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Sr. Underwriter - Executive Products

RLI Insurance Company
Chicago, IL Full Time
POSTED ON 12/6/2025 CLOSED ON 2/28/2026

What are the responsibilities and job description for the Sr. Underwriter - Executive Products position at RLI Insurance Company?

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 occasional oversight, this role is responsible for underwriting within RLI’s Executive Products Group (EPG) wholesale team, with a primary focus on Directors & Officers Liability, Employment Practices Liability, Fiduciary Liability, Crime, and related management liability coverages. The underwriter will underwrite a diverse portfolio across public, private, and nonprofit organizations distributed through wholesale brokerage channels.

This position requires strong financial and risk analysis skills to assess complex exposures, design tailored coverage solutions and drive profitable growth of the wholesale portfolio. Success in the role also hinges on the ability to market RLI’s capabilities effectively, developing and sustaining strong broker relationships to expand our presence in the wholesale marketplace.

Principal Duties & Responsibilities


  • Perform all aspects of the underwriting process - maintaining proper authority, underwriting file integrity and adherence to strategy.
  • Analyze, evaluate, accept, decline, rate, quote, and bind new and renewal submissions across public, private, and nonprofit risks.
  • Conduct in-depth financial statement analysis and assess governance structures to inform risk selection and pricing.
  • Develop and execute a marketing plan that highlights our products and capabilities, fostering strong, trust-based relationships with brokers and clients to drive new business opportunities and renewal retention.
  • Collaborate with actuarial, claims, and product development teams


Education & Experience


  • Bachelor’s degree in business, finance, insurance, or a related field required.
  • 5–10 years of underwriting experience in management liability, with demonstrated expertise in D&O across public, private, and nonprofit entities. Wholesale distribution experience preferred.
  • Advanced degree, RPLU, CPCU, or other professional designation preferred.


Knowledge, Skills, & Competencies


  • Strong financial acumen with ability to analyze complex financial statements and market data.
  • Ability to communicate underwriting decisions and recommendations clearly to brokers and internal stakeholders.
  • Demonstrated leadership and mentoring skills to support team growth and performance.
  • Proficiency in underwriting systems and tools for evaluating, tracking, and managing accounts.
  • Strategic perspective with ability to balance risk selection, pricing discipline, and broker relationships to achieve profitability goals.


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

$104,211.00 - $149,022.00

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 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.

Salary : $104,211 - $149,022

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