CSAA offices. Our flexible workplace empowers you to balance remote work with intentional inperson moments that deepen connection and collaboration.

Inclusion and Belonging: An inclusive and welcoming workplace is the cornerstone of our success. By fostering an environment where people feel valued and heard, we deepen our ability to understand and meet the unique needs of our members. This strengthens innovation and enhances our products and services, giving us a competitive edge in the market.

Sustainability: As climate change leads to more frequent and severe weather events, we are taking bold action to build more resilient communities and reduce our environmental impact. Submit your application to be considered. We communicate via email, so check your inbox and/or your spam folder to ensure you don't miss important updates from us.

CSAA is committed to providing reasonable accommodations to qualified applicants and employees with disabilities or other limitations. If you would like to request an accommodation to participate in the job application or interview process, please contact TalentAcquistion@csaa.com

If you apply and are selected to continue in the recruiting process, we will schedule a preliminary call with you to discuss the role and will disclose during that call the available salary/hourly rate range based on your location. Factors used to determine the actual salary offered may include location, experience, or education.

CSAA does not provide visa sponsorship for this role. Applicants must have authorization to work indefinitely in the US. Please do not apply for this role if at any time (now or in the future) you will need immigration support (i.e., H-1B, TN, STEM OPT Training Plans, etc.).

CSAA Insurance Group is an equal opportunity employer.

#LI-CH1

.

The national average hourly rate for this position is $37.26-$41.40. However, we have a location-based compensation structure. Our salary ranges vary and are calculated based on work location. The starting pay range for this position across all the states we hire in is $37.26-$49.72. This role also includes an opportunity for a company-wide annual discretionary bonus, through our Annual Incentive Plan (AIP), of up to 10% of eligible pay.This job posting will be unposted on Wed, 2 Sep 2026.