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Contractor Insurance Jobs in Estero, FL (NOW HIRING)

HealthMarkets, Inc.

Insurance Agent

Cape Coral, FL

As an independent contractor licensed insurance agent with HealthMarkets, youll be collaborating with one of the largest independent health insurance agencies in the US. Youll have the opportunity to ...

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All JobsContractor Insurance JobsContractor Insurance Jobs in Estero, FL

Contractor Insurance information

See Estero, FL salary details

$35.7K

$78.9K

$116.7K

How much do contractor insurance jobs pay per year?

As of Aug 24, 2026, the average yearly pay for contractor insurance in Estero, FL is $78,860.00, according to ZipRecruiter salary data. Most workers in this role earn between $63,300.00 and $94,300.00 per year, depending on experience, location, and employer.

What is contractor insurance?

Contractor insurance is a type of business insurance designed to protect contractors and construction professionals from financial losses related to their work. It typically covers risks such as property damage, bodily injury to third parties, and legal costs arising from accidents or mistakes on the job. Common types of contractor insurance include general liability, workers’ compensation, and tools and equipment coverage. Having the right insurance helps ensure contractors meet legal requirements and client expectations, and provides peace of mind while working on projects.

What are the key skills and qualifications needed to thrive as a contractor insurance specialist?

To thrive as a Contractor Insurance Specialist, you need a solid understanding of insurance products, risk assessment, and relevant legal regulations, typically supported by a state insurance license. Familiarity with insurance management software, quoting systems, and CRM platforms is essential for efficiency and accuracy. Strong interpersonal, negotiation, and problem-solving skills help build client trust and tailor solutions to unique contractor needs. These competencies are crucial for ensuring clients have appropriate coverage, mitigating risk, and maintaining a competitive edge in the insurance industry.

What are some common challenges faced by professionals working in contractor insurance, and how can they be addressed?

Professionals in contractor insurance often navigate challenges such as keeping up with changing regulations, accurately assessing risk for a diverse range of contracting businesses, and clearly communicating policy details to clients who may be unfamiliar with insurance terminology. Staying updated through ongoing education and industry resources, collaborating closely with underwriters and risk assessors, and developing strong client communication skills can help address these challenges. Teamwork within the agency and regular training sessions also play a crucial role in effectively managing client expectations and ensuring compliance.

What is the difference between Contractor Insurance vs Subcontractor Insurance?

AspectContractor InsuranceSubcontractor Insurance
Required CredentialsGeneral liability, workers' compensation, commercial autoSimilar credentials, often with specialized coverage for subcontracted work
Work EnvironmentMain contractor overseeing projectsPerforming specific tasks under a contractor
Employer & Industry UsageUsed by general contractors and construction firmsUsed by subcontractors and specialty trade workers
Comparison Search IntentUnderstanding coverage differences for contractorsUnderstanding coverage for subcontracted work

Contractor Insurance covers general contractors managing entire projects, while Subcontractor Insurance is tailored for subcontractors performing specialized tasks. Both require similar credentials but serve different roles in the construction industry. Understanding these differences helps ensure proper coverage and risk management for each party involved.

What does contractor insurance do?

Contractor insurance provides coverage for contractors against risks such as property damage, liability claims, and worker injuries. It helps protect their business assets and ensures compliance with legal requirements, often including general liability and workers' compensation policies.

What cities near Estero, FL are hiring for Contractor Insurance jobs?

Cities near Estero, FL with the most Contractor Insurance job openings:

Contractor Insurance jobs near you
Infographic showing various Contractor Insurance job openings in Estero, FL as of August 2026, with employment types broken down into 1% As Needed, 70% Full Time, 24% Part Time, and 5% Contract. Highlights an 88% Physical, 1% Hybrid, and 11% Remote job distribution, with an average salary of $78,860 per year, or $37.9 per hour.

Licensed Insurance Professional

HealthMarkets Insurance Agency

Cape Coral, FL • Remote

$50K - $120K/yr

Contractor

Re-posted 19 days ago

Job description

A Career for Driven, Self-starting Insurance Professionals


A career with HealthMarkets is built for insurance professionals who take ownership,
drive results, and want to build something of their own.
How you build your career with HealthMarkets


Help individuals, families, and seniors make confident insurance decisions through a
consultative approach. You’ll guide clients to coverage that fits their needs and budget
across a wide product portfolio, including:


 Individual family health insurance
 Medicare Advantage Medicare Supplement plans
 Supplemental products (dental, vision, accident, critical illness)
 Life insurance


Having access to HealthMarkets’ tools and carrier partnerships, you’ll educate, compare
plans, and support clients through enrollment and beyond.


How do you thrive with HealthMarkets
 Self-motivated and confident
 Consultative, not transactional
 Accountable for results
 Think and operate like a business owner
 Value independence
 Understand that sales rewards effort and discipline


What HealthMarkets Offers


 Qualified lead options for steady pipeline growth
 Advanced quoting and enrollment technology
 Comprehensive training and ongoing development
 Strong carrier relationships and operational support
 A scalable infrastructure that preserves your independence


As an independent licensed insurance agent, you’ll collaborate with one of the largest
independent health insurance agencies in the U.S. while maintaining control of how you
run your business.


You’re in charge of your future. We help you build it.

Disclaimer: Licensed Insurance Agents with HealthMarkets Insurance Agency are self-employed
acting as independent contractors and not as employees. HealthMarkets independent licensed
insurance agents shall for all purposes be deemed to be independent contractors and shall have
no authority to act or represent themselves as an employee or partner of HealthMarkets
Insurance Agency. An Independent licensed insurance agent with HealthMarkets is a
commission only opportunity. HealthMarkets Insurance Agency, Inc., is licensed as an insurance
agency nationwide except in MA. Not all agents are licensed to sell all products. Service and
product availability may vary by state.
53152-HM-0426

Company Description

Expect to have both a life and a career with HealthMarkets. When you join us as a Licensed Independent Insurance Agent, you'll be building a business that you control with our support. So, you can head out for a run, be there for your kid's soccer matches – even chase tornadoes if that's your thing. Start succeeding on your terms.

HealthMarkets is a technology-enabled health insurance marketplace that delivers high-touch, customized health and supplemental insurance solutions. Our Licensed Independent Insurance Agents serve our customers by helping families, individuals, and small businesses find the coverage they need at a price they can afford.