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Fleet Underwriter Jobs (NOW HIRING)

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Field Underwriting Representative

Boston, MA · On-site

$60K - $919K/yr

Massachusetts Property Insurance Underwriting Association is seeking a Field Underwriting ... Maintain and care for assigned fleet vehicle and Association's equipment. * Keep accurate records ...

Berkley

Fleet Safety Specialist

Jacksonville, FL · On-site

$70K - $130K/yr

... Underwriting with clear, concise, and timely reports to assist with decisions on pricing and account acceptability Analyze loss information to identify root causes and develop loss sensitive ...

Berkley

Fleet Safety Specialist

Jacksonville, FL · On-site

$70K - $130K/yr

The Fleet Safety Specialist provides risk management and safety services to trucking fleets within ... Underwriting with clear, concise, and timely reports to assist with decisions on pricing and ...

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$32.5K

$78.9K

$139.5K

How much do fleet underwriter jobs pay per year?

As of Aug 30, 2026, the average yearly pay for fleet underwriter 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 is a fleet underwriter?

A Fleet Underwriter is responsible for assessing and managing the risk associated with insuring a fleet of vehicles, typically for businesses or commercial clients. They evaluate applications, analyze claims history, and determine appropriate coverage and premium rates. Their role involves working closely with brokers, risk managers, and clients to ensure policies align with company guidelines and risk appetite. Strong analytical skills, industry knowledge, and attention to detail are essential to making informed underwriting decisions.

What does a fleet underwriter do?

A typical day for a Fleet Underwriter involves analyzing risk data for commercial vehicle fleets, reviewing insurance applications, and collaborating closely with brokers or agents to develop suitable coverage solutions. You’ll often use specialized underwriting tools and systems to assess risks and determine pricing, while also communicating underwriting decisions to internal teams and external partners. Regular tasks include evaluating loss histories, negotiating policy terms, and staying current on market trends and regulations. This dynamic environment combines independent analysis with frequent teamwork, making problem-solving and relationship-building key parts of the role.

What skills and qualifications are needed to be a fleet underwriter?

To excel as a Fleet Underwriter, you need strong analytical skills, in-depth knowledge of risk assessment and commercial auto insurance products, and a background in finance or insurance—often supported by a relevant degree or professional certifications like ACII or CPCU. Familiarity with underwriting software, fleet management systems, and industry databases is commonly required. Strong negotiation, decision-making, and communication skills set outstanding candidates apart in this role. These competencies are crucial for accurately evaluating fleet risks, maintaining profitable portfolios, and fostering positive relationships with clients and brokers.

Do fleet underwriters earn good money?

Fleet underwriters typically earn a competitive salary that varies based on experience, location, and employer size. They often receive benefits such as bonuses and may need industry certifications, with salaries generally reflecting the specialized risk assessment skills required for the role.
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What states have the most Fleet Underwriter jobs?

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Fleet Underwriter jobs near you
Infographic showing various Fleet Underwriter job openings in the United States as of August 2026, with employment types broken down into 1% As Needed, 91% Full Time, and 8% Part Time. Highlights an 99% Physical, and 1% Remote job distribution, with an average salary of $78,878 per year, or $37.9 per hour.

Commercial Specialty Auto Underwriter

Chicago, IL • On-site

RLI Corp.
Insurance Services • 1 - 5K employees
Learn more about RLI Corp.external

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 24 days ago

Job description

About UsWe're not like other insurance companies. From our specialty products to our business model, our culture to our results -we're different.Different is who we are, and how we work, interact, deliver and succeed together.Creating a different and better insurance experience doesn't just happen. It takes focus and a shared passion for going beyond the expected to forge relationships and deliver care that makes a difference. This approach rises from and is supported by our talented, ethical and smart team of employee owners united around a single purpose: to work alongside our customers and partners when they need us, in unexpected ways, with exceptional results. Apply today to make a difference with us.RLI is a Glassdoor Best Places to Work company with a strong, successful background. For decades, our financial track record has been stellar - a testament to our culture and validation of our reputation as an excellent underwriting company.Position PurposeUnder occasional supervision, underwrite new and renewal Commercial Specialty Auto accounts within the Transportation business. Evaluate and price risks while balancing profitability, growth, and customer service objectives. Develop strong relationships with agents and brokers, identify quality transportation risks, and apply sound underwriting judgment to build a profitable book of business. Review more complex submissions, loss experience, and pricing models while operating within assigned underwriting authority.Principal Duties & Responsibilities
  • Analyze, evaluate, price, quote, bind, decline, and renew Commercial Specialty Auto accounts with moderate to high premium volume and risk exposure.
  • Underwrite transportation risks in accordance with underwriting guidelines and authority levels.
  • Review submissions, loss history, financial information, driver and fleet characteristics, safety programs, and operational exposures to determine acceptability and pricing.
  • Apply underwriting judgment to evaluate risk quality, coverage structure, deductibles, pricing, and terms to achieve profitable growth.
  • Develop and maintain strong relationships with agents, brokers, reinsurers, and internal business partners to support production and service objectives.
  • Negotiate pricing, coverage, and terms with agency partners while maintaining underwriting discipline.
  • Monitor renewal business and recommend pricing or coverage changes based on loss trends, market conditions, and account performance.
  • Document underwriting decisions and maintain complete, accurate account files.
  • Assist with policy approvals, endorsements, renewals, and other policy servicing activities within assigned authority.
  • Participate in agency visits, marketing activities, and industry events to strengthen agency relationships and identify new business opportunities.
  • Assist with special projects and perform other duties as assigned.
Education & Experience
  • Typically requires a bachelor's degree in insurance, finance, risk management, business or a related field
  • Minimum of 3+ years of commercial P&C underwriting experience, preferably with Commercial Specialty Auto or Excess & Surplus (E&S) Transportation accounts
  • [OR] equivalent level of education and experience
Knowledge, Skills, & Competencies
  • Knowledge of Commercial Specialty Auto and/or E&S Transportation underwriting principles, including operations, risk selection, pricing, and coverage evaluation.
  • Ability to analyze transportation exposures, loss experience, financial information, and pricing models to make sound underwriting decisions.
  • Strong understanding of commercial insurance coverage, policy forms, and underwriting guidelines.
  • Ability to evaluate driver, vehicle, fleet, and operational characteristics to assess risk quality.
  • Strong analytical and problem-solving skills with the ability to balance production goals and profitability.
  • Excellent verbal and written communication skills with the ability to explain underwriting decisions and negotiate effectively with agency partners.
  • Ability to build and maintain productive relationships with agents, brokers, reinsurers, and internal stakeholders.
  • Ability to prioritize multiple accounts and manage competing deadlines in a fast-paced environment.
  • Proficient with underwriting systems and technology used to analyze risk and manage a book of business.
  • Demonstrates sound underwriting judgment and typically possesses underwriting letter of authority appropriate for the role.
  • Participates in continuing education and remains current on transportation industry trends, regulatory developments, and market conditions.
  • Works independently on moderately complex risks and escalates unique or non-standard issues when appropriate.
Compensation OverviewThe base salary range for the position is listed below. Please note that the base salary is only one component of our robust total rewards package at RLI. The salary offered will take into account a number of factors including, but not limited to, geographic location, experience, scope & responsibilities of the role, qualifications/credentials, talent availability & specialization, as well as business needs. The below range may be modified in the future. Base Pay Range$77,025.00 - $109,145.00Total RewardsAt RLI, we're all owners. We hire the best and the brightest employees and allow them to share in the company's success through our Total Rewards. With the Employee Stock Ownership plan at its core, the Total Rewards program includes all compensation, benefits and perks that come with being an RLI employee.Financial Incentives
  • Annual bonus plans
  • Employee stock ownership plan (ESOP)
  • 401(k) - automatic 3% company contribution
  • Annual 401k and ESOP profit-sharing contributions (Up to 15% of eligible earnings)
Work & Life
  • Paid time off (PTO) and holidays
  • Paid volunteer time off (VTO) to support our communities
  • Parental and family care leave
  • Flexible & hybrid work arrangements
  • Fitness center discounts and free virtual fitness platform
  • Employee assistance program
Health & Wellness
  • Comprehensive medical, dental and vision benefits
  • Flexible spending and health savings accounts
  • 2x base salary for group life and AD&D insurance
  • Voluntary life, critical illness, & accident insurance for purchase
  • Short-term and long-term disability benefits
Personal & Professional GrowthRLI encourages its employees to pursue professional development work in insurance and job-related areas. We make a commitment to employees to provide educational opportunities that help them enhance their skills and further their career advancement. RLI fosters a true learning culture and encourages professional growth through insurance courses, in-house training and other educational programs. RLI covers the cost for most programs and employees typically earn a bonus upon successful completion of approved courses and certifications. Our personal and professional growth benefits include:
  • Training & certification opportunities
  • Tuition reimbursement
  • Education bonuses
Diversity & InclusionOur goal is to attract, develop and retain the best employee talent from diverse backgrounds while promoting an environment where all viewpoints are valued and individuals feel respected, are treated fairly, and have an opportunity to excel in their chosen careers. We actively support, and participate in, initiatives led by the American Property Casualty Insurance Association that aim to increase diversity in the insurance industry. Cultivating an exceptional and diverse workforce to deliver excellent customer service reinforces our culture and is a key to achieving superior business results.RLI is an equal opportunity employer and does not discriminate in hiring or employment on the basis of race, color, religion, national origin, citizenship, gender, marital status, sexual orientation, age, disability, veteran status, or any other characteristic protected by federal, state, or local law.
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About RLI

Sourced by ZipRecruiter

Industry

Insurance services

Company size

1,001 - 5,000 Employees

Headquarters location

Peoria, IL, US

Year founded

1965

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