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Director Stop Loss Underwriter Jobs (NOW HIRING)

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 ...

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 ...

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 ...

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 ...

Stop Loss Underwriter

Stevens Point, WI · 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 ...

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 ...

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 ...

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 ...

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 ...

Senior Stop Loss Underwriter

Las Vegas, NV · 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 ...

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 ...

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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 Aug 26, 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.

More about Director Stop Loss Underwriter jobs

What cities are hiring for Director Stop Loss Underwriter jobs?

Cities with the most Director Stop Loss Underwriter job openings:

What are the most commonly searched types of Stop Loss Underwriter jobs?

The most popular types of Stop Loss Underwriter jobs are:

What states have the most Director Stop Loss Underwriter jobs?

States with the most job openings for Director Stop Loss Underwriter jobs include:

Infographic showing various Director Stop Loss Underwriter job openings in the United States as of August 2026, with employment types broken down into 2% As Needed, 83% Full Time, 12% Part Time, 1% Temporary, and 2% Contract. Highlights an 91% Physical, 3% Hybrid, and 6% Remote job distribution, with an average salary of $140,035 per year, or $67.3 per hour.

Stop Loss Underwriter

Trenton, NJ • Remote

$90K - $110K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted 6 days ago


Job description

Berkley Accident and Health is a risk management company that designs innovative solutions to address the unique challenges of each client. With our entrepreneurial culture and a strong emphasis on analytics, we can help employers better manage their risk. We offer a broad range of products, including employer stop loss, benefit captives, provider stop loss, HMO reinsurance, and specialty accident. The key to Berkley’s success is our nimble approach to risk – our ability to quickly understand, think through, and devise a plan that addresses each client’s challenges, coupled with the strong backing of a Fortune 500 company. Our parent company, W. R. Berkley Corporation, is one of the largest and best managed property/casualty insurers in the United States.

  #LI-AV1 #LI-remote

The company is an equal employment opportunity employer.


This position can either be fully remote (if not within commutable distance to the office) or based in one of our offices:

  • Hamilton Square, NJ
  • Marlborough, MA
  • West Hartford, CT
  • Harleysville, PA

Our offices offer a hybrid work schedule with 4 days in the office; and 1 day remote where it makes sense to do so.

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 the company’s established underwriting guidelines. You will work closely with more seasoned underwriting staff to develop more advanced underwriting acumen over time. You'll gain a more thorough understanding of the Company’s clinical, actuarial, claims and distribution departments, all of which will advance the Underwriter’s experience and judgement levels.

You'll work under the guidance of the Underwriting Manager. We'll trust you to manage your workload with a sense of urgency around quote deadlines and production targets. You'll partner closely with underwriting management to review more complex cases requiring a higher degree of underwriting authority. 

What  you can expect:

  • Culture of innovation, teamwork, supportive colleagues and leaders willing to invest in talent
  • Internal mobility opportunities 
  • Visibility to senior leaders and partnership with cross functional teams
  • Opportunity to impact change
  • Benefits – competitive compensation, paid time off, comprehensive wellness benefits and programs, employer funded health savings account, profit sharing, 401k, paid parental leave, employee stock purchase plan, tuition assistance and professional continuing education

We'll count on you to:

  • Write and retain profitable stop loss cases adhering to the company’s guidelines and within assigned letter of authority.
  • Establish the basics of medical underwriting by training with and learning from the Company’s internal Clinical Underwriting staff.
  • Properly complete and clearly articulate thought process around risk selection and pricing for efficient reviews with underwriting management and clinical staff.
  • Become acquainted with target production sources as well as BAH Sales and Account Management teams and begin establishing his/her own relationships using effective forms of communication. 
  • Accurately document underwriting thought process and authority reviews through company journal and filing system.

What you need to have:

  • Bachelors’ degree
  • 3+ years of progressive Stop Loss Underwriting experience or equivalent combination of education and experience.
  • A basic understanding of stop loss market dynamics, risk management strategies, and a strong desire to stay ahead of emerging risks in the market.
  • A basic skillset in the areas of math, communication and negotiation, with a strong desire to grow these skillsets under the direction and training of more seasoned staff.
  • Strong time management skills and self-discipline to effectively manage a large case load volume during peak production cycles.
  • Proficiency in Microsoft applications including Word, Excel and Outlook.

What makes you stand out:

  • Experience with David Young / Connexure System 
  • Ability to establish and maintain positive working relationships with all operational areas, management and staff to further the company’s mission
  • Strong consulting and interpersonal skills with an ability to interact with brokers, clients and service vendors.

We do not accept any unsolicited resumes from external recruiting agencies or firms.
The company offers a competitive compensation plan and robust benefits package for full time regular employees which for this role include:
Base Salary Range: $90,000 - $110,000
Eligible to participate in annual discretionary bonus.
Benefits: Health, Dental, Vision, Life, Disability, Wellness, Paid Time Off, 401(k) and Profit-Sharing plans.
The actual salary for this position will be determined by a number of factors, including the scope, complexity and location of the role; the skills, education, training, credentials and experience of the candidate; and other conditions of employment.
Sponsorship not Offered for this Role