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Senior Stop Loss Underwriter

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: Acrisure
Full Time position
Listed on 2026-08-20
Job specializations:
  • Insurance
    Underwriter, Insurance Analyst, Insurance Risk / Loss Control
Salary/Wage Range or Industry Benchmark: 110000 - 125000 USD Yearly USD 110000.00 125000.00 YEAR
Job Description & How to Apply Below

Job Description

About Acrisure

A global fintech leader, Acrisure empowers millions of ambitious businesses and individuals with the right solutions to grow boldly forward. Bringing cutting‑edge technology and top‑tier human support together, we connect clients with customized solutions across a range of insurance, reinsurance, payroll, benefits, cybersecurity, mortgage services – and more.

In the last twelve years, Acrisure has grown in revenue from $38 million to almost $5 billion and employs over 19,000 colleagues in more than 20 countries. Acrisure was built on entrepreneurial spirit. Prioritizing leadership, accountability, and collaboration, we equip our teams to work at the highest levels possible.

Job Summary:

The Senior Stop Loss Underwriter is responsible for evaluating, pricing, and managing risk for employer-sponsored self-funded health plans. This role includes underwriting both new business and renewals, assessing specific and aggregate exposure, and ensuring profitability while maintaining competitive positioning in the marketplace.

The Senior Stop Loss Underwriter collaborates with sales, clinical, policy, and claims teams to deliver sound underwriting decisions aligned with company guidelines and financial objectives.

Responsibilities:

  • Review employer census data, claims experience, and large claimant reports
  • Evaluate specific and aggregate risk exposure and establish appropriate attachment points, lasers, and aggregate corridors
  • Price stop loss coverage in accordance with underwriting guidelines
  • Analyze emerging large claims and assess recurrence risk
  • Underwrite new employer groups seeking stop loss coverage
  • Analyze renewal performance and determine rate adjustments
  • Balance competitiveness with profitability targets
  • Provide alternative quoting strategies when appropriate
  • Communicate underwriting decisions clearly and professionally with producers
  • Support producers during negotiations
  • Partner with clinical underwriting on high-cost cases
  • Coordinate with policy administration to ensure accurate contract terms
  • Adhere to delegated underwriting authority
  • Ensure compliance with state and federal regulations
  • Provide guidance and mentorship to junior underwriters.
  • Contribute to underwriting best practices, process improvements, and training initiatives.
  • Serve as a subject matter expert on complex or high-risk cases.

Requirements:

  • 5+ years of stop loss underwriting experience (specific & aggregate preferred)
  • Strong knowledge of self-funded health plan structures
  • Experience reviewing large claimant reports and medical diagnoses
  • Proficiency in underwriting models and rating tools

#LI-Remote

#LI-SS1

Pay Details:

The base compensation range for this position is $110,000 - $125,000. This range reflects Acrisure’s good faith estimate at the time of this posting. Placement within the range will be based on a variety of factors, including but not limited to skills, experience, qualifications, location, and internal equity.

Candidates should be comfortable with an on-site presence to support collaboration, team leadership, and cross-functional partnership.

Why Join Us:

At Acrisure, we’re building more than a business, we’re building a community where people can grow, thrive, and make an impact. Our benefits are designed to support every dimension of your life, from your health and finances to your family and future.

Making a lasting impact on the communities it serves, Acrisure has pledged more than $22 million through its partnerships with Corewell Health Helen DeVos Children’s Hospital in Grand Rapids, Michigan, UPMC Children’s Hospital in Pittsburgh, Pennsylvania and Blythedale Children’s Hospital in Valhalla, New York.

Employee Benefits

We also offer our employees a comprehensive suite of benefits and perks, including:

  • Physical Wellness: Comprehensive medical insurance, dental insurance, and vision insurance; life and disability insurance; fertility benefits; wellness resources; and paid sick time.

  • Mental Wellness: Generous paid time off and holidays;
    Employee Assistance Program (EAP); and a complimentary Calm app subscription.

  • Financial Wellness: Immediate vesting in a 401(k) plan;
    Health Savings Account (HSA) and Flexible…

Position Requirements
10+ Years work experience
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