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Contractor Insurance Jobs in Milwaukee, WI (NOW HIRING)

HealthMarkets, Inc.

Insurance Agent

Milwaukee, WI · On-site

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 Milwaukee, WI

Contractor Insurance information

See Milwaukee, WI salary details

$36.9K

$81.6K

$120.7K

How much do contractor insurance jobs pay per year?

As of Jul 15, 2026, the average yearly pay for contractor insurance in Milwaukee, WI is $81,576.00, according to ZipRecruiter salary data. Most workers in this role earn between $65,500.00 and $97,500.00 per year, depending on experience, location, and employer.

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 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 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 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 popular job titles related to Contractor Insurance jobs in Milwaukee, WI? For Contractor Insurance jobs in Milwaukee, WI, the most frequently searched job titles are:
What job categories do people searching Contractor Insurance jobs in Milwaukee, WI look for? The top searched job categories for Contractor Insurance jobs in Milwaukee, WI are:
What cities near Milwaukee, WI are hiring for Contractor Insurance jobs? Cities near Milwaukee, WI with the most Contractor Insurance job openings:
Contractor Insurance jobs near you
Infographic showing various Contractor Insurance job openings in Milwaukee, WI as of July 2026, with employment types broken down into 25% Full Time, and 75% Contract. Highlights an 75% In-person, and 25% Remote job distribution, with an average salary of $81,576 per year, or $39.2 per hour.
Independent Contractor - Landscaping

Independent Contractor - Landscaping

City Wide Facility Solutions

Milwaukee, WI • On-site

Contractor

Re-posted 9 days ago

Job description

City Wide Facility Solutions is the largest management company in the building maintenance industry, facilitating janitorial and more than 20 additional maintenance services for every client. But we do more than manage maintenance services for commercial facilities - we pride ourselves on being a partner that helps save time and solve problems!

We are currently looking for Janitorial Independent Contractors to partner with to help fulfill the needs of our clients. City Wide can help your business grow, focus on the work, not on selling and collecting on the accounts, and most importantly, increase your income.

If you are interested in joining the City Wide Network as an independent contractor who provides landscaping services - please apply to this posting.

Requirements

INDEPENDENT CONTRACTORS MUST PROVIDE THE FOLLOWING:

  • Valid Business License, LLC or Inc
  • Worker's Compensation Insurance
  • General Liability Insurance and Non Owned Auto
  • Federal EIN #
  • Verifiable references
  • 18 years of age minimum
  • You can not be a sole proprietor

Benefits

This is for a contract opportunity and is not benefit eligible.

Apply