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Remote 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 ... S. will be considered for a fully remote arrangement . Key Responsibilities: * Underwrite new and ...

Allied

Stop Loss Claims Specialist II-Specific

Chicago, IL · On-site +1

$24 - $26/hr

Remote Here at Allied, we believe that great talent can thrive from anywhere. Our remote friendly ... Insurance, Generous Paid Time Off, Tuition Reimbursement, EAP, and a Technology Stipend. Allied ...

Allied

Stop Loss Claims Specialist I-Specific

Chicago, IL · On-site +1

$23 - $24/hr

Remote Here at Allied, we believe that great talent can thrive from anywhere. Our remote friendly ... Insurance, Generous Paid Time Off, Tuition Reimbursement, EAP, and a Technology Stipend. Allied ...

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 ...

Allied

Stop Loss Claims Specialist I-Aggregate

Chicago, IL · On-site +1

$23 - $24/hr

Remote Here at Allied, we believe that great talent can thrive from anywhere. Our remote friendly ... Insurance, Generous Paid Time Off, Tuition Reimbursement, EAP, and a Technology Stipend. Allied ...

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Remote Stop Loss Insurance information

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$15

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How much do remote stop loss insurance jobs pay per hour?

As of Jun 19, 2026, the average hourly pay for remote stop loss insurance in the United States is $31.42, according to ZipRecruiter salary data. Most workers in this role earn between $19.23 and $47.36 per hour, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as a Remote Stop Loss Insurance Specialist, and why are they important?

To excel as a Remote Stop Loss Insurance Specialist, you need expertise in health insurance underwriting, risk assessment, and policy analysis, often supported by a background in insurance or finance. Familiarity with industry-standard claims management systems, CRM platforms, and regulatory compliance tools is essential. Strong analytical thinking, attention to detail, and effective written communication are crucial soft skills for success in a remote environment. These abilities ensure accurate risk evaluation, regulatory adherence, and clear client interactions, which are critical for managing high-value stop loss insurance contracts.

What is remote stop loss insurance?

Remote stop loss insurance is a type of coverage designed to protect self-funded employers from large or catastrophic claims, but managed and administered through digital or remote platforms. This insurance reimburses employers for claims that exceed a predetermined limit, helping them manage risk and avoid significant financial loss. The 'remote' aspect refers to the use of online tools and services for policy management, claims processing, and communication, allowing for flexible and efficient administration without the need for in-person meetings. This is particularly beneficial for companies with distributed teams or those seeking streamlined, technology-driven solutions.

What is the difference between Remote Stop Loss Insurance vs Remote Underwriter?

AspectRemote Stop Loss InsuranceRemote Underwriter
CredentialsInsurance licenses, actuarial knowledgeInsurance licenses, underwriting certifications
Work EnvironmentInsurance companies, brokers, remoteInsurance companies, remote or office
Industry UsageHealth and self-funded plansInsurance policy assessment and risk evaluation

Remote Stop Loss Insurance professionals focus on providing coverage for self-funded health plans, managing risk, and setting policy terms. Remote Underwriters evaluate insurance applications, assess risks, and determine policy eligibility. While both roles require insurance knowledge and licenses, Stop Loss Insurance specialists concentrate on risk management for health plans, whereas Underwriters focus on evaluating individual applications. Understanding these differences helps clarify career paths and job expectations in the insurance industry.

What are some common challenges faced by professionals working in remote stop loss insurance roles?

One common challenge in remote stop loss insurance roles is maintaining clear and effective communication with underwriters, brokers, and clients, since much of the collaboration happens virtually. Additionally, staying updated on changing regulations and market trends requires proactive self-learning and digital resourcefulness. Managing sensitive data securely and ensuring timely turnaround on complex claims or policy analysis can also be demanding when working remotely. Building strong relationships with team members and clients, despite the lack of in-person interaction, is key to long-term success in this field.
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Remote Stop Loss Insurance jobs near you
Senior Underwriter - Medical Stop Loss

Senior Underwriter - Medical Stop Loss

Jencap

Danvers, MA • On-site, Remote

$104K - $123K/yr

Full-time

Medical, Retirement

Posted 5 days ago

Be an early applicant

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.