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Director Stop Loss Underwriter Jobs (NOW HIRING)

Berkley

Stop Loss Underwriter

Trenton, NJ · Remote

$90K - $110K/yr

As a Stop Loss Underwriter, you will seek profitable growth of the company's portfolio of stop loss business by analyzing and selecting risks based on qualified underwriting criteria that adhere to ...

Acrisure

Stop Loss Underwriter

Las Vegas, NV · On-site +1

$60K - $85K/yr

The 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 ...

Novacore

Underwriter, Stop Loss

Conshohocken, PA · On-site

$100 - $140/hr

Possibility of some active distribution sources may be directed to the Senior Medical Stop-Loss Underwriter. Someone in this position must develop distribution sources and foster a dynamic ...

Berkley

Stop Loss Underwriter

Trenton, NJ · On-site

$90K - $110K/yr

As a Stop Loss Underwriter, you will seek profitable growth of the company's portfolio of stop loss business by analyzing and selecting risks based on qualified underwriting criteria that adhere to ...

Berkley

Stop Loss Underwriter

Trenton, NJ · Remote

$90K - $110K/yr

As a Stop Loss Underwriter, you will seek profitable growth of the company's portfolio of stop loss business by analyzing and selecting risks based on qualified underwriting criteria that adhere to ...

Berkley

Senior Stop Loss Underwriter

Indianapolis, IN · On-site

$90K - $120K/yr

As a Sr. Stop Loss Underwriter , we'll trust you to seek profitable growth of the company's portfolio of stop loss business by analyzing and selecting risks based on qualified underwriting criteria ...

Acrisure

Senior Stop Loss Underwriter

Chicago, IL · On-site +1

$90K - $125K/yr

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 ...

Berkley

Senior Stop Loss Underwriter

Indianapolis, IN · Remote

$90K - $120K/yr

As a Sr. Stop Loss Underwriter , we'll trust you to seek profitable growth of the company's portfolio of stop loss business by analyzing and selecting risks based on qualified underwriting criteria ...

Acrisure

Senior Stop Loss Underwriter

Stevens Point, WI · On-site +1

$90K - $125K/yr

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 ...

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Director Stop Loss Underwriter information

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$62K

$140K

$206K

How much do director stop loss underwriter jobs pay per year?

As of Sep 5, 2026, the average yearly pay for director stop loss underwriter in the United States is $140,035.00, according to ZipRecruiter salary data. Most workers in this role earn between $100,000.00 and $168,500.00 per year, depending on experience, location, and employer.

What does a director stop loss underwriter do?

A Director Stop Loss Underwriter oversees the underwriting process for stop loss insurance policies, which protect employers or health plans from large claims by covering costs above a certain threshold. This role involves evaluating risks, setting premium rates, and developing strategies to manage large claim exposures. Directors also supervise underwriting teams, ensure compliance with regulations, and work closely with brokers, clients, and actuaries to create customized stop loss solutions. Their expertise helps employers manage healthcare costs and financial risks associated with self-funded health plans.

What are the key skills and qualifications needed to thrive as a director stop loss underwriter?

To thrive as a Director Stop Loss Underwriter, you need in-depth knowledge of medical stop loss insurance, risk assessment, and underwriting principles, typically supported by a bachelor’s degree in finance, business, or a related field. Proficiency with underwriting software, data analytics tools, and familiarity with regulatory compliance systems is essential. Strong leadership, negotiation, and decision-making skills, along with effective communication, set exceptional professionals apart in this role. These skills and qualities are vital for accurately evaluating risk, ensuring profitable portfolios, and leading teams in a complex insurance environment.

What are the main challenges faced by a director stop loss underwriter and how can they be managed effectively?

One of the primary challenges in this role is balancing risk assessment with competitive pricing, as the stop-loss market is highly dynamic and client needs are diverse. Directors must stay updated on emerging trends in healthcare costs, regulatory changes, and claims data analytics to make informed underwriting decisions. Collaborating closely with actuarial, sales, and claims teams is essential to ensure that underwriting strategies align with business goals and market demands. Regular communication and ongoing professional development help manage these challenges and contribute to long-term success.

What is the difference between Director Stop Loss Underwriter vs Underwriting Manager?

