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Remote Independent Contractor Jobs in Winnetka, IL

Promoted2

Remote Insurance Agent

Chicago, IL · Remote

$60K - $110K/yr

Background in remote or independent contracting roles * Leadership or team-building experience ... Compensation and Benefits First year: $60,000-$110,000+ Long-term potential: $90,000-$250,000+ 1099 ...

Promoted2

Remote Insurance Agent

Chicago, IL · Remote

$60K - $110K/yr

Background in remote or independent contracting roles * Leadership or team-building experience ... Compensation and Benefits First year: $60,000-$110,000+ Long-term potential: $90,000-$250,000+ 1099 ...

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Remote Independent Contractor information

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$413

$1.1K

$2.2K

How much do remote independent contractor jobs pay per week?

As of Aug 21, 2026, the average weekly pay for remote independent contractor in Winnetka, IL is $1,141.63, according to ZipRecruiter salary data. Most workers in this role earn between $755.77 and $1,269.23 per week, depending on experience, location, and employer.

What is a remote independent contractor?

Remote Independent Contractors are self-employed individuals who provide services to clients or companies from a location outside of a traditional office, often from their own home or another remote setting. They typically manage their own schedules, pay their own taxes, and are responsible for their own equipment and workspace. Unlike employees, independent contractors are not entitled to benefits such as health insurance, paid leave, or retirement plans from the companies they work for. This arrangement offers flexibility but also requires a high degree of self-motivation, organization, and the ability to manage multiple clients or projects.

What does a remote independent contractor do?

A remote independent contractor performs tasks for a client or business on a freelance, often short-term basis. Independent contractor jobs exist in industries such as administration and support, scientific and technical service, health care, publishing, real estate, arts and entertainment, and transportation. As an independent contractor, you sign a contract with a client or business and work to provide a specific service or product at an agreed upon rate. You may need to establish a business license as a remote independent contractor. Because you are not an employee of a business or organization, you can work a flexible schedule from home or otherwise remotely.

What are the key skills and qualifications needed to thrive as a remote independent contractor?

To thrive as a Remote Independent Contractor, you need strong self-management, time management, and subject matter expertise, typically supported by relevant experience or specialized education. Familiarity with collaboration tools like Slack, Zoom, Trello, and cloud-based document sharing, as well as secure file transfer systems, is essential. Outstanding communication, adaptability, and problem-solving skills help you build client trust and efficiently navigate remote work challenges. These capabilities ensure you meet deadlines, maintain productivity, and deliver high-quality results in a flexible, independent work environment.

How do remote independent contractors typically manage communication and collaboration with clients and teams across different time zones?

Remote Independent Contractors often work with clients or collaborators from various regions, making clear and consistent communication crucial. They usually rely on digital tools like email, project management platforms, and video conferencing to stay connected. Setting expectations for response times, scheduling regular check-ins, and being proactive about updates help ensure smooth collaboration despite time zone differences. Flexibility and strong self-management skills are key to maintaining productivity and building trust with clients.

What is the difference between Remote Independent Contractor vs Remote Freelance Writer?

AspectRemote Independent ContractorRemote Freelance Writer
CredentialsVaries by industry, often no formal certification requiredTypically requires writing samples, portfolio, or relevant experience
Work EnvironmentWorks independently, often on multiple projectsWorks remotely, usually on writing assignments for clients
Employer UsageHired directly or through agencies, contracts with businessesHired by clients or agencies for specific writing tasks

Remote Independent Contractors and Remote Freelance Writers both work remotely and independently, but contractors often handle a broader range of tasks and may work across industries, while freelance writers focus specifically on writing projects. The key difference lies in the scope of work and typical credentials, with freelancers usually needing a portfolio to demonstrate their writing skills.

More about Remote Independent Contractor jobs

What are the most commonly searched types of Remote jobs in Winnetka, IL?

The most popular types of Remote jobs in Winnetka, IL are:

What cities near Winnetka, IL are hiring for Remote Independent Contractor jobs?

Cities near Winnetka, IL with the most Remote Independent Contractor job openings:

Remote Independent Contractor jobs near you
Infographic showing various Remote Independent Contractor job openings in Winnetka, IL as of August 2026, with employment types broken down into 52% Full Time, and 48% Contract. Highlights an 100% Remote job distribution, with an average salary of $59,365 per year, or $28.5 per hour.

INDEPENDENT CONTRACTOR - Collision Center Auditor

DEKRA North America

Chicago, IL • On-site, Remote

Part-time

Re-posted 28 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.

Equal Opportunity Employer
This employer is required to notify all applicants of their rights pursuant to federal employment laws. For further information, please review the Know Your Rights notice from the Department of Labor.

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