Trucking Transportation Underwriter

About Us

We’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 Purpose

Under general oversight, underwrite and manage a profitable book of commercial transportation business, primarily focused on mid-sized trucking fleets. Evaluate complex new and renewal accounts, apply sound underwriting judgment, and make risk selection, pricing, and coverage decisions within assigned authority. Develop strong relationships with agents and brokers to increase submission flow and identify profitable new business opportunities. Maintain ownership and accountability for portfolio performance while balancing growth, profitability, and underwriting discipline.

Principal Duties & Responsibilities

Analyze, evaluate, accept, decline, rate, quote, and bind complex new and renewal commercial transportation accounts within assigned underwriting authority.

Evaluate trucking operations, loss experience, driver and fleet characteristics, safety practices, financial information, and other relevant exposures to determine risk acceptability, pricing, terms, and conditions.

Develop and maintain strong relationships with agents and brokers to generate quality submission flow, retain profitable business, and identify new business opportunities.

Manage an assigned book of business with accountability for growth, profitability, rate adequacy, retention, and overall portfolio performance.

Review complex submissions, account loss experience, pricing models, and other underwriting information to identify profitable risk opportunities.

Negotiate pricing, coverage, terms, and conditions with agents and brokers while maintaining underwriting discipline and product appetite.

Monitor individual account and portfolio performance and respond appropriately to changes in loss trends, exposure, market conditions, or risk quality.

Maintain complete and organized underwriting files with clear documentation supporting risk selection, pricing, and underwriting decisions.

Exercise independent judgment on complex and non-standard underwriting matters and present recommendations to management when appropriate.

Collaborate with underwriting leadership and internal business partners on market, product, agency, and portfolio initiatives.

Assist with special projects or other duties as assigned.

Education & Experience

Typically requires a bachelor's degree in insurance, finance, risk management, business, or a related field.

Minimum of 2 years of commercial trucking transportation underwriting experience.

Experience underwriting fleet or other complex commercial auto risks preferred.

Experience developing producer relationships and managing a profitable book of business preferred.

Equivalent combination of education and experience will be considered.

Knowledge, Skills, & Competencies

Strong knowledge of commercial transportation underwriting principles, including risk selection, pricing, coverage, and portfolio management.

Ability to evaluate trucking operations and exposures, including fleet composition, driver quality, loss experience, safety practices, operating characteristics, and other factors affecting risk quality.

Strong analytical skills with the ability to interpret loss information, pricing models, exposure data, and other underwriting information to make sound decisions.

Demonstrates sound underwriting judgment and the ability to independently evaluate complex and non-standard risks within assigned authority.

Thorough understanding of product appetite, underwriting guidelines, submission requirements, pricing methodologies, and internal underwriting processes.

Ability to build and maintain productive relationships with agents and brokers and effectively develop quality submission flow.

Strong negotiation skills with the ability to balance producer relationships, customer needs, and underwriting objectives.

Ability to manage and maintain a profitable book of business while balancing growth, retention, rate adequacy, and risk quality.

Ability to clearly communicate underwriting decisions, findings, and recommendations to internal and external business partners, both verbally and in writing.

Ability to identify changing risk characteristics, loss trends, and market conditions and adjust underwriting strategies appropriately.

Maintains complete and organized underwriting documentation so that risk selection, pricing, and underwriting judgment are clearly supported.

Ability to effectively utilize underwriting systems, data, and analytical tools to evaluate accounts and portfolio performance.

Demonstrates initiative, accountability, and the ability to work independently on complex underwriting matters.

Typically possesses an appropriate level of underwriting authority and demonstrates readiness for increased authority based on experience and performance.

Participates in underwriting-related continuing education and maintains knowledge of transportation industry and insurance market trends.

Compensation Overview

The 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 - $109,145.00

Total Rewards

At 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 Growth

RLI 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