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Entry Level Stop Loss Insurance Jobs (NOW HIRING)

Operations Analyst

Hartford, CT · Hybrid

$49K - $66K/yr

Broad knowledge of Stop Loss Insurance products and processes, preferred * Ability to think creatively to resolve the more complex or non-routine issues * Strong written and verbal communication ...

Operations Analyst

Portland, ME · Hybrid

$49K - $66K/yr

Broad knowledge of Stop Loss Insurance products and processes, preferred * Ability to think creatively to resolve the more complex or non-routine issues * Strong written and verbal communication ...

Operations Analyst

Baltimore, MD · Hybrid

$49K - $66K/yr

Broad knowledge of Stop Loss Insurance products and processes, preferred * Ability to think creatively to resolve the more complex or non-routine issues * Strong written and verbal communication ...

Operations Analyst

Portland, ME · Hybrid

$49K - $66K/yr

Broad knowledge of Stop Loss Insurance products and processes, preferred * Ability to think creatively to resolve the more complex or non-routine issues * Strong written and verbal communication ...

Underwriting Analyst

Minnetonka, MN · Hybrid

$53K - $79K/yr

Medical Stop Loss provides an added layer of insurance protection to employers who choose to self-fund their health benefit plans. Self-funding can incur risks from catastrophic claims, and Medical ...

Operations Analyst

Wellesley, MA · Hybrid

$49K - $66K/yr

Broad knowledge of Stop Loss Insurance products and processes, preferred * Ability to think creatively to resolve the more complex or non-routine issues * Strong written and verbal communication ...

Operations Analyst

Wellesley, MA · Hybrid

$49K - $66K/yr

Broad knowledge of Stop Loss Insurance products and processes, preferred * Ability to think creatively to resolve the more complex or non-routine issues * Strong written and verbal communication ...

Operations Analyst

Kansas City, KS · Hybrid

$49K - $66K/yr

Broad knowledge of Stop Loss Insurance products and processes, preferred * Ability to think creatively to resolve the more complex or non-routine issues * Strong written and verbal communication ...

Operations Analyst

Baltimore, MD · Hybrid

$49K - $66K/yr

Broad knowledge of Stop Loss Insurance products and processes, preferred * Ability to think creatively to resolve the more complex or non-routine issues * Strong written and verbal communication ...

Operations Analyst

Hartford, CT · Hybrid

$49K - $66K/yr

Broad knowledge of Stop Loss Insurance products and processes, preferred * Ability to think creatively to resolve the more complex or non-routine issues * Strong written and verbal communication ...

Operations Analyst

Milwaukee, WI · Hybrid

$49K - $66K/yr

Broad knowledge of Stop Loss Insurance products and processes, preferred * Ability to think creatively to resolve the more complex or non-routine issues * Strong written and verbal communication ...

Operations Analyst

Wellesley, MA · On-site

$49K - $66K/yr

Broad knowledge of Stop Loss Insurance products and processes, preferred * Ability to think creatively to resolve the more complex or non-routine issues * Strong written and verbal communication ...

Operations Analyst

Kansas City, KS · Hybrid

$49K - $66K/yr

Broad knowledge of Stop Loss Insurance products and processes, preferred * Ability to think creatively to resolve the more complex or non-routine issues * Strong written and verbal communication ...

Operations Analyst

Milwaukee, WI · Hybrid

$49K - $66K/yr

Broad knowledge of Stop Loss Insurance products and processes, preferred * Ability to think creatively to resolve the more complex or non-routine issues * Strong written and verbal communication ...

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Showing results 1-20

Entry Level Stop Loss Insurance information

What are entry level positions in insurance?

Entry level positions in insurance include roles such as insurance assistant, claims processor, underwriter trainee, or customer service representative. These roles typically require minimal experience, focus on learning industry processes, and may involve on-the-job training or certifications like licensing exams for specific insurance types.

What jobs pay 4000 a week without a degree?

Entry-level stop loss insurance roles typically do not pay $4,000 per week without experience or specialized skills. High-paying jobs that can reach this level without a degree often include sales positions, real estate agents, or certain entrepreneurial ventures, but these usually require strong sales skills, certifications, or business acumen. Most roles with such earnings involve commission-based pay or performance incentives rather than fixed salaries for entry-level positions.

What is the highest paying insurance agent job?

The highest paying insurance agent roles are typically senior or specialized positions such as captive agents, insurance brokers, or those working in high-net-worth client segments, with earnings often exceeding $100,000 annually including commissions and bonuses. Success in these roles depends on experience, sales skills, and certifications like the Chartered Property Casualty Underwriter (CPCU).

What is the difference between Entry Level Stop Loss Insurance vs Entry Level Health Insurance Agent?

