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Flexible Underwriter Trainee Jobs (NOW HIRING)

IFG Companies

Underwriting Trainee

Chicago, IL · On-site

$65K - $75K/yr

Draft POSITION SUMMARY The Underwriter Trainee ("Trainee") participates in the commercial ... flexible spending, short-term and long-term disability insurance, life insurance, paid parental ...

IFG Companies

Underwriting Trainee

Scottsdale, AZ · On-site

$65K - $75K/yr

Draft POSITION SUMMARY The Underwriter Trainee ("Trainee") participates in the commercial ... flexible spending, short-term and long-term disability insurance, life insurance, paid parental ...

IFG Companies

Underwriting Trainee

Hartford, CT · On-site

$65K - $75K/yr

Draft POSITION SUMMARY The Underwriter Trainee ("Trainee") participates in the commercial ... flexible spending, short-term and long-term disability insurance, life insurance, paid parental ...

IFG Companies

Underwriting Trainee

Alpharetta, GA · On-site

$65K - $75K/yr

Draft POSITION SUMMARY The Underwriter Trainee ("Trainee") participates in the commercial ... flexible spending, short-term and long-term disability insurance, life insurance, paid parental ...

IFG Companies

Underwriting Trainee

Chapel Hill, NC · On-site

$65K - $75K/yr

Draft POSITION SUMMARY The Underwriter Trainee ("Trainee") participates in the commercial ... flexible spending, short-term and long-term disability insurance, life insurance, paid parental ...

Auto-Owners Insurance

Underwriter

Broomfield, CO · On-site

$59K - $89K/yr

Auto-Owners Insurance, a top-rated insurance carrier, is seeking a motivated underwriting trainee ... flexible spending accounts and dependent care flexible spending accounts. Additional benefits ...

Auto-Owners Insurance

Underwriter

Peoria, IL · On-site

$47K - $83K/yr

Auto-Owners Insurance, a top-rated insurance carrier, is seeking a motivated underwriting trainee ... flexible spending accounts and dependent care flexible spending accounts. Additional benefits ...

Auto Owners Insurance Company

Underwriter

Peoria, IL · On-site

$47K - $83K/yr

Auto-Owners Insurance, a top-rated insurance carrier, is seeking a motivated underwriting trainee ... flexible spending accounts and dependent care flexible spending accounts. Additional benefits ...

Rsli

Underwriter II

Philadelphia, PA · On-site

$68K - $85K/yr

Mentors Underwriting Trainees. Required Knowledge, Skills, Abilities and/or Related Experience ... Work location may be flexible if approved by the Company. What We Offer At Reliance Matrix, we ...

Reliance Matrix

Underwriter II

Philadelphia, PA · On-site

$68K - $85K/yr

Mentors Underwriting Trainees. Required Knowledge, Skills, Abilities and/or Related Experience ... Work location may be flexible if approved by the Company. What We Offer At Reliance Matrix, we ...

Rsli

Underwriter II

South Portland, ME · On-site

$68K - $85K/yr

Mentors Underwriting Trainees. Required Knowledge, Skills, Abilities and/or Related Experience ... Work location may be flexible if approved by the Company. What We Offer At Reliance Matrix, we ...

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Flexible Underwriter Trainee information

See salary details

$32.5K

$78.9K

$139.5K

How much do flexible underwriter trainee jobs pay per year?

As of Aug 26, 2026, the average yearly pay for flexible underwriter trainee in the United States is $78,878.00, according to ZipRecruiter salary data. Most workers in this role earn between $61,000.00 and $87,000.00 per year, depending on experience, location, and employer.

What are the most commonly searched types of Underwriter Trainee jobs?

The most popular types of Underwriter Trainee jobs are:

Flexible Underwriter Trainee jobs near you
Infographic showing various Flexible Underwriter Trainee job openings in the United States as of August 2026, with employment types broken down into 1% As Needed, 69% Full Time, 27% Part Time, and 3% Contract. Highlights an 80% Physical, 1% Hybrid, and 19% Remote job distribution, with an average salary of $78,878 per year, or $37.9 per hour.

