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Remote Insurance Underwriter Jobs in Chicago, IL

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 ...

The Hartford

AVP Applied AI

Chicago, IL · On-site +1

... Business Insurance. This role partners closely with underwriting, product, actuarial, and ... This role can have a Hybrid or Remote work schedule. Candidates who live near one of our office ...

Honeycomb Insurance

Senior Underwriter, Midwest

Chicago, IL · On-site +1

$101K - $120K/yr

  • Medical

  • Retirement

  • PTO

Maintain familiarity and compliance with state insurance regulations and ISO rules for all states ... This position is remote in the Midwest or Hybrid out of our Chicago Office, 3X weekly Benefits

Ledgebrook

Cyber Underwriter

Chicago, IL · On-site +1

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

... insurance company mould, we're looking for you! As a member of the Specialty Lines team, you will ... An eagerness to actively participate and connect with the whole team, across remote locations * An ...

Berkley

Executive Technology Underwriter

Naperville, IL · On-site +1

$120K - $150K/yr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Berkley Technology Underwriters is a global insurance provider offering property, casualty ... remote work arrangements may be considered. Candidates must be willing and able to travel ...

New

Anderson Johnson Agency

Remote Insurance Agent

Joliet, IL · Remote

$60K - $120K/yr

... insurance agents who are professional, coachable, self-motivated, and interested in building long-term success in a supportive, values-based environment. This is a remote, commission-based ...

Hyperiongrp

Associate Underwriter Earthquake

Chicago, IL · On-site +1

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

Hybrid or Remote. Role overview DUAL North America is seeking an Associate Underwriter for the ... Foundational knowledge of insurance principles * Proficiency in Microsoft Office Suite (Word, Excel ...

Howden Group

Associate Underwriter Earthquake

Chicago, IL · On-site +1

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

Hybrid or Remote. Role overview DUAL North America is seeking an Associate Underwriter for the ... Foundational knowledge of insurance principles * Proficiency in Microsoft Office Suite (Word, Excel ...

Berkley

Executive Technology Underwriter

Naperville, IL · On-site +1

$120K - $150K/yr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Company Details Berkley Technology Underwriters is a global insurance provider offering property ... remote work arrangements may be considered. Candidates must be willing and able to travel ...

Promoted2

Remote Insurance Agent

Elgin, IL · Remote

$69K/yr

  • Medical

  • Dental

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

HMG Careers

Remote Insurance Agent

East Chicago, IN · Remote

$69K/yr

  • Medical

  • Dental

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

HMG Careers

Remote Insurance Agent

Harvey, IL · Remote

$69K/yr

  • Medical

  • Dental

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

HMG Careers

Remote Insurance Agent

Waukegan, IL · Remote

$69K/yr

  • Medical

  • Dental

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

Promoted2

Remote Insurance Agent

Gary, IN · Remote

$69K/yr

  • Medical

  • Dental

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

Promoted2

Remote Insurance Agent

Naperville, IL · Remote

$69K/yr

  • Medical

  • Dental

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

Promoted2

Remote Insurance Agent

Elk Grove Village, IL · Remote

$69K/yr

  • Medical

  • Dental

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

Promoted2

Remote Insurance Agent

Chicago, IL · Remote

$69K/yr

  • Medical

  • Dental

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

Promoted2

Remote Insurance Agent

Joliet, IL · Remote

$69K/yr

  • Medical

  • Dental

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

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Showing results 1-20

All JobsInsurance Underwriter JobsRemote Insurance Underwriter JobsRemote Insurance Underwriter Jobs in Chicago, IL

Remote Insurance Underwriter information

See Chicago, IL salary details

$33.5K

$81.3K

$143.8K

How much do remote insurance underwriter jobs pay per year?

As of Aug 13, 2026, the average yearly pay for remote insurance underwriter in Chicago, IL is $81,320.00, according to ZipRecruiter salary data. Most workers in this role earn between $62,900.00 and $89,700.00 per year, depending on experience, location, and employer.

What are some common challenges faced by remote insurance underwriters and how can they be managed?

Remote insurance underwriters often face challenges such as maintaining effective communication with team members and staying updated on changing underwriting guidelines. Working remotely requires strong self-discipline to manage workloads across multiple cases and deadlines without direct in-person supervision. Utilizing collaboration tools, setting regular check-ins with colleagues, and staying proactive in seeking clarification on complex cases can help overcome these challenges. Additionally, remote underwriters should take advantage of ongoing training resources to keep their skills and industry knowledge current.

What does a remote insurance underwriter do?

The job duties of a remote insurance underwriter focus on assessing the risk in insurance policies. In this virtual position, you work from home or from a remote office to evaluate the risk of each client who has applied. You may also review insurance coverage for excessive risk. After reviewing financial documents, risk assessments, and insurance needs, your responsibilities include deciding whether to approve or deny an insurance application. Underwriting may require you to deny coverage for clients that you deem high risk.