AspectEntry Level Stop Loss InsuranceEntry Level Health Insurance Agent
Required CredentialsNone or insurance licensingInsurance license, possibly certification
Work EnvironmentInsurance companies, brokers, or consulting firmsInsurance agencies, brokerages, or direct sales
Industry UsageHealth insurance, employer-sponsored plansHealth insurance sales and client consultation

Entry Level Stop Loss Insurance involves understanding health plan cost management, while Entry Level Health Insurance Agents focus on selling and advising clients on health plans. Both roles require insurance licensing and operate within the health insurance industry, but their core functions differ: one manages risk, the other sells coverage.

How to become a stop loss underwriter?

To become a stop loss underwriter, candidates typically need a bachelor's degree in finance, insurance, or a related field. Gaining experience in insurance underwriting, developing strong analytical skills, and understanding healthcare or insurance policies are essential. Professional certifications such as the Chartered Property Casualty Underwriter (CPCU) can enhance prospects in this role.
More about Entry Level Stop Loss Insurance jobs
What are the most commonly searched types of Stop Loss Insurance jobs? The most popular types of Stop Loss Insurance jobs are:
What job categories do people searching Entry Level Stop Loss Insurance jobs look for? The top searched job categories for Entry Level Stop Loss Insurance jobs are:
Infographic showing various Entry Level Stop Loss Insurance job openings in the United States as of July 2026, with employment types broken down into 1% Locum Tenens, 86% Full Time, 12% Part Time, and 1% Contract. Highlights an 96% Physical, 1% Hybrid, and 3% Remote job distribution.

Residential Maintenance & Compliance Inspector

Stop Loss LLC

Alexandria, VA

$23 - $28/hr

Full-time

Medical, PTO

Re-posted 13 days ago


Job description


$23–$28 per hour + Performance Bonuses
Full-Time | Benefits | Take-Home Vehicle | Company Phone | Tools & Equipment Provided
Independent Field Role | High Accountability | Real Impact
Stop Loss, LLC is seeking a high-performing Residential Maintenance & Compliance Inspector
to join our growing field operations team.
This is not an entry-level route position. We are looking for professionals who can manage their
day independently, operate efficiently, communicate clearly, and represent our company with
confidence inside occupied rental properties.
You will serve as a trusted field partner to property managers — ensuring smoke alarm
compliance and conducting structured preventative maintenance surveys that protect rental assets
and reduce risk.
If you take pride in precision, productivity, and professionalism, this role offers both stability and
opportunity.
Compensation &  Benefits
  • $23–$28 per hour based on experience and performance
  • Performance-based bonuses tied to efficiency and quality
  • Take-home company vehicle
  • Company-provided work phone
  • All tools and equipment provided
  • Health insurance
  • Paid time off
  • Full-time, year-round work
We equip our team for success and reward strong execution.
What You’ll Be Responsible For
You will manage an assigned territory and complete scheduled residential inspections with
minimal oversight.
Core responsibilities include:
  • Conduct smoke alarm and carbon monoxide compliance inspections
  • Perform structured preventative maintenance surveys in rental properties
  • Identify, document, and photograph maintenance concerns with clear electronic reporting
  • Install and replace smoke alarms and related safety devices
  • Maintain organized vehicle inventory and accurate product counts
  • Communicate professionally with tenants and property managers
  • Complete routes on schedule while maintaining quality standards
This role requires balancing speed, accuracy, customer service, and mechanical capability.
Top performers in this role are efficient, organized, and solutions oriented.
What We Expect from High-Level Candidates
  • Proven ability to work independently without constant supervision
  • Strong time management and route efficiency
  • High attention to detail in documentation and reporting
  • Comfortable interacting with tenants in occupied homes
  • Experience using mobile reporting tools and digital platforms
  • Mechanical aptitude and confidence using hand and power tools
  • Professional appearance and communication
  • Valid driver’s license with a clean driving record
Preferred Experience:
  • Residential maintenance
  • Field service or inspection
  • Property management support roles
  • Working in occupied residential environments

Physical Requirements
This is an active field position that requires:
  • Ladder work and overhead installations
  • Bending, crawling, squatting, and reaching
  • Lifting and carrying up to 75 pounds
  • Frequent driving between properties

Who Thrives Here?
  • Self-starters
  • Structured, process-driven professionals
  • Individuals who take ownership of their performance
  • Field professionals looking for long-term stability with growth potential
If you’re ready to bring discipline, efficiency, and professionalism to a company that values
performance — apply today.
Stop Loss, LLC is an Equal Opportunity Employer. We are committed to building a diverse and
inclusive team.
About Stop Loss, LLC
Founded in Richmond, Virginia, Stop Loss partners with property managers to provide structured
smoke alarm compliance and preventative maintenance surveys across rental portfolios.
Our work helps protect property investments, reduce operational risk, and give property
managers back valuable time through reliable field execution.
We are a growing company focused on accountability, professionalism, and operational
excellence.