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Contractor Insurance Jobs in Northbrook, IL (NOW HIRING)

HealthMarkets, Inc.

Insurance Agent

Waukegan, IL

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

Elgin, IL

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

Schaumburg, IL

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

Chicago, IL

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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Showing results 1-20

All JobsContractor Insurance JobsContractor Insurance Jobs in Northbrook, IL

Contractor Insurance information

See Northbrook, IL salary details

$38.1K

$84K

$124.3K

How much do contractor insurance jobs pay per year?

As of Aug 22, 2026, the average yearly pay for contractor insurance in Northbrook, IL is $84,039.00, according to ZipRecruiter salary data. Most workers in this role earn between $67,500.00 and $100,500.00 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 job categories do people searching Contractor Insurance jobs in Northbrook, IL look for?

The top searched job categories for Contractor Insurance jobs in Northbrook, IL are:

What cities near Northbrook, IL are hiring for Contractor Insurance jobs?

Cities near Northbrook, IL with the most Contractor Insurance job openings:

Contractor Insurance jobs near you
Infographic showing various Contractor Insurance job openings in Northbrook, IL as of August 2026, with employment types broken down into 1% As Needed, 66% Full Time, 29% Part Time, and 4% Contract. Highlights an 89% Physical, 1% Hybrid, and 10% Remote job distribution, with an average salary of $84,039 per year, or $40.4 per hour.

Commercial Roofing Services - Independent Contractor Companies

City Wide Facility Solutions

Carol Stream, IL

Contractor

Posted 18 days ago

Job description

Description

City Wide Facility Solutions is the largest management company in the building maintenance industry. We secure and manage commercial contracts and partner with skilled independent contractors to perform the work. We handle the sales, client communication, billing, and collections - so you can focus on doing what you do best.

We are selectively partnering with established Independent Contractors and service companies to service our commercial clients in the region. If you operate a structured business, deliver professional facility maintenance, restoration, or renovation services, and are looking for steady, recurring work - without the burden of chasing new contracts or managing collections - this may be a strong fit.

City Wide helps you grow your revenue, keep your crews busy, and get paid consistently - including guaranteed payment on the 10th for work performed.

We operate throughout South Chicagoland and Northwest Indiana - a strong commercial market with warehouses, medical facilities, manufacturing sites, schools, and municipal buildings.

For more information, contact Sandra Rivas at 708-365-8535 or chicagoshores-ic@gocitywide.com.

Requirements

We are selectively partnering with contractors who meet the following:

  • Proven experience in commercial roofing (required)
  • Proper licensing for commercial roofing work (as applicable)
  • General liability insurance and workers' compensation coverage
  • Ability to assess, quote, and execute projects independently
  • Professional-grade equipment and crew
  • Strong communication and reliability
  • Commitment to safety, quality, and timelines

Preferred:

  • Experience working in occupied commercial or medical environments
  • Ability to provide clear documentation (photos, reports, scope clarity)

The Opportunity

ity Wide Facility Solutions is seeking a qualified commercial roofing contractor to support a current client project within our portfolio.

This is a project-based opportunity with the potential for ongoing work across multiple commercial properties, depending on performance, professionalism, and execution quality.

We manage a large base of commercial clients across office, medical, industrial, and institutional facilities. Our model is built around bringing vetted service providers into well-scoped, professionally managed opportunities—allowing contractors to focus on execution, not sales.

If you are looking to supplement your pipeline with well-defined commercial work and long-term partnership potential, this may be a strong fit.

If this is your company, keep reading.

INDEPENDENT CONTRACTORS MUST PROVIDE THE FOLLOWING:

  • Valid Business License (if necessary for the service type)
  • Worker's Compensation Insurance
  • General Liability Insurance
  • Federal EIN #
  • Other verifiable business
  • 18 years of age minimum
  • Favorable background investigation results
  • You can not be a sole proprietor

The selected contractor will be responsible for delivering high-quality commercial roofing services, which may include:

  • Roof inspections and condition assessments
  • Leak detection and repair
  • Preventative maintenance
  • Partial or full roof replacement (as applicable)
  • Flat roof systems (TPO, EPDM, modified bitumen, etc.)
  • Proper documentation, reporting, and photo verification

Work will be performed in active commercial environments, requiring professionalism, coordination, and adherence to safety standards.

City Wide will:

  • Coordinate with the client
  • Define scope and expectations
  • Manage communication and administrative flow

You focus on:

Executing the work at a high level

Benefits

We help you grow a real business - not just pick up extra work.

  • Consistent, Recurring Contracts (No Hunting Required)

We bring you qualified commercial accounts so you can focus on operations - not cold calling, bidding, or chasing leads.

  • Reliable, On-Time Payments

Eliminate collections headaches. We handle billing and client payment - you get paid consistently and predictably.

  • Scale Your Revenue Quickly

Access multiple accounts across our territory - grow from a small crew to a multi-team operation with steady work.

  • Professional Account Management Support

Our Facility Solutions Managers handle client communication, inspections, and issue resolution - helping you retain accounts and maintain high standards.

  • No Sales, No Admin Burden

We manage contracts, client expectations, and service coordination - freeing you to focus on delivering quality work and building your team.

  • 20+ Other Opportunities

Expand into additional services (floor care, porter services, consumables, specialty cleaning) and increase revenue per account.

  • Long-Term Partnership Model

We are invested in your growth - many of our partners have scaled into six-figure and multi-crew businesses with us.

Apply