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Contractor Insurance Jobs in Madison, WI (NOW HIRING)

HealthMarkets, Inc.

Insurance Agent

Janesville, WI

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 ...

HealthMarkets, Inc.

Insurance Agent

Madison, WI

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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Contractor Insurance information

See Madison, WI salary details

$37.8K

$83.4K

$123.4K

How much do contractor insurance jobs pay per year?

As of Jun 1, 2026, the average yearly pay for contractor insurance in Madison, WI is $83,429.00, according to ZipRecruiter salary data. Most workers in this role earn between $67,000.00 and $99,800.00 per year, depending on experience, location, and employer.

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

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 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.

Why do most insurance agents quit?

Most insurance agents quit due to high competition, challenging sales targets, and inconsistent income, which can lead to job dissatisfaction. The role often requires strong communication skills, persistence, and self-motivation, and many find the workload and pressure difficult to sustain long-term.

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 are popular job titles related to Contractor Insurance jobs in Madison, WI? For Contractor Insurance jobs in Madison, WI, the most frequently searched job titles are:
What job categories do people searching Contractor Insurance jobs in Madison, WI look for? The top searched job categories for Contractor Insurance jobs in Madison, WI are:
What cities near Madison, WI are hiring for Contractor Insurance jobs? Cities near Madison, WI with the most Contractor Insurance job openings:
Contractor Insurance jobs near you
Licensed Insurance Agent

Licensed Insurance Agent

HealthMarkets Insurance Agency

Janesville, WI • Remote

$50K - $120K/yr

Contractor

Posted 13 days ago

Job description

HealthMarkets Overview Job Description:

If you’re looking for an exciting opportunity where you can change people’s lives and achieve financial success as an independent licensed insurance agent, you’ve come to the right place. Becoming an independent licensed insurance agent with HealthMarkets is an opportunity unlike any other. HealthMarkets offers licensed insurance agents the resources and support they need to grow their businesses and succeed in the industry, all while making a difference in people’s lives.

And who are we? HealthMarkets is a technology-enabled health insurance agency delivering high-touch, customized health and supplemental insurance solutions to individuals, families and small businesses. Millions of Americans depend on us to help explore their insurance coverage options – and we’re looking for licensed insurance agents like you to help us continue that mission.

So, whether you’re an experienced insurance agent looking for your next opportunity or are just starting out and looking for an opportunity to demonstrate your talents, HealthMarkets is the career move that can help change your life.

Job description:

If you’re a licensed insurance agent with 4-5 years of experience, we want you. As an independently contracted licensed insurance agent with HealthMarkets, you’ll be collaborating with one of the largest independent health insurance agencies in the US. You’ll have the opportunity to grow a business, all while making a difference in people’s lives.

Not only that, but HealthMarkets will offer you the resources you need to succeed. We’ll give you access to leads, quoting tools, training resources, and more so you can focus on what you do best: selling. Contact us today and succeed on your terms with HealthMarkets.

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.

51934-HM-0225

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.