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Remote Work Insurance Jobs in Chicago, IL (NOW HIRING)

Symmetry

Remote Work Sales Position

Chicago, IL · Remote

$60K - $200K/yr

We are looking for Remote Insurance Sales Representatives who can be trained to become a manager ... Work completely remotely. - Experience is not necessary however previous sales or training ...

Symmetry

Remote Work Sales Position

Chicago, IL · Remote

$60K - $200K/yr

We are looking for Remote Insurance Sales Representatives who can be trained to become a manager ... Work completely remotely. - Experience is not necessary however previous sales or training ...

HMG Careers

Remote Insurance Agent

Elgin, IL · Remote