Jobs › RLI Corp

Underwriting/Operations Assistant - Commercial Property

RLI Corp · Chicago, IL · $22.01–$29.29 an hour · Full time

Posted Jul 16, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a time you handled a lot of detailed documents and kept them accurate.

What they are checking: Whether they have the attention to detail that creating policy documents and keeping files depends on.

Tell me about a time you learned the rules or regulations for a new type of work.

What they are checking: Whether they can learn compliance requirements and follow them consistently.

Tell me about a time you gave great support to a team or coworker.

What they are checking: Whether they take pride in support work and make others' jobs easier.

What interests you about working in insurance operations?

What they are checking: Whether they have a real reason for wanting this role and are likely to stay and grow.

What would you do

You notice an insurance certificate doesn't match what is on the policy. What do you do?

What they are checking: Whether they catch discrepancies and resolve them before they become problems for an insured.

Several underwriters ask you for help at the same time. How do you decide what to do first?

What they are checking: Whether they can prioritize by urgency and ask for clarity rather than guessing.

What would you do if you were unsure whether a policy form met a regulatory requirement?

What they are checking: Whether they ask for guidance rather than guessing, since compliance mistakes carry real risk.

About the work

What do you know about inspections and premium audits, and why would an underwriter need them?

What they are checking: Whether they understand how inspections and audits help price and manage risk accurately.

How do you keep track of renewal deadlines so nothing falls through the cracks?

What they are checking: Whether they have a reliable system for time-sensitive work like soliciting renewals.

How comfortable are you with Microsoft Office and learning new systems?

What they are checking: Whether they can handle the electronic files and systems the role depends on daily.

Practice this interview out loud.

Offer builds a real interview for this exact role at RLI Corp from your resume and this job description, asks the questions one at a time, and tells you what landed. The first one is free.

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The full job description

As published by RLI Corp.

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 Support Commercial Property underwriting by creating policy documents, ensure compliance with regulatory requirements, order inspections and premium audits, maintain electronic underwriting files, solicit renewal transactions, provide basic operational support for the product line’s underwriters. Review insurance certificates, resolving discrepancies with reinsurers, providing operations, production, and underwriting reports, working with producers, audit work of others, given authority in some cases on behalf of Underwriting. Principal Duties & Responsibilities • Create policy documents which represent the insurance transaction bound by the underwriter. • Ensure the statistical coding and policy issuance complies with regulatory requirements for each insurance transaction. • Order inspections, premium audits, and loss runs as required. • Maintain electronic underwriting file. • Solicit renewal transactions. • As necessary, re-format data for import into front end system. • Provide basic operational support for the product line’s underwriters. • As requested by underwriters, develop underwriting information from the internet and other data sources. • Review facultative insurance certificates to ensure the terms identified by the reinsurer are consistent with terms expected by underwriter. • Resolve accounting discrepancies with facultative reinsurers. • Provide operational, production, and underwriting reports to underwriting staff as requested, utilizing front-end systems and/or Business Objects. • Contact producers to determine appropriate courses of action. • Assist with User Acceptance Testing of systematic changes. • Audit the work of others. • May be given authority to review/approve endorsements, review/analyze risks, review terms and conditions of underlying policies, review inspections of risks, each of which would be on behalf of Underwriting. Education & Experience • Typically requires a high school diploma; Associates degree preferred • 2+ years of related experience for consideration • [OR] equivalent level of education and experience • Experience in commercial property insurance preferred Knowledge, Skills, & Competencies • Ability to follow operations procedures as outlined by supervisor/manager. • Ability to meet processing deadlines with minimal error. • Ability to manage a variety of projects, both long- and short-term simultaneously. • Ability to use database software including Windows operating systems, computer network environment and printers to process insurance policy changes. • Accurate data entry. • Superior Excel skills to peer review formulas, formatting, and data cleansing of large spreadsheets. 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 $22.01 - $29.29 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 completion of approved courses and certifications. Our personal and professional growth benefits include: • Training & certification opportunities • Tuition reimbursement • Education bonuses Diversity & Inclusion Our 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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