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Remote Stop Loss Insurance Jobs in Oregon (NOW HIRING)

Principal Actuary

OR ยท On-site +1

$220K - $270K/yr

This role is preferred in Tampa, FL, with hybrid flexibility, but remote is an option for the right ... Work with employers, brokers, consultants, TPAs, and stop-loss partners on plan design questions ...

Account Manager

OR ยท On-site +1

... TPA, insurance, or employee benefits industry * Proven experience engaging and building relationships with C-suite executives * Strong knowledge of self-funded health plans including stop loss ...

Charles Taylor is a highly successful global provider of professional services to the insurance ... Receives newly reported claims which include loss time, litigated and medical only * Maintains and ...

Posted today

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Remote Stop Loss Insurance information

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 are the most commonly searched types of Stop Loss Insurance jobs in Oregon?

The most popular types of Stop Loss Insurance jobs in Oregon are:

What are popular job titles related to Remote Stop Loss Insurance jobs in Oregon?

For Remote Stop Loss Insurance jobs in Oregon, the most frequently searched job titles are:

What cities in Oregon are hiring for Remote Stop Loss Insurance jobs?

Cities in Oregon with the most Remote Stop Loss Insurance job openings:

Infographic showing various Remote Stop Loss Insurance job openings in Oregon as of August 2026, with employment types broken down into 1% As Needed, 74% Full Time, 19% Part Time, and 6% Contract. Highlights an 91% Physical, 1% Hybrid, and 8% Remote job distribution.

Principal Actuary

HealthJoy

OR โ€ข On-site, Remote

$220K - $270K/yr

Full-time

Posted 8 days ago


Job description

This role is preferred in Tampa, FL, with hybrid flexibility, but remote is an option for the right person.Come for the mission. Stay for the innovation.

Let's keep things simple: we are an unbelievably talented, hard-working, and compassionate team driving towards a mission that impacts every single one of us - even you.

Healthcare benefits are complex and largely underutilized by most people. That's why HealthJoy was built with one vision: to remove the complexity from being healthy and well. We do that by guiding employees to affordable, high-quality healthcare, consolidating our clients' health and wellness strategies into the HealthJoy Benefits Operating System - a simple, unified digital experience. The result: healthier employees and a healthier bottom line.

HealthJoy is at the forefront of using AI to transform the healthcare benefits industry. We're building intelligent platforms that use predictive analytics, natural language processing, and machine learning to guide employees to affordable, high-quality care. Our team is passionate about creating a more equitable and understandable benefits experience, while saving our clients time and money.

HealthJoy has garnered workplace awards from Inc.'s Fastest Growing Startups and Built In Chicago's Best Places to Work while growing globally to over 300 team members. We're continuing down the path of high growth and high impact - and this role is one of the most consequential bets we're making.

ย Your Impact.

We are hiring a Principal Actuary to lead the actuarial side of how we design, price, and measure our products. You will report directly to the CFO and work closely with our executive, product, and data science teams. We already have strong data science and analytics capabilities; this role adds dedicated actuarial leadership to that work.

Some of what this role will work on is not public yet. We will share the specifics during the interview process. What we can say here is that the work sits at the center of where the company is headed, and the math has to be good enough to convince skeptical outside reviewers.

Own how we measure value. Build and defend the methodology we use to measure the financial results of our programs. It needs to hold up when an outside actuary, a benefits consultant, or an underwriter takes it apart.

Build risk and forecasting models. Partner with our data science team on models that forecast medical cost and utilization for self-funded populations, and own the actuarial assumptions behind them.

Design Health Reimbursement Arrangements. Design employer-funded HRAs and incentive programs, including funding levels, rollover rules, reimbursement and substantiation, keeping members HSA-eligible, and staying compliant with IRS rules, including Section 105(h) nondiscrimination testing.

Support pricing. Help structure our pricing, including performance guarantees, reconciliation mechanics, and the reserves behind them.

Support plan design. Work with employers, brokers, consultants, TPAs, and stop-loss partners on plan design questions across our book of business.

Stand behind the numbers. You will sit across the table from actuaries at consulting firms and underwriting partners. You will explain our methods and answer the hard questions.

Your Experience.
  • ย  ย  ASA or FSA (MAAA preferred) with at least 7+ years of health actuarial experience, ideally on commercial or employer-sponsored plans
  • ย  ย  A strong understanding of self-funded plan economics, including stop-loss, lasering, and claims forecasting
  • ย  ย  Hands-on experience designing and modeling employer-funded Health Reimbursement Arrangements, including how they fit with the medical plan, HSA compatibility, ERISA and COBRA requirements, and IRS compliance
  • ย  ย  Experience forecasting HRA utilization, setting rollover and forfeiture assumptions, and pricing incentive dollars based on how members actually respond
  • ย  ย  Experience building or reviewing program savings studies, and honest opinions about where the common methods fall short
  • ย  ย  Strong SQL skills; Python or R is a plus
  • ย  ย  A track record of standing behind numbers that were reviewed by outside parties
You might be a fit if:
  • ย  ย  You have built savings or value studies and been frustrated by what you could not prove
  • ย  ย  You would rather work at a company that sets its measurement standards up front than one that leads with a flashy ROI slide
  • ย  ย  You want broad ownership and visibility rather than a narrow slice of a large actuarial department
  • ย  ย  You want a direct line to the executive team and a real say in product, pricing, and partner decisions
Total Rewards

Job band - 90 - this is a senior leadership role, reporting directly to the CFO

Base salary of $220,000 to $270,000, plus an annual bonus target and equity. The final offer depends on experience and credentials.

Certain roles are eligible for additional cash incentives such as commission, annual bonus targets, overtime pay or other variable incentives.

HealthJoy maintains a comprehensive strategy to determine rewarding and competitive packages for individual compensation for new hires, internal promotions and internal job changes. This strategy is based on several factors unique to each individual, including: 1) the skills, experience and qualifications of the individual; 2) the responsibilities and demands of the role; 3) analysis of external market data; and 4) company budget and financial performance.