Underwriting Trainee

IFG Companies

Chicago, IL • On-site

$65K - $75K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted 14 days ago

Job description

Draft

POSITION SUMMARY

The Underwriter Trainee ("Trainee") participates in the commercial underwriting trainee program of IFG Companies ("Companies"), building foundational skills in technical underwriting, sales and professional development while gaining direct exposure to wholesale insurance brokers across the U.S. The Trainee follows a structured on-the-job program that combines formal curriculum with real-world application across key lines of coverage, including General Liability, Excess Liability and Inland Marine. This opportunity is suited for recent graduates and early career professionals with an interest in commercial insurance underwriting and a commitment to professional development.

POSITION RESPONSIBILITIES INCLUDING

  • Completing a structured underwriting curriculum covering GL, Excess and IM, including self-study modules, facilitated training sessions, case studies and real-world application exercises.
  • Attending virtual and in-person training sessions and satisfactorily completing progressively challenging underwriting assignments, case studies and gated assessments throughout the program.
  • Coordinating with Companies’ mentors for structured on-the-job exposure, gaining hands-on experience in account management, submission review and risk assessment.
  • Developing key knowledge benchmarks in underwriting principles, risk assessment, pricing and strategic relationship management with wholesale insurance brokers.
  • Supporting the Companies’ underwriters in developing insurance solutions for a wide range of small and middle market clients.
  • Participating in regular coaching and mentor check-ins to track progress, address knowledge gaps and prepare for transition into a full production underwriting role.
  • Performing other duties, as requested.

KNOWLEDGE, SKILLS AND ABILITIES

  • Meticulous and disciplined attention to detail, with a commitment to accuracy in all underwriting work.
  • Strong academic performance and demonstrated intellectual curiosity.
  • Consistent work ethic and reliability in a fast-paced, deadline-driven environment.
  • Enthusiastic and passionate about the insurance industry, with a genuine interest in commercial underwriting.
  • Strong interpersonal skills and an entrepreneurial mindset, with the ability to build rapport with brokers, mentors, and colleagues.
  • Effective verbal and written communication skills, with the ability to convey underwriting rationale clearly and professionally.
  • Strong analytical and problem-solving skills, with the ability to interpret data and apply sound judgment to underwriting decisions.
  • Humility and the ability to receive constructive feedback, adapting quickly to coaching and mentorship.
  • Ability to manage multiple assignments and competing deadlines, functioning with increasing independence as the program progresses.
  • Collaborative, team-oriented mindset, with the ability to work effectively across departments and with external broker partners.
  • Excellent computer skills (e.g. Excel, Word, SharePoint) and the ability and willingness to learn the Companies’ proprietary systems.

EDUCATION, EXPERIENCE AND CERTIFICATIONS

  • Required: A bachelor's degree from an accredited U.S. college/university, with a major or coursework in insurance, risk management, economics, actuarial science, or related fields.
  • Required: Proficiency with Microsoft applications such as Outlook, Excel, PowerPoint, Word, Copilot and the ability to learn other business applications.
  • Required: Excellent written an verbal English communication skills.
  • Preferred: Industry-related summer internship or work experience.
  • Preferred: Demonstrated leadership, teamwork and a positive attitude toward learning through academic, extracurricular or work experiences.

PHYSICAL DEMANDS

  • Position is hybrid and requires the ability and the willingness to work in an IFG Companies office at least three (3) days per week if residing within one-hour commuting distance.
  • Physical demands are considered those of a climate-controlled office environment with minimal physical exertion.
  • Position requires prolonged sitting, extensive utilization of computers and interactions with others in person and via phone.
  • Position requires the ability and the willingness to travel when required to meet business needs.

SALARY AND BENEFITS

The salary range for this position is $65,000 to $75,000. Additionally, the position may be eligible to earn incentive compensation.

IFG Companies offers competitive compensation and benefits, currently including medical, dental, vision, 401(k), flexible spending, short-term and long-term disability insurance, life insurance, paid parental leave, vacation and other paid time off.

WHY IFG COMPANIES

Founded in 1985, IFG Companies is one of the oldest privately held insurance groups in the United States. It combines a specialty-carrier focus with long-term stability and thinking, while promoting a culture of underwriting rigor, collaboration, strategic thinking, superior technology and strong producer partnerships.

EQUAL OPPORTUNITY

IFG Companies is an equal opportunity employer. All applicants will be considered for employment without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status or any other protected characteristic under applicable law.


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