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Remote Insurance Underwriter Trainee Jobs in Chicago, IL

Remote roles will also have the opportunity to come together in our offices for moments that matter ... insurance, retirement savings plan, paid leave programs, paid holidays and paid time off (PTO)

Remote roles will also have the opportunity to come together in our offices for moments that matter ... In addition, Huntington provides a variety of benefits to colleagues, including health insurance ...

New

Remote roles will also have the opportunity to come together in our offices for moments that matter ... insurance, retirement savings plan, paid leave programs, paid holidays and paid time off (PTO)

Remote roles will also have the opportunity to come together in our offices for moments that matter ... In addition, Huntington provides a variety of benefits to colleagues, including health insurance ...

New

Sr Underwriting Specialist, Technology

Chicago, IL ยท On-site +1

$101K - $120K/yr

This is a full-time, exempt position with flexibility to work in a hybrid or fully remote ... Apply technical, sales and analytical skills to provide insurance solutions that help Hanover ...

Sr Underwriting Specialist, Technology

Chicago, IL ยท On-site +1

$101K - $120K/yr

This is a full-time, exempt position with flexibility to work in a hybrid or fully remote ... Apply technical, sales and analytical skills to provide insurance solutions that help Hanover ...

... auto insurers in the United States. When you join our company, we want you to feel valued ... This is not a remote role; you will be required to work in the territory listed on the job posting.

... auto insurers in the United States. When you join our company, we want you to feel valued ... This is not a remote role; you will be required to work in the territory listed on the job posting.

... auto insurers in the United States. When you join our company, we want you to feel valued ... This is not a remote role; you will be required to work in the territory listed on the job posting.

Showing results 21-40

Remote Insurance Underwriter Trainee information

See Chicago, IL salary details

$33.5K

$81.3K

$143.7K

How much do remote insurance underwriter trainee jobs pay per year?

As of Aug 21, 2026, the average yearly pay for remote insurance underwriter trainee 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 the difference between Remote Insurance Underwriter Trainee vs Remote Insurance Underwriter?

AspectRemote Insurance Underwriter TraineeRemote Insurance Underwriter
Required CredentialsTypically a bachelor's degree; some certifications beneficialRelevant certifications (e.g., CPCU, AIC) often required or preferred
Work EnvironmentTraining phase, supervised, entry-levelFull responsibilities, independent decision-making
Job ResponsibilitiesLearning underwriting processes, assisting with risk assessmentAssessing risks, approving policies, managing complex cases

The Remote Insurance Underwriter Trainee is an entry-level role focused on learning and supporting underwriting tasks, often requiring minimal experience. In contrast, the Remote Insurance Underwriter handles full underwriting responsibilities, making independent decisions. The trainee position is ideal for those starting their career, while the underwriter role is suited for experienced professionals with relevant certifications.

Can you work remotely as a remote insurance underwriter trainee?

Remote insurance underwriter trainees can often work from home, depending on the company's policies and the role's requirements. The position typically involves using underwriting software and communicating with clients or agents remotely, making remote work feasible if the necessary technology and internet connection are available.

How to get a job as a remote insurance underwriter trainee with no experience?

To become a remote insurance underwriter trainee with no experience, candidates should focus on gaining relevant knowledge through online courses in insurance principles and risk assessment, and develop strong analytical and communication skills. Entry-level positions often require a high school diploma or equivalent, and some companies may provide on-the-job training or mentorship programs for new trainees. Building familiarity with underwriting software and obtaining industry certifications can also improve chances of securing a trainee role.

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

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

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

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

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

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

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

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

Infographic showing various Remote Insurance Underwriter Trainee job openings in Chicago, IL as of July 2026, with employment types broken down into 1% As Needed, 73% Full Time, 21% Part Time, and 5% Contract. Highlights an 89% Physical, 2% Hybrid, and 9% Remote job distribution, with an average salary of $81,256 per year, or $39.1 per hour.

Title Insurance | Commercial Underwriting Talent | Remote

Godot Consulting Group

Chicago, IL โ€ข Remote

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 17 days ago


Job description

Join a high‑caliber team supporting complex commercial real estate transactions

Are you an experienced Commercial Underwriting Counsel/Underwriter who thrives on solving problems, analyzing risk, and supporting high‑value transactions? Godot currently has multiple roles open for experienced National Commercial Underwriting talent in Texas, Pennsylvania, New York, Washington D.C., Indianapolis and Chicago. Excellent pay and benefits. If you are looking to upgrade your career trajectory, contact us today. All inquiries are strictly confidential.

What You’ll Do

  • Review and analyze commercial title searches, surveys, and due‑diligence materials
  • Identify and resolve title issues, exceptions, and underwriting risks
  • Draft and approve title commitments, endorsements, and final policies
  • Collaborate with escrow, production, attorneys, and national underwriters
  • Provide guidance on complex deal structures, entity documentation, and closing requirements
  • Communicate underwriting decisions clearly to internal teams and clients
  • Ensure compliance with state regulations and underwriter guidelines

What We’re Looking For

  • 3+ years of commercial title underwriting experience (national or regional level)
  • Strong understanding of commercial real estate transactions, ALTA forms, and endorsements
  • Ability to interpret surveys, legal descriptions, easements, liens, and entity documents
  • Excellent judgment, analytical skills, and attention to detail
  • Strong communication skills and the ability to support high‑volume, fast‑moving deals
  • Experience with platforms like SoftPro, RamQuest, ResWare, or similar systems is a plus
  • A collaborative mindset and commitment to accuracy and service

What We Offer

  • Competitive compensation and performance incentives
  • Comprehensive benefits package
  • Opportunities for advancement within commercial underwriting or leadership
  • A supportive, knowledgeable team with strong industry relationships
  • Exposure to high‑profile, complex commercial transactions

Ready to Elevate Your Career?

If you’re a commercial underwriting professional who enjoys solving complex title challenges and supporting major real estate deals, we’d love to connect.

Apply today and bring your expertise to a team that values precision, partnership, and growth.

If this opportunity matches your background or if you're interested about other roles we currently recruiting for, you're welcome to apply or connect with Godot directly on LinkedIn.

Benefits

  • Health Care Plan (Medical, Dental & Vision)
  • Retirement Plan (401k, IRA)
  • Life Insurance (Basic, Voluntary & AD&D)
  • Paid Time Off (Vacation, Sick & Public Holidays)
  • Family Leave (Maternity, Paternity)
  • Work From Home