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Contractor Insurance Jobs in Cleveland, OH (NOW HIRING)

Dropoff

Driver Contractor

Cleveland, OH · On-site

$16.25 - $20.25/hr

Registered, insured, and inspected car, SUV, or van that is less than 10 years old * Valid driver ... Contractor Delivery Driver with Dropoff, complete the application form to get started. All ...

Dropoff, Inc.

Driver Contractor

Cleveland, OH · On-site

$16.25 - $20.25/hr

Registered, insured, and inspected car, SUV, or van that is less than 10 years old * Valid driver ... Contractor Delivery Driver with Dropoff, complete the application form to get started. All ...

Dropoff, Inc

Driver Contractor

Cleveland, OH · On-site

$16.25 - $20.25/hr

Registered, insured, and inspected car, SUV, or van that is less than 10 years old * Valid driver ... Contractor Delivery Driver with Dropoff, complete the application form to get started. All ...

Pioneer Agency

Insurance Agent

Akron, OH · Remote

$50K - $75K/yr

We are a fast-growing insurance agency helping individuals and families with life, health, and ... Commission-based (independent contractor) with bonus opportunities Schedule: * Flexible hours * Set ...

Promoted2

Remote Insurance Agent

Akron, OH · Remote

$60K - $110K/yr

Remote Insurance Sales Agent | $60k-$110k+ First Year | No Cold Calling Earn strong first-year ... Background in remote or independent contracting roles * Leadership or team-building experience ...

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Showing results 21-40

All JobsContractor Insurance JobsContractor Insurance Jobs in Cleveland, OH

Contractor Insurance information

See Cleveland, OH salary details

$36.4K

$80.3K

$118.8K

How much do contractor insurance jobs pay per year?

As of Aug 14, 2026, the average yearly pay for contractor insurance in Cleveland, OH is $80,300.00, according to ZipRecruiter salary data. Most workers in this role earn between $64,500.00 and $96,000.00 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?

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 Cleveland, OH?

For Contractor Insurance jobs in Cleveland, OH, the most frequently searched job titles are:

What job categories do people searching Contractor Insurance jobs in Cleveland, OH look for?

The top searched job categories for Contractor Insurance jobs in Cleveland, OH are:

What cities near Cleveland, OH are hiring for Contractor Insurance jobs?

Cities near Cleveland, OH with the most Contractor Insurance job openings:

Contractor Insurance jobs near you
Infographic showing various Contractor Insurance job openings in Cleveland, OH as of August 2026, with employment types broken down into 1% As Needed, 74% Full Time, 20% Part Time, and 5% Contract. Highlights an 91% Physical, 1% Hybrid, and 8% Remote job distribution, with an average salary of $80,300 per year, or $38.6 per hour.

Insurance Agent - OH Talent Pipeline

American Family Insurance

Akron, OH • On-site

Other

Re-posted 6 days ago

American Family Insurance rating

7.5

Company rating: 7.5 out of 10

Based on 135 frontline employees who took The Breakroom Quiz

221st of 307 rated insurance

Job description

We’re always looking for strong leaders and motivated individuals to become Agency Agent! While this isn’t a posting for an immediate opening, it’s your gateway to be considered in our talent pipeline for upcoming / future opportunities across Ohio. If you don’t see an active posting in your preferred location, submit your application here to take the first step toward making your dream a reality.

At American Family, we're seeking highly motivated individuals with a demonstrated track record of success and eagerness to accomplish something that takes time, energy, and commitment. Do you possess a strong work ethic and have an inner drive that makes you hungry for success? 

Insurance Agents operate as independent contractors, representing American Family and its products exclusively.  As an insurance agent, you'll be responsible for your agency's overall management, sales, and growth.  You'll also hire your team and work with them to meet the strategic business goals you set.

Reasons why you should become an American Family Insurance Agent:

  • Financially Fit: American Family has the financial security to protect the dreams of your policy holders
  • Fortune 500 company that is among the largest Property and Casualty insurance groups
  • Offer American Family Insurance products as well as products and services through our subsidiary partners
  • Training and support from a local team – from marketing, prospecting, business consultation and more
  • Unlimited compensation potential including a New Agent Incentive Program

Requirements

  • Obtain Property and Casualty and Life insurance licenses
  • Ability to pass a motor vehicle, financial/credit and criminal background check

We believe people are an organization’s most valuable asset, and their ideas and experiences matter. From our CEO to our agency force, we’re committed to growing a diverse and inclusive culture that empowers innovation that will inspire, protect, and restore our customers’ dreams in ways never imagined.

#LI-AH1

What American Family Insurance employees say

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