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Independent Contractor Insurance Jobs in Itasca, IL

MCSW Capital Enterprises LLC

Contractor

Chicago, IL · On-site

... TForce insurance and documentation requirements * Must be comfortable working independently and ... independent contractor with MCSW Capital Enterprises LLC while providing contracted courier ...

HealthMarkets, Inc.

Insurance Agent

Chicago, IL · 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 ...

HealthMarkets, Inc.

Insurance Agent

Aurora, IL · 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 JobsIndependent Contractor Insurance JobsIndependent Contractor Insurance Jobs in Itasca, IL

Independent Contractor Insurance information

See Itasca, IL salary details

$383

$1.1K

$2K

How much do independent contractor insurance jobs pay per week?

As of Sep 4, 2026, the average weekly pay for independent contractor insurance in Itasca, IL is $1,060.63, according to ZipRecruiter salary data. Most workers in this role earn between $701.92 and $1,178.85 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 Itasca, IL?

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

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

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

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

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

Independent Contractor Insurance jobs near you
Infographic showing various Independent Contractor Insurance job openings in Itasca, IL as of June 2026, with employment types broken down into 1% As Needed, 61% Full Time, 7% Part Time, 29% Contract, and 2% Nights. Highlights an 90% Physical, 1% Hybrid, and 9% Remote job distribution, with an average salary of $55,153 per year, or $26.5 per hour.

Contractor

MCSW Capital Enterprises LLC

Chicago, IL • On-site

Other

Posted 4 days ago

Job description

Position: Independent Contractor Courier Driver – TForce Route


MCSW Capital Enterprises LLC is seeking a reliable, professional Independent Contractor Courier Driver to operate a dedicated TForce Logistics route.


Position Details


* Contract/Independent Contractor position

* On-site route-based work

* Car, SUV, or minivan required

* Scheduled courier deliveries and pickups

* Must be dependable, punctual, and able to follow assigned route instructions

* Must provide professional customer service and communicate effectively

* Must maintain accurate delivery records and handle customer freight responsibly


Driver Requirements


* Valid driver’s license

* Reliable vehicle that meets TForce requirements

* Current vehicle registration and insurance

* Successful background check and Motor Vehicle Report

* Ability to complete required TForce/SCI onboarding

* Ability to meet all applicable TForce insurance and documentation requirements

* Must be comfortable working independently and completing an assigned route on schedule


This is an opportunity to work as an independent contractor with MCSW Capital Enterprises LLC while providing contracted courier services through TForce Logistics.


Interested applicants should apply with their current contact information, driving experience, and vehicle information.

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