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Stop Loss Insurance Jobs (NOW HIRING)

Jencap

Senior Underwriter - Medical Stop Loss

Danvers, MA · On-site +1

$104K - $123K/yr

About the Company: Aran Insurance Underwriters is a leading provider of innovative insurance ... The Senior Underwriter - Medical Stop Loss is responsible for the evaluation, risk assessment ...

Jencap

Senior Underwriter - Medical Stop Loss

Avon, CT · On-site

$96K - $114K/yr

About the Company: Aran Insurance Underwriters is a leading provider of innovative insurance ... The Senior Underwriter - Medical Stop Loss is responsible for the evaluation, risk assessment ...

Lucent Health Solutions LLC

Stop Loss Manager

Nashville, TN · On-site

$138K/yr

This approach helps self-insured employers provide care management that enables health plan participants to make smarter, cost-saving healthcare decisions. Continuous data analytics offer ongoing ...

Captive Resources

Underwriter

Itasca, IL

$100K - $135K/hr

The Underwriter is responsible for evaluating and underwriting stop-loss insurance. The role involves analyzing medical risk, pricing policies, and making recommendations based on a thorough ...

Captive Resources

Underwriter

Itasca, IL · On-site

$100K - $135K/hr

The Underwriter is responsible for evaluating and underwriting stop-loss insurance. The role involves analyzing medical risk, pricing policies, and making recommendations based on a thorough ...

Captive Resources

Underwriter

Itasca, IL · On-site +1

The Underwriter is responsible for evaluating and underwriting stop-loss insurance. The role involves analyzing medical risk, pricing policies, and making recommendations based on a thorough ...

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Stop Loss Insurance information

What are the key skills and qualifications needed to thrive in the Stop Loss Insurance position, and why are they important?

To excel in Stop Loss Insurance, professionals need a solid understanding of underwriting principles, risk assessment, healthcare plan structures, and industry regulations, often supported by a bachelor’s degree in business, finance, or healthcare management. Familiarity with actuarial software, claims management systems, and relevant insurance certifications such as the Health Insurance Associate (HIA) or Certified Employee Benefit Specialist (CEBS) is highly valued. Strong analytical thinking, attention to detail, and effective communication skills help individuals liaise with clients, brokers, and internal stakeholders. These abilities ensure accurate risk evaluation, foster positive client relationships, and enable informed decision-making in a fast-paced, detail-oriented industry.

What is a Stop Loss Insurance job?

A Stop Loss Insurance job typically involves managing and underwriting stop-loss policies, which protect self-funded employers from catastrophic claims. Professionals in this role assess risk, analyze claims data, and work with brokers or insurers to structure policies that limit financial exposure. They may also negotiate contract terms, monitor ongoing claims, and ensure compliance with healthcare regulations.

What are typical daily responsibilities for a professional working in Stop Loss Insurance?

A typical day in a Stop Loss Insurance role involves reviewing and underwriting group health risk data, analyzing claims activity, and issuing or renewing policies based on risk evaluation criteria. Professionals also interact with brokers, third-party administrators, and employer clients to clarify coverage terms, answer questions, and negotiate contract specifics. Additional tasks may include monitoring large claims, coordinating with actuarial teams, and staying current with regulations and market trends. This dynamic environment requires effective prioritization and strong collaboration, ensuring accurate coverage while supporting clients’ risk management needs.

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What cities are hiring for Stop Loss Insurance jobs? Cities with the most Stop Loss Insurance job openings:
What are the most commonly searched types of Stop Loss Insurance jobs? The most popular types of Stop Loss Insurance jobs are:
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Stop Loss Insurance jobs near you
Infographic showing various Stop Loss Insurance job openings in the United States as of June 2026, with employment types broken down into 4% As Needed, 29% Full Time, 16% Part Time, and 51% Contract. Highlights an 97% Physical, 1% Hybrid, and 2% Remote job distribution.
Senior Underwriter - Medical Stop Loss

Senior Underwriter - Medical Stop Loss

Jencap

Danvers, MA • On-site, Remote

$104K - $123K/yr

Full-time

Medical, Retirement

Posted 17 days ago

Job description

Why Jencap? We are one of the largest wholesale insurance intermediaries in the United States with expertise in wholesale brokerage, binding authority, and program management. The common thread woven throughout our success story is our collaborative and driven team of people. Our teams are empowered and work together to find solutions. We have a passion culture – with teamwork, collaboration and a focus on growing individuals and giving them the tools & development opportunities to have a successful career.

