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Remote Insurance Underwriter Trainee Jobs in Madison, IL

Symmetry

Entry Level Remote Sales

Kirkwood, MO · Remote

$100K/yr

We are looking to train people to become a manager of Remote Insurance Sales Representatives and ... Following up with insurance carriers to facilitate client applications through underwriting.

Symmetry

Entry Level Remote Sales

Kirkwood, MO · On-site +1

$100K/yr

We are looking to train people to become a manager of Remote Insurance Sales Representatives and ... Following up with insurance carriers to facilitate client applications through underwriting.

InsuraTec

Sales Representative (Remote)

Godfrey, IL · Remote

... insurance license and sharpen sales skills. * Underwriting Collaboration : Work closely with ... Remote Flexibility : Enjoy the freedom to work from home on your schedule. * Work-Life Balance

InsuraTec

Sales Representative (Remote)

Clayton, MO · Remote

... insurance license and sharpen sales skills. * Underwriting Collaboration : Work closely with ... Remote Flexibility : Enjoy the freedom to work from home on your schedule. * Work-Life Balance

InsuraTec

Sales Representative (Remote)

Oakville, MO · Remote

... insurance license and sharpen sales skills. * Underwriting Collaboration : Work closely with ... Remote Flexibility : Enjoy the freedom to work from home on your schedule. * Work-Life Balance

InsuraTec

Sales Representative (Remote)

Ferguson, MO · Remote

... insurance license and sharpen sales skills. * Underwriting Collaboration : Work closely with ... Remote Flexibility : Enjoy the freedom to work from home on your schedule. * Work-Life Balance

InsuraTec

Sales Representative (Remote)

Overland, MO · Remote

... insurance license and sharpen sales skills. * Underwriting Collaboration : Work closely with ... Remote Flexibility : Enjoy the freedom to work from home on your schedule. * Work-Life Balance

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All JobsInsurance Underwriter JobsRemote Insurance Underwriter Trainee JobsRemote Insurance Underwriter Trainee Jobs in Madison, IL

Remote Insurance Underwriter Trainee information

See Madison, IL salary details

$31K

$75.1K

$132.9K

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

As of Aug 20, 2026, the average yearly pay for remote insurance underwriter trainee in Madison, IL is $75,144.00, according to ZipRecruiter salary data. Most workers in this role earn between $58,100.00 and $82,900.00 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 cities near Madison, IL are hiring for Remote Insurance Underwriter Trainee jobs?

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

Remote Insurance Underwriter Trainee jobs near you
Infographic showing various Remote Insurance Underwriter Trainee job openings in Madison, IL as of June 2026, with employment types broken down into 81% Full Time, 14% Temporary, and 5% Contract. Highlights an 42% Physical, 2% Hybrid, and 56% Remote job distribution, with an average salary of $75,144 per year, or $36.1 per hour.

Senior E&S Commercial Casualty Underwriter | Remote

KING'S INSURANCE STAFFING LLC

Saint Louis, MO • Remote

$110K - $140K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

This job post has expired today. Applications are no longer accepted.

Job description

Our client, a nationally recognized P&C Insurance Leader, is seeking to bring on an experienced Senior E&S Commercial Casualty Underwriter as part of its continued growth through the Midwest region. This role is responsible for managing a portfolio of Commercial Casualty business, including both new opportunities and renewal accounts, within the Excess & Surplus (E&S) segment. The individual will work in close partnership with distribution partners to expand business volume, maintain account retention, and ensure strong underwriting performance throughout the St. Louis market. This is a fully remote position.
Key Responsibilities
  • Independently evaluate and structure E&S casualty submissions, establishing appropriate pricing, terms, and coverage based on risk characteristics.
  • Examine financials, loss history, and exposure details to determine risk quality and alignment with underwriting guidelines.
  • Build and sustain productive relationships with brokers and agency partners to drive consistent deal flow.
  • Support the retention of existing accounts while actively pursuing new production opportunities.
  • Manage a designated territory with a focus on achieving premium growth and maintaining favorable loss experience.
  • Track marketplace shifts and emerging trends to identify areas for strategic business development.
Requirements
  • At least 3+ years of underwriting experience within commercial casualty lines, preferably in the E&S marketplace.
  • Experience in a role with production responsibilities or broker-facing territory management.
  • Strong critical thinking skills with the ability to assess risk and make sound underwriting decisions.
  • Effective communicator with a relationship-focused approach to working with external partners.
  • Undergraduate degree preferred.
Compensation/Benefits
  • Salary range of $125,000 - $150,000+ (depending on experience) including lucrative bonus potential up to 25%.
  • Company vehicle included as part of the compensation package.
  • Remote work setup with flexible scheduling options.
  • Comprehensive benefits including health, dental, vision, and life insurance.
  • Retirement savings plan with employer match.
  • Generous paid leave program.