AspectDirector Stop Loss UnderwriterUnderwriting Manager
CredentialsTypically requires actuarial or underwriting certifications, bachelor's degree in finance or related fieldSimilar credentials, often with underwriting or actuarial certifications, bachelor's degree required
Work EnvironmentFocuses on risk assessment and pricing for stop loss insurance, often in insurance companies or brokersOversees underwriting teams, manages policies, and ensures compliance within insurance firms
Industry UsageCommonly used in health, life, and property & casualty insurance sectorsWidely used across various insurance lines, including health and property insurance

The main difference is that the Director Stop Loss Underwriter specializes in evaluating and pricing stop loss insurance policies, often leading risk assessment teams. In contrast, the Underwriting Manager oversees broader underwriting operations and team management. Both roles require similar credentials and are integral to insurance companies, but their focus areas and responsibilities differ.

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Director Stop Loss Underwriter jobs near you
Infographic showing various Director Stop Loss Underwriter job openings in the United States as of August 2026, with employment types broken down into 100% Full Time. Highlights an 78% In-person, 11% Hybrid, and 11% Remote job distribution, with an average salary of $140,035 per year, or $67.3 per hour.

Stop Loss Underwriter

Strategic Staffing Solutions

Minneapolis, MN

$40 - $58/hr

Full-time

Posted 16 days ago

Key responsibilities

  • Underwrite new and renewal Employer Medical Stop Loss business.

  • Evaluate coverage options, analyze group demographics, claims experience, and risk factors to inform underwriting decisions.

  • Partner with internal stakeholders and manage underwriting activities to meet established turnaround times.

Job description

Job Description Medical Stop Loss Group Underwriter | Associate, Senior & Lead Location: Minneapolis, MN / Hybrid Preferred Employment Type: W-2 Contract Contract Duration: Through December 31, 2026 Opportunity: Multiple Openings Strategic Staffing Solutions (S3) is seeking experienced Medical Stop Loss Group Underwriters for multiple opportunities with a leading financial services and employee benefits organization. We are recruiting across Associate, Senior, and Lead Group Underwriter levels. Level will be determined based on Medical Stop Loss experience, complexity and size of groups underwritten, and individual underwriting authority.

This is an excellent opportunity for professionals with experience in Employer Stop Loss, Medical Stop Loss, self-funded health plans, Specific and Aggregate Stop Loss, group underwriting, or health reinsurance. Medical Stop Loss Underwriter Responsibilities Underwrite new and renewal Employer Medical Stop Loss business Evaluate Specific and Aggregate Stop Loss coverage Analyze group demographics, historical claims experience, large claimants, plan design, participation, and overall medical and financial risk Evaluate high-cost claimants and determine appropriate underwriting actions, including individual lasers, when applicable Develop pricing, rates, deductibles, contract terms, and underwriting recommendations Analyze account profitability while balancing competitive pricing with appropriate risk selection Review underwriting submissions and supporting claims and financial data Make independent underwriting decisions within established authority levels and escalate cases when appropriate Partner with brokers, sales, account management, actuarial, clinical, and other internal stakeholders Manage new business and renewal activity while meeting established turnaround expectations Qualifications Qualified candidates should have experience in one or more of the following areas: Medical Stop Loss underwriting Employer Stop Loss underwriting Specific and Aggregate Stop Loss Self-funded or ASO employer health plans Group health underwriting Health insurance or reinsurance underwriting Medical claims and large claimant analysis Stop Loss pricing and financial risk analysis New business and renewal underwriting Individual claimant or laser evaluation Experience level and underwriting authority will be considered when determining alignment with the Associate, Senior, or Lead Group Underwriter level. Candidates should be comfortable discussing the largest employer groups/lives they have personally underwritten, individual underwriting authority, case complexity, and experience with Specific and Aggregate Stop Loss coverage.

What We're Looking For We are especially interested in Medical Stop Loss professionals who can bring strong analytical judgment and practical knowledge of the self-funded employer health insurance market. Successful candidates will understand how claims experience, large claimants, medical risk, plan design, contract provisions, deductibles, pricing, and financial exposure come together in an Employer Stop Loss underwriting decision. Work Arrangement Hybrid in Minneapolis is preferred.

Candidates should be commutable to the Minneapolis location if converting to permanent employment. Strong Medical Stop Loss candidates who require a different work arrangement may still be considered based on experience and business needs. Why Apply.

Medical Stop Loss is a highly specialized area, and we are interested in speaking with professionals at multiple career levels. If your background includes Employer Stop Loss, Medical Stop Loss, self-funded health plans, Specific/Aggregate coverage, or Stop Loss reinsurance, we encourage you to apply. Apply today to be considered for one of several Medical Stop Loss Group Underwriter openings.

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