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Remote Stop Loss Insurance Jobs in Chicago, IL (NOW HIRING)

Allied Benefit Systems

Supervisor, Stop Loss

Chicago, IL · Remote

$147K/yr

At least 5 years group health insurance/benefits experience required. * At least 2 years ... Remote Here at Allied, we believe that great talent can thrive from anywhere. Our remote friendly ...

Allied

Supervisor, Stop Loss

Chicago, IL · On-site +1

$60K - $65K/yr

At least 5 years group health insurance/benefits experience required. * At least 2 years ... Remote Here at Allied, we believe that great talent can thrive from anywhere. Our remote friendly ...

Captive Resources

Underwriter

Itasca, IL · On-site +1

The Underwriter is responsible for evaluating and underwriting stop-loss insurance. The role involves analyzing medical risk, pricing policies, and making recommendations based on a thorough ...

Acrisure

Senior Stop Loss Underwriter

Chicago, IL · On-site +1

$90K - $125K/yr

Remote (United States) About Acrisure A global fintech leader, Acrisure empowers millions of ... of insurance, reinsurance, payroll, benefits, cybersecurity, mortgage services - and more. In the ...

Allied

Associate Client Executive

Chicago, IL · On-site +1

$72K - $75K/yr

Position and showcase products, rates, stop loss, and expanded product portfolios to increase sales ... Experience with Group health insurance and self-funded health plans preferred. * Excellent written ...

Allied

Client Executive

Chicago, IL · On-site +1

$130K - $135K/yr

Position's products, rates, and stop loss and expanded product portfolios to increase sales and ... Remote Here at Allied, we believe that great talent can thrive from anywhere. Our remote friendly ...

Renalogic

Client Success Manager (Remote)

Chicago, IL · Remote

$85K - $95K/yr

... stop loss carriers). You'll manage the end-to-end client experience, ensuring that new clients of ... Experience in the self-funded health insurance space, with familiarity of brokerages, TPA, and ...

Renalogic

Client Success Manager

Chicago, IL · On-site +1

$85K - $95K/yr

US; fully remote with some travel Who We Are Renalogic is dedicated to helping our clients manage ... stop loss carriers). You'll manage the end-to-end client experience, ensuring that new clients of ...

Renalogic

Client Success Manager

Chicago, IL · On-site +1

$85K - $95K/yr

US; fully remote with some travel Who We Are Renalogic is dedicated to helping our clients manage ... stop loss carriers). You'll manage the end-to-end client experience, ensuring that new clients of ...

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All JobsStop Loss Insurance JobsRemote Stop Loss Insurance JobsRemote Stop Loss Insurance Jobs in Chicago, IL

Remote Stop Loss Insurance information

See Chicago, IL salary details

$16

$32

$64

How much do remote stop loss insurance jobs pay per hour?

As of Aug 21, 2026, the average hourly pay for remote stop loss insurance in Chicago, IL is $32.37, according to ZipRecruiter salary data. Most workers in this role earn between $19.81 and $48.80 per hour, depending on experience, location, and employer.

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 the most commonly searched types of Stop Loss Insurance jobs in Chicago, IL?

The most popular types of Stop Loss Insurance jobs in Chicago, IL are:

What are popular job titles related to Remote Stop Loss Insurance jobs in Chicago, IL?

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

What job categories do people searching Remote Stop Loss Insurance jobs in Chicago, IL look for?

The top searched job categories for Remote Stop Loss Insurance jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Remote Stop Loss Insurance jobs?

Cities near Chicago, IL with the most Remote Stop Loss Insurance job openings:

Remote Stop Loss Insurance jobs near you
Infographic showing various Remote Stop Loss Insurance job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 74% Full Time, 20% Part Time, and 5% Contract. Highlights an 89% Physical, 2% Hybrid, and 9% Remote job distribution, with an average salary of $67,323 per year, or $32.4 per hour.

Supervisor, Stop Loss

Allied Benefit Systems

Chicago, IL • Remote

$147K/yr

Full-time

Medical, Dental, Vision, Life, PTO

Posted 6 days ago

Allied Benefit Systems rating

8.1

Company rating: 8.1 out of 10

Based on 5 frontline employees who took The Breakroom Quiz

108th of 495 rated business services

Job description

POSITION SUMMARY

The Supervisor, Stop Loss is responsible for assisting the Manager, Stop Loss with overseeing the department. Duties include auditing and tracking stop loss claim filings, reimbursements, and cash advance claims to ensure the department is running in an efficient and thorough manner. The Supervisor, Stop Loss also works closely with Stop Loss Data Specialist and Reimbursement Specialist on administrative, organizational, and auditing functions.

ESSENTIAL FUNCTIONS

  • Perform weekly audits of specific claims to ensure all claims were filed correctly and all reimbursements have been received.
  • Update and manage the stop loss tracking and specific logs to monitor the current status of members over the specific deductible.
  • Review and accurately record stop loss reimbursements.
  • Gather and prepare the data required to file Rx stop loss claims.
  • Responsible for the filing of aggregate claims and securing reimbursements.
  • Assist with making claim adjustments.
  • Organize the enrollment of new clients into the ACH reimbursement program.
  • Lead, coach, motivate and develop. Responsible for one on one meetings, performance appraisals, growth opportunities and attracting new talent.
  • Clearly communicate expectations, provide employees with the training, resources, and information needed to succeed.
  • Actively engage, coach, counsel and provide timely, and constructive performance feedback.
  • Other duties as assigned.

EDUCATION

  • Bachelor's degree or equivalent work experience required.

EXPERIENCE AND SKILLS

  • At least 5 years group health insurance/benefits experience required.
  • At least 2 years supervisory experience required.
  • Must be highly proficient in the use of Microsoft Word, Excel, and Outlook
  • Must have the ability to easily learn new computer applications.

POSITION COMPETENCIES

  • Accountability
  • Coaching and Feedback
  • Collaboration
  • Customer Focus
  • Decision Making
  • Execution Management
  • People Leadership

PHYSICAL DEMANDS

  • This is a standard desk role requiring extended sitting and computer work.

WORK ENVIRONMENT

  • Remote

Here at Allied, we believe that great talent can thrive from anywhere. Our remote friendly culture offers flexibility and the comfort of working from home, while also ensuring you are set up for success. To support a smooth and efficient remote work experience, the internet connection must be obtained through a cable broadband or fiber optic internet service provider with speeds of at least 100Mbps download/25Mbps upload. Reliable internet service is essential for staying connected and productive.

The company has reviewed this job description to ensure that essential functions and basic duties have been included. It is not intended to be construed as an exhaustive list of all functions, responsibilities, skills, and abilities. Additional functions and requirements may be assigned by supervisors as deemed appropriate.

Compensation is not limited to base salary. Allied values our Total Rewards, and offers a competitive Benefit Package including, but not limited to, Medical, Dental, Vision, Life and Disability Insurance, Generous Paid Time Off, Tuition Reimbursement, EAP, and a Technology Stipend.

Allied reserves the right to amend, change, alter, and revise, pay ranges and benefits offerings at any time. All applicants acknowledge that by applying to the position you understand that the specific pay range is contingent upon meeting the qualification and requirements of the role, and for the successful completion of the interview selection and process. It is at the Company's discretion to determine what pay is provided to a candidate within the range associated with the role.

What Allied Benefit Systems employees say

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