About the Company:

Aran Insurance Underwriters is a leading provider of innovative insurance solutions for self-funded employers and their partners. We are committed to delivering exceptional value, service, and expertise to our clients. As part of our ongoing growth, we are seeking a highly experienced Senior Underwriter specializing in stop loss insurance to join our dynamic team.

The Senior Underwriter – Medical Stop Loss is responsible for the evaluation, risk assessment, pricing, and underwriting of stop loss insurance for self‑funded employer groups. The ideal candidate brings strong stop loss market expertise, sound analytical judgment, and the ability to develop trusted relationships with brokers, consultants, TPAs, and internal stakeholders.

This role is ideally suited for candidates located in the Phoenix, AZ area working remotely; however, highly qualified candidates located elsewhere in the U.S. will be considered for a fully remote arrangement.

Key Responsibilities:

  • Underwrite new and renewal stop loss business in accordance with underwriting guidelines, risk appetite, and profitability targets
  • Analyze complex self‑funded employer group data, including claims experience, demographics, plan design, and funding structures
  • Partner closely with the Chief Underwriting Officer to develop customized underwriting and pricing solutions
  • Establish and maintain strong relationships with brokers, consultants, TPAs, and clients; participate in finalist presentations and renewal discussions as needed
  • Monitor portfolio performance and support profitable growth initiatives
  • Contribute to underwriting process improvements, product enhancements, and best‑practice initiatives

Qualifications:

  • Bachelor's degree in business, finance, actuarial science, or a related field required; advanced degree or professional designations (e.g., CEBS, FLMI, ASA) preferred
  • 5–10 years of experience underwriting stop loss insurance for self‑funded employer groups
  • Strong knowledge of stop loss insurance products, market dynamics, and regulatory requirements
  • Proven ability to make sound risk decisions and contribute to profitable portfolio performance
  • Excellent analytical, quantitative, and problem‑solving skills
  • Strong relationship‑building, negotiation, and communication abilities
  • Proficiency in underwriting systems, analytics tools, and Microsoft Office Suite
  • Ability to work independently while collaborating effectively in a fast‑paced, growth‑oriented environment

The base salary offered for the successful candidate will be based on compensable factors such as job-relevant education, job-relevant experience, training, licensure, demonstrated competencies, geographic location, and other factors. Discretionary incentive compensation may be awarded. Jencap also offers a range of benefits and programs, based on eligibility, which currently include but are not limited to; comprehensive health care coverage, a 401k plan, and tuition reimbursement. Jencap is an emerging and rapidly growing leader in the industry and as such, we approach talent acquisition as an opportunity to identify the best talent. Therefore, the level of the role and compensation may vary depending upon the best available candidate.

Want the opportunity to build something new? Expand your knowledge and stretch your experience through new and emerging risks? Have your voice heard, your skills properly applied, and to add tangible value to an organization? You're in the right place.

Jencap is dynamic, bold, tenacious, and trusted in the industry. Here, you are not just one of the many, you are one of us. We truly are better together.

Jencap is an Equal Opportunity Employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, age, national origin or citizenship status, sexual orientation, gender identity or expression, pregnancy, marital or familial status, disability status, medical condition, genetic information, military or veteran status, political affiliation, or any other characteristic protected by law. We are committed to fostering a work community where every colleague feels welcomed, valued, respected and heard, as we believe that that creating an environment where every employee feels included and empowered, helps us to deliver the best outcome to our clients.