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

To thrive as a Remote Insurance Underwriter, you need strong analytical abilities, attention to detail, and a solid understanding of risk assessment and insurance principles, typically backed by a bachelor’s degree in finance, business, or a related field. Proficiency with underwriting software, risk management systems, and familiarity with industry certifications like CPCU or AU is highly valued. Excellent written communication, time management, and decision-making skills help remote underwriters collaborate effectively and manage workloads independently. These skills ensure accurate risk evaluations, compliance with regulations, and efficient remote operations within the insurance sector.

What is a remote insurance underwriter?

A remote insurance underwriter is a professional who evaluates insurance applications, assesses risk, and determines policy terms and premiums, all while working from a location outside of a traditional office, such as from home. They review documentation, analyze data, and make recommendations using digital tools and communication platforms. This role requires strong analytical skills, attention to detail, and knowledge of insurance regulations and guidelines. Remote underwriters often collaborate with agents, brokers, and clients electronically to ensure accurate policy issuance and risk management.

What is the difference between Remote Insurance Underwriter vs Remote Insurance Claims Adjuster?

AspectRemote Insurance UnderwriterRemote Insurance Claims Adjuster
Required CredentialsInsurance licenses, underwriting certificationsClaims adjusting licenses, insurance certifications
Work EnvironmentOffice or remote, analyzing risk dataRemote, investigating claims and assessing damages
Employer & Industry UsageInsurance companies, brokers, underwritersInsurance companies, third-party claims firms

Remote Insurance Underwriters and Claims Adjusters both work in the insurance industry, often remotely, but focus on different aspects. Underwriters evaluate risk to determine policy terms, while Claims Adjusters investigate and settle claims. Both roles require specific licenses and certifications, and are essential in the insurance process, but they serve distinct functions within the industry.

More about Remote Insurance Underwriter jobs
What are the most commonly searched types of Insurance Underwriter jobs in Chicago, IL? The most popular types of Insurance Underwriter jobs in Chicago, IL are:
What are popular job titles related to Remote Insurance Underwriter jobs in Chicago, IL? For Remote Insurance Underwriter jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Remote Insurance Underwriter jobs in Chicago, IL look for? The top searched job categories for Remote Insurance Underwriter jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Remote Insurance Underwriter jobs? Cities near Chicago, IL with the most Remote Insurance Underwriter job openings:
Remote Insurance Underwriter jobs near you
Infographic showing various Remote Insurance Underwriter job openings in Chicago, IL as of August 2026, with employment types broken down into 87% Full Time, and 13% Part Time. Highlights an 100% Remote job distribution, with an average salary of $81,320 per year, or $39.1 per hour.

Underwriter

Captive Resources

Itasca, IL • On-site, Remote

Full-time

Re-posted 19 days ago

Job description

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 understanding of both medical costs and insurance principles.
EDUCATION AND EXPERIENCE: A bachelor's degree in business, finance, insurance, mathematics, or a related field. 2 -5 years of experience in insurance underwriting, preferably in the health insurance or medical stop-loss field. Experience with medical claims analysis, pricing, and risk management is essential.
SKILLS/COMPETENCIES REQUIREMENTS:
  • Stay updated on industry trends, regulatory changes, and best practices in medical stop-loss underwriting.
  • Risk management principles and stop-loss insurance products.
  • Medical terminology, healthcare costs, and trends in medical claims.
  • Regulatory and compliance issues in insurance underwriting.
  • Strong analytical and problem-solving abilities.
  • Proficiency in underwriting software (Connexure ESL Office).
  • Excellent written and verbal communication skills for client interaction and report creation.

ESSENTIAL DUTIES AND RESPONSIBILITIES:
  • Evaluate submissions for medical stop-loss insurance of assigned captive program(s), assessing the risk posed by each potential policyholder.
  • Analyze medical claims data and historical health costs to determine appropriate stop-loss coverage levels, including individual and aggregate limits.
  • Review group health plans, claims experience, and member demographics to assess the potential for high-cost claims.
  • Develop premium pricing for stop-loss insurance policies based on risk analysis and underwriting guidelines within delegate authority.
  • Establish appropriate retention levels, deductible amounts, and policy terms based on the group's needs and risk factors.
  • Analyze claims data to assess trends, predict future claims, and identify risk patterns.
  • Use various tools, including statistical analysis and software systems, to track claims history and predict future healthcare costs.
  • Collaborate with clinical risk management team to assess potential for ongoing claims liability.
  • Engage with internal and external stakeholders to explain policy terms, underwriting decisions, and negotiate terms when necessary.
  • Support the sales team by providing underwriting insights and assisting with the proposal process for new business.
  • Ensure all underwriting activities comply with regulatory requirements, industry standards, and company guidelines.
  • Maintain accurate records of underwriting decisions, policies, claims history, and communication with clients.

TRAVEL: Occasional travel may be required for meetings, conferences, or client visits. This includes compliance with all of the requirements of the localities and destinations, as well as transportation carrier requirements.
Click here to view all of our current benefits.
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