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Remote Stop Loss Insurance Jobs in Boston, MA (NOW HIRING)

Account Manager

Lynnfield, MA ยท On-site +1

$95K - $110K/yr

Request and review loss runs. * Handle renewal solicitations. * Review insurance applications ... remote work is an option for the right candidate. * Knowledge of marine policies and industry ...

Account Manager

Lynnfield, MA ยท On-site +1

$95K - $110K/yr

Request and review loss runs. * Handle renewal solicitations. * Review insurance applications ... remote work is an option for the right candidate. * Knowledge of marine policies and industry ...

Showing results 41-60

Remote Stop Loss Insurance information

See Boston, MA salary details

$17

$34

$67

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

As of Sep 3, 2026, the average hourly pay for remote stop loss insurance in Boston, MA is $34.13, according to ZipRecruiter salary data. Most workers in this role earn between $20.91 and $51.44 per hour, depending on experience, location, and employer.

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 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.

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 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 cities near Boston, MA are hiring for Remote Stop Loss Insurance jobs?

Cities near Boston, MA with the most Remote Stop Loss Insurance job openings:

Infographic showing various Remote Stop Loss Insurance job openings in Boston, MA as of August 2026, with employment types broken down into 100% Full Time. Highlights an 100% Remote job distribution, with an average salary of $71,000 per year, or $34.1 per hour.

Senior Underwriter, Structured Solutions - Remote

trisura

Boston, MA โ€ข On-site, Remote

$107K - $126K/yr

Full-time

Medical, Dental, Vision, Retirement

Re-posted 7 days ago


Job description

Atย Trisura, we expect more because we believe it can be done better.

Trisura brings innovative solutions and expertise through a select network of both national and regional brokerage firms in the commercial insurance space.

Trisura is a growth-oriented team with a commitment to attracting and retaining exceptional talent. Our growth has awarded us accolades, and our entrepreneurial style and niche market position ensure that our people see the results of their hard work reflected in the companyโ€™s success.ย  As our organization continues to grow, we are investing in enterprise-wide process maturity, system governance, and delivery excellence to support scalable and compliant operations.

Senior Underwriter โ€“ Structured Solutions

Remote - USA

ย 

Reporting to the Executive Vice President, Structured Solutions, the successful candidate will be a passionate, results-driven underwriter with the experience and vision to grow our Structured Solutions portfolio. Working in close collaboration with our ceded reinsurance, legal, client relations, finance and claims teams, you will evaluate and execute program opportunities from end to end. You will play a key role in developing underwriting guidelines, procedures, and policy language, building rating plans, and providing strategic oversight of a growing book of business.

As an integral member of the team, you will bring:

  • 10+ years of commercial underwriting experience with a focus on multi-line portfolio management.
  • Strong communication, relationship management, organizational and analytical skills, with a demonstrated ability to manage a portfolio of business.
  • Familiarity with rating and policy issuance platforms, with the ability to quickly learn and adapt to proprietary systems.
  • Working knowledge of ISO, admitted and non-admitted product execution.
  • Proven understanding of manuscript and admitted form language, including policy coverage analysis.
  • Demonstrated ability to leverage analytical tools, data reports and underwriting technology.
  • The ability to thrive in a dynamic, fast-paced environment, adapting quickly, collaborating broadly and delivering solutions under pressure.
  • Flexibility, a willingness to learn on the job, and a positive, can-do attitude.
  • A highly motivated, results-oriented mindset with a proven track record as a creative problem solver.
  • Excellent verbal and written communication skills.
  • Willingness to travel approximately 30% of the time.

ย 

Responsibilities include:

  • Preparing underwriting review documents and summaries for presentation to senior management for each assigned program, including plans for new business, renewal rate management, and expected retentions, all designed to position the division to meet its profit objectives.
  • Participating in underwriting reviews and conducting additional file reviews as needed.
  • Leveraging data and analytics to actively manage all programs and drive profitability through consistent monitoring of renewals, rate targets, retentions, trends, and lost business, on a monthly basis.
  • Developing a thorough understanding of each assigned program, including the relevant industries, their loss exposures, and any needed updated to program eligibility and coverage terms, in order to minimize unanticipated adverse exposures.
  • Proactively identify training opportunities at the Program Administrator level to strengthen line-of-business knowledge, and guiding Program Administrators in risk selection, pricing, coverage terms and conditions in alignment with authorities granted by Trisura.
  • Demonstrating a clear understanding of industry changes and their potential impact by line-of-business, and providing well-articulated recommendations during the account referral process.
  • Ensuring Program Administrator meet Trisuraโ€™s underwriting expectations and remain aligned with business plans through active management of underwriting guidelines, file reviews, and client relations meetings.
  • Collaborating with Actuarial, Finance, Claims, Operations, Compliance, Systems, and Legal teams as required.
  • Developing and maintaining strong working relationships with Program Administrators through regular on-site visits, conference calls, and overseeing the onboarding and implementation of new programs.
  • Leading new program opportunity due diligence reviews and overseeing the onboarding and implementation of new programs.
  • Successfully managing the renewal of current program relationships on an annual basis.

If you are looking for a career at an exciting and rewarding company, driven to excel, thriving in a team environment, and eager to contribute to an organization that truly values your input, we want to hear from you!

We thank all candidates for their interest, however, only those selected for an interview will be contacted.

Here at Trisura, we are committed to an inclusive and barrier-free workplace that reflects diversity. Accommodation will be provided on request for candidates taking part in all aspects of our recruitment and selection process.ย  All qualified applications will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identify, national origin, disability or protected veteran status.

The salary range is expected to be $175,000 to $200,000 plus bonus, based on geographical location and experience. Trisura offers a comprehensive benefit package that includes medical, dental, and vision insurance, as well as 401(k) with company match and Employee Stock Purchase Plan.ย 

www.trisura.com