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Remote Disability Underwriter Jobs in Chicago, IL

Ledgebrook

Cyber Underwriter

Chicago, IL · On-site +1

$75K - $135K/yr

Full remote flexibility and asynchronous work culture * Unlimited PTO and fully paid sick leave ... If you need a reasonable accommodation or alternative review process because of a disability or ...

Acrisure

Stop Loss Underwriter

Chicago, IL · On-site +1

$65K - $85K/yr

Remote (United States) About Acrisure A global fintech leader, Acrisure empowers millions of ... Comprehensive medical insurance, dental insurance, and vision insurance; life and disability ...

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 ... Comprehensive medical insurance, dental insurance, and vision insurance; life and disability ...

Berkley

Sr. Production Underwriting (Remote)

Chicago, IL · On-site +1

$85K - $125K/yr

Complete underwriting checklists outlining underwriting thought process, loss analysis, pricing ... Base Salary Range: $85k-$125k Benefits include Health, dental, vision, dental, life, disability ...

Berkley

Sr. Production Underwriting (Remote)

Chicago, IL · On-site +1

$85K - $125K/yr

Complete underwriting checklists outlining underwriting thought process, loss analysis, pricing ... disability, wellness, paid time off, 401(k) and profit-sharing plans The actual salary for this ...

Berkley

Sr. Production Underwriting (Remote)

Chicago, IL · On-site +1

$85K - $125K/yr

Complete underwriting checklists outlining underwriting thought process, loss analysis, pricing ... Base Salary Range: $85k-$125k Benefits include Health, dental, vision, dental, life, disability ...

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All JobsDisability Underwriter JobsRemote Disability Underwriter JobsRemote Disability Underwriter Jobs in Chicago, IL

Remote Disability Underwriter information

See Chicago, IL salary details

$33.5K

$81.3K

$143.7K

How much do remote disability underwriter jobs pay per year?

As of Sep 8, 2026, the average yearly pay for remote disability underwriter in Chicago, IL is $81,256.00, according to ZipRecruiter salary data. Most workers in this role earn between $62,800.00 and $89,600.00 per year, depending on experience, location, and employer.

What is a remote disability underwriter?

A Remote Disability Underwriter is an insurance professional who evaluates and assesses disability insurance applications while working from a remote location. Their primary role is to determine the risk of insuring an applicant by reviewing medical records, employment details, and other relevant information. They use this information to decide whether to approve, modify, or decline disability insurance coverage and to set appropriate premiums. Working remotely allows them to perform these duties from home or another off-site location, often using secure online systems.

What skills and qualifications are needed to be a remote disability underwriter?

To thrive as a Remote Disability Underwriter, you need strong analytical skills, thorough knowledge of insurance principles, and experience with disability underwriting, often supported by a relevant bachelor's degree or industry certifications such as FLMI or ALHC. Familiarity with underwriting software, insurance databases, and secure digital communication platforms is typically required. Exceptional attention to detail, independent decision-making, and effective written communication are vital soft skills for this remote role. These competencies ensure accurate risk assessment, regulatory compliance, and clear collaboration with clients and colleagues in a virtual environment.

What challenges do remote disability underwriters face and how can they manage them?

Remote disability underwriters often encounter challenges such as limited direct communication with colleagues, navigating complex case files independently, and managing time efficiently across multiple cases. To address these, it's important to leverage digital collaboration tools, proactively schedule check-ins with team members, and stay organized with robust task-management systems. Additionally, maintaining clear communication with claims adjusters and medical professionals helps ensure accurate risk assessments and efficient workflow.

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

AspectRemote Disability UnderwriterRemote Claims Adjuster
Required CredentialsInsurance license, underwriting certificationsClaims handling certifications, insurance licenses
Work EnvironmentHome-based, insurance company settingHome-based, insurance or claims company
Industry UsagePrimarily in life, health, disability insuranceIn property, casualty, health insurance claims
Job FocusAssessing risk, approving disability insurance policiesInvestigating, evaluating, and settling claims

Remote Disability Underwriters and Remote Claims Adjusters both work in the insurance industry from home, but their roles differ. Underwriters focus on evaluating applications and approving policies, while Claims Adjusters handle claims processing and investigations. Both roles require industry-specific certifications and are essential in the insurance process, but they serve different functions within the insurance lifecycle.

What are the most commonly searched types of Disability Underwriter jobs in Chicago, IL?

The most popular types of Disability Underwriter jobs in Chicago, IL are:

What are popular job titles related to Remote Disability Underwriter jobs in Chicago, IL?

For Remote Disability Underwriter jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Remote Disability Underwriter jobs in Chicago, IL look for?

The top searched job categories for Remote Disability Underwriter jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Remote Disability Underwriter jobs?

Cities near Chicago, IL with the most Remote Disability Underwriter job openings:

Remote Disability Underwriter jobs near you
Infographic showing various Remote Disability Underwriter job openings in Chicago, IL as of September 2026, with employment types broken down into 100% Full Time. Highlights an 100% Remote job distribution, with an average salary of $81,256 per year, or $39.1 per hour.

Cyber Underwriter

Ledgebrook

Chicago, IL • On-site, Remote

$75K - $135K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted yesterday

Job description

Description
Does it ever feel like you're underwriting with one hand tied behind your back? Tired of the struggles and inefficiencies associated with legacy systems and processes? Spending too much of your time and energy navigating corporate politics? All leaving your efforts to innovate and deliver underwriting excellence languishing?
At Ledgebrook, we believe a career in underwriting can be so much more. You bring the passion and entrepreneurial spirit; we'll provide the platform to unleash the very best of your talents and skills. Together, we'll celebrate and reward success! Are you intrigued? Then read on and apply now to advance your career at Ledgebrook.
About the Role
We are seeking experienced Cyber, Tech and MPL underwriting talent to join our growing team whose mission is focused on building a profitable book of specialty lines business. Our vision is to deliver market relevant solutions to our key wholesale trading partners in a more frictionless environment that places an emphasis on efficiencies and quality to meet or exceed our broker's overall needs in a risk differentiated manner. If you possess an entrepreneurial passion that includes a proven track history of delivering underwriting excellence and are seeking an opportunity to break out of the traditional insurance company mould, we're looking for you!
As a member of the Specialty Lines team, you will regularly interact with our wholesale trading partners over the phone, virtually and in-person to drive submission flow and convert on the best opportunities quoted. We are looking for disciplined underwriting candidates that possess a strong overall cyber liability background with experience underwriting risks of all industries and sizes.
About you
We love working with people who are eager to learn constantly and genuinely excited about the chaotic, rewarding process of building a company from the ground up.
You'll be a great fit if you bring:
  • A Strong Moral Compass: You believe in doing the right thing, period. We have a strict zero-tolerance policy for toxic behaviors
  • Customer-First Empathy: You are passionate about delivering an exceptional experience to everyone you work with, both inside and outside the company
  • Intellectual Curiosity: You naturally question the status quo and love finding innovative ways to solve problems
  • A Growth Mindset: You possess a hunger for continuous learning and want to constantly expand your skillset
  • Urgency & Prioritization: You can pivot quickly and balance the need to get things right with the speed of getting them done right now
  • A Solution-Oriented Outlook: When things go wrong, you don't look for blame-you immediately focus on how to fix it
  • Transparent Communication: You value honesty, clarity, and open feedback
  • Team-First Energy: You want to win together as a high-performing team and actively build connections across our remote locations

Requirements
As a future Cyber Liability Underwriter, your experience and qualifications must include:
  • 2+ years experience as a cyber, tech and/or MPL underwriter
  • Experience working in the E&S market
  • Ability to work as a team player or independently in a fast-paced work environment
  • Deep wholesale broker trading relationships
  • Effective communication skills to articulate our appetite and develop wholesale broker relationships
  • Understanding of pricing and risk selection criteria to achieve underwriting profit
  • Advanced understanding of data analysis and execution of portfolio management objectives
  • Intellectual curiosity, problem solving skills, and a sense of urgency
  • Responsive, customer service focused mindset and behaviors
  • Ability to make timely decisions with appropriate information and consultation
  • A strong entrepreneurial drive and desire to build and win together as a high performing team
  • Ability to travel to meet with assigned brokers or with the broader team to participate in industry conference or events

While the preference is for this person to sit in the Chicago or surrounding area, we are a fully remote company and will consider other US based applications.
Benefits
  • Full remote flexibility and asynchronous work culture
  • Unlimited PTO and fully paid sick leave
  • Comprehensive health benefits, including medical, dental, and vision coverage, plus HSA and FSA options
  • Additional financial protection and retirement benefits, including a 401(k), company-paid life insurance, and disability coverage
  • A high degree of ownership, autonomy, and the opportunity to help build and shape a growing company
  • The chance to make a meaningful impact while working alongside an ambitious, high-performing team
  • Exposure to the challenges and opportunities of a fast-growing startup environment

Compensation
  • Base Salary Range $75,000-135,000 This is a good-faith compensation range based on what Ledgebrook reasonably expects to pay for this position at the time of this posting. Actual compensation may vary based on a variety of relevant factors including experience, qualifications, geographic location and other relevant factors.
  • Employees in this position are eligible to participate in Ledgebrook's equity incentive program.

For Candidates Applying From The U.S.:
Please note: This position is open only to candidates who are authorized to work in the United States without the need for current or future employer-sponsored work authorization. We are unable to offer sponsorship at this time.
Ledgebrook may use Artificial Intelligence ("AI") as part of the job application process, including to assist us in evaluating your application. AI is used as a support tool, and hiring decisions are made by human recruiters. By submitting your information, you acknowledge that the company may use AI tools as part of our evaluation. If you need a reasonable accommodation or alternative review process because of a disability or other legally protected basis, contact hiring@ledgebrook.com. Requesting an accommodation will not negatively affect your application.

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