Transportation Underwriter, Commercial Lines

Position Summary

We are seeking a Transportation Underwriter to support our growing Commercial Transportation portfolio. This role evaluates, analyzes, and underwrites complex risks across key transportation lines, ensuring proper risk selection, pricing accuracy, and compliance with binding authority and carrier guidelines.

The ideal candidate has experience in transportation underwriting, GA/MGA environments, and working across multiple carriers. The position requires strong technical underwriting skills, attention to detail, and the ability to build strong relationships with agents and carrier partners.

The ideal candidate will work on a hybrid basis out of our Arlington Heights, IL office (85 W. Algonquin Road Suite 300 Arlington Heights, IL 60005)

Remote opportunity and/or senior title available dependent upon experience.

What will your job entail?

Underwriting & Risk Evaluation

• Evaluate, analyze, and underwrite complex commercial transportation risks within delegated authority.
• Review all submission information including exposures, loss runs, classification, and documentation.
• Apply correct rates, coverage forms, policy language, endorsements, exclusions, and carrier rules.
• Coordinate quoting, binding, issuance, and policy servicing to ensure accuracy and timeliness.
• Issue notices of cancellation, non‑renewal, and reinstatement per regulatory and carrier standards.
• Maintain accurate and complete file documentation for audit and compliance.

Portfolio & Production Management

• Manage a profitable portfolio of transportation accounts within assigned premium thresholds.
• Monitor account performance and take corrective action to maintain underwriting profitability.
• Track production goals, new business hit ratios, retention, and rate objectives.

Agency/Broker/Carrier Relationship Management

• Build and maintain strong working relationships with agents, producers, brokers, and carrier partners.
• Represent the company in marketing activities and meetings to generate new business.
• Collaborate with internal underwriters and senior team members to improve workflow and account strategy.

Team Collaboration & Projects

• Participate in weekly team meetings and ongoing team collaboration.
• Contribute to internal projects, process improvements, or underwriting initiatives as assigned.

Required Qualifications

• 2+ years of experience in Transportation Underwriting strongly preferred; Commercial lines considered.
• Must be licensed in Property and Casualty or willing to obtain licensing within 45 days.

Preferred Qualifications

• Bachelor's degree preferred (Risk Management, Business, Finance, or related field).
• MGA / GA experience highly beneficial.
• Strong analytical and problem‑solving skills.
• Highly detail‑oriented with strong organizational skills.
• Ability to manage multiple carriers, workflows, and agency relationships.
• Excellent communication skills (verbal and written)

Ryan Specialty is an Equal Opportunity Employer. We are committed to building and sustaining a diverse workforce throughout the organization. Our vision is an inclusive and equitable workplace where all employees are valued for and evaluated on their performance and contributions. Differences in race, creed, color, religious beliefs, physical or mental capabilities, gender identity or expression, sexual orientation, and many other characteristics bring together varied perspectives and add value to the service we provide our clients, trading partners, and communities. This policy extends to all aspects of our employment practices, including but not limited to, recruiting, hiring, discipline, firing, promoting, transferring, compensation, benefits, training, leaves of absence, and other terms, conditions, and benefits of employment.

How We Support Our Teammates

Ryan Specialty seeks to offer our employees a comprehensive and best-in-class benefits package that helps them — and their family members — achieve their physical, financial, and emotional well-being goals. In addition to paid time off for company holidays, vacation, sick and personal days, Ryan offers paid parental leave, mental health services and more.

The target salary range for this position is $78,400.00 - $98,000.00 annually.

The wage range for this role considers many factors, such as training, transferable skills, work experience, licensure and certification, business needs, and market demands. The pay range is subject to change and may be modified in the future. Full-time roles are eligible for bonuses and benefits. For additional information on Ryan Specialty Total Rewards, visit our website

We provide individuals with disabilities reasonable accommodations to participate in the job application or interview process, to perform essential job functions, and to receive other benefits and privileges of employment in accordance with applicable law. Please contact us to request an accommodation at [email protected]

The above is intended to describe this job's general requirements. It is not to be construed as an exhaustive statement of duties, responsibilities, or physical requirements. Nothing in this job description restricts management's right to assign or reassign duties and responsibilities to this job at any time. Reasonable accommodations may be made to enable individuals with disabilities to perform essential functions.