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Independent Contractor Insurance Jobs in Chicago, IL

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Independent Contractor Insurance information

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$406

$1.1K

$2.1K

How much do independent contractor insurance jobs pay per week?

As of Sep 3, 2026, the average weekly pay for independent contractor insurance in Chicago, IL is $1,122.17, according to ZipRecruiter salary data. Most workers in this role earn between $742.31 and $1,248.08 per week, depending on experience, location, and employer.

What is an independent contractor insurance?

An Independent Contractor Insurance job involves helping self-employed individuals or freelancers secure the right insurance coverage to protect their businesses. This can include general liability, professional liability, workers' compensation, and other policies tailored to their specific industry. Insurance professionals in this role assess risks, recommend policies, and guide clients through the coverage selection process. They may work independently or for an insurance agency, ensuring contractors have the financial protection needed to operate safely and legally.

What skills and qualifications are needed for independent contractor insurance?

To excel as an Independent Contractor Insurance professional, you need a thorough understanding of insurance products, industry regulations, and self-employment management, often backed by appropriate state licensure or credentials. Familiarity with CRM platforms, e-signature tools, and quoting software is vital for managing client accounts and processing insurance applications efficiently. Strong communication, organizational skills, and an entrepreneurial mindset set top performers apart in this field. These abilities help build trust with clients, secure new business, and sustain a successful independent practice.

What are common challenges faced by independent contractor insurance professionals?

Independent Contractor Insurance professionals often face challenges such as sourcing their own clients, managing unpredictable income streams, and staying updated on constantly changing insurance regulations. They typically balance multiple client accounts and must be proactive in networking and marketing their services to build a steady book of business. Working independently also requires self-motivation and discipline, as success is largely determined by the effort you put into client outreach and relationship management. However, the role offers flexibility and the potential for significant earnings growth as you establish a strong client base.

What are the most commonly searched types of Insurance jobs in Chicago, IL?

The most popular types of Insurance jobs in Chicago, IL are:

What are popular job titles related to Independent Contractor Insurance jobs in Chicago, IL?

For Independent Contractor Insurance jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Independent Contractor Insurance jobs in Chicago, IL look for?

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

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

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

Independent Contractor Insurance jobs near you
Infographic showing various Independent Contractor Insurance job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 73% Full Time, 21% Part Time, and 5% Contract. Highlights an 91% Physical, 2% Hybrid, and 7% Remote job distribution, with an average salary of $58,353 per year, or $28.1 per hour.

INDEPENDENT CONTRACTOR - Collision Center Auditor

DEKRA

Chicago, IL • On-site

Part-time

Re-posted 18 days ago

Job description

Do you love working with high end, luxury automotive brands?  Do you have a passion for helping collision centers achieve their goals of ‘highest quality’ and elite Certification status?  Are you interested in INDEPENDENT CONTRACTOR opportunities that will add revenue and variety to your current line of business?  Are you looking to partner with a company who will invest in your training and treat you as a true business partner?

It’s an exciting time at DEKRA North America!  Building off the strength of 47,000+ associates worldwide and leveraging the success of partnerships across the globe, DEKRA is looking for the right individuals to join us as independent contractors and help us exceed collision center expectations.  If others see you as professional; engaging; optimistic; humbly persistent and a student of your business, then please read on.

Here are some highlights of how you will be helping collision centers / OEMs as an independent contractor partnering with DEKRA:

  • Perform audits to ensure compliance with Training, Facility, Repair Procedures, and Tool / Equipment requirements.
  • Document findings, prepare an improvement plan of action and partner with centers on mutually agreed upon next steps for achieving certification.
  • IF you have a training background – Deliver standup training to collision center and dealer personnel on a variety of collision and safety-related curriculum.

DEKRA is one of the world’s leading testing, inspection, and certification (TIC) companies offering innovative professional services in the fields of vehicle inspection, automotive expertise, expert appraisals, industrial product testing & certification, management system certifications, leadership consulting, and much more. As an independent contractor you will partner with an organization with more than 180 subsidiaries in 60+ countries worldwide. DEKRA is a purpose-driven organization with a deep passion to make the world a safer place on the road, at work and home.

Our strong international presence, industry expertise and close ties with the automotive industry have earned us high recognition amongst OEMs, collision centers, dealers, suppliers, and industry service providers. With our broad international network of automotive experts, consultants, and specialists, DEKRA has a proven track record in the improvement of quality, business performance, people skills, workflows, and processes for our customers. We are committed to building long-term, sustainable partnerships with our customers.

To learn more about us: https://www.dekra.us/en/home-page/

We are currently looking for remote INDEPENDENT CONTRACTORS within close proximity to the following territories:

  • Seattle, WA
  • Portland, OR
  • Los Angeles, CA
  • Phoenix, AZ
  • Las Vegas, NV
  • Denver, CO
  • Chicago, IL
  • Dallas/Houston, TX

The following skills and attributes are preferred for the INDEPENDENT CONTRACTOR Collision Center Auditor:

What Makes a Great Candidate:

  • Experience in the collision center and/or mechanical service center industry; collision center management; independent insurance appraisals; or a working knowledge of automotive collision, parts, and service operations.  Time spent delivering stand-up or onsite training a definite PLUS+.
  • Technical automotive background or education.
  • High level of accuracy in verbal & written communication.
  • Good problem-solving, negotiation, and influencing skills.
  • Experienced in Microsoft Office software applications.
  • High level of empathy with the ability to interact with others at all levels in a collision center or dealership.
  • High level of self-management skills and motivation.
  • Strong communication, presentation, and analytical skills.
  • Relevant professional experience and strong social/interpersonal skills.

Travel Considerations:

  • Minimum ability to travel locally and regionally for audits.
  • Nationally, if conducting onsite training.  However, overall % will be very limited.

 Benefits: 

  • As this is an INDEPENDENT CONTRACTOR position initially, benefits are not included.  However, DEKRA has a long history of transitioning independent contractors to full-time employees based on business growth and alignment with your career interests.

Apply