Sr. Underwriter - Executive Products (Wholesale)

RLI Insurance Company; Chicago (IL); Hybrid; USD 111,000 - 156,000; Full time

Benefits offered by this job

Annual bonus plans

Employee stock ownership plan (ESOP)

401(k) — automatic 3% company contrib.

Annual profit-sharing contributions (≤

Job summary

RLI Insurance Company is seeking an experienced underwriter to own and grow a profitable Management Liability portfolio. You will independently evaluate complex risks, make timely underwriting decisions, and build strong broker relationships to drive growth in the Wholesale Division.

You will produce well-documented files and collaborate with internal partners to support profitable expansion while balancing priorities in a fast-paced environment.

Qualifications

• Bachelor's degree or equivalent experience.
• 5+ years of commercial underwriting experience, preferably in Management Liability.
• Demonstrated success managing a profitable book of business and building strong broker relationships.
• RPLU designation preferred.

Responsibilities

• Analyze, quote, bind, and manage new and renewal Management Liability submissions within underwriting authority.
• Build trusted relationships with Wholesale Brokers through responsive communication, consistent follow-through, and thoughtful underwriting decisions.
• Exercise strong underwriting judgment by evaluating financial, operational, legal, and management exposures to determine acceptable risks.
• Produce accurate, well-documented underwriting files, pricing rationale, and policy documentation requiring minimal rework.
• Effectively prioritize new business, renewals, and operational responsibilities while meeting service standards and internal deadlines.
• Collaborate with internal partners to support profitable growth and continuous process improvement.

Skills

Underwriting judgment

Broker relationships

Analytical thinking

Communication skills

Negotiation

Prioritization

Attention to detail

Independent decision‑making

Learning mindset

Education

Bachelor's degree or equivalent experience

RPLU designation preferred

Job description

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.

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

Own and grow a profitable portfolio of Management Liability business through disciplined underwriting, sound judgment, and exceptional broker relationships. The successful candidate will independently evaluate complex risks, make timely underwriting decisions, and deliver a high-quality work product while contributing to the continued growth and profitability of the Wholesale Division.

Principal Duties & Responsibilities

• Analyze, quote, bind, and manage new and renewal Management Liability (D&O, EPL, etc) submissions within underwriting authority.
• Build trusted relationships with Wholesale Brokers through responsive communication, consistent follow-through, and thoughtful underwriting decisions.
• Exercise strong underwriting judgment by evaluating financial, operational, legal, and management exposures to determine acceptable risks.
• Produce accurate, well-documented underwriting files, pricing rationale, and policy documentation requiring minimal rework.
• Effectively prioritize new business, renewals, and operational responsibilities while meeting service standards and internal deadlines.
• Collaborate with internal partners to support profitable growth and continuous process improvement.

Education & Experience

• Bachelor's degree or equivalent experience.
• 5+ years of commercial underwriting experience, preferably in Management Liability.
• Demonstrated success managing a profitable book of business and building strong broker relationships.
• RPLU designation preferred

Knowledge, Skills, & Competencies

• Sound underwriting judgment and analytical thinking.
• Strong knowledge of Management Liability products and underwriting strategy.
• Excellent communication and negotiation skills.
• Exceptional attention to detail and organizational skills.
• Ability to manage competing priorities in a fast-paced environment.
• Accountability, ownership, and independent decision-making.
• Intellectual curiosity and a commitment to continuous learning.
• Relationship builder with strong marketing instincts and the ability to create trusted partnerships that generate profitable business

What Success Looks Like

• Builds trusted broker relationships that generate repeat business.
• Makes timely, well-reasoned underwriting decisions aligned with company strategy.

  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

  $111,357.00 - $156,093.00

  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.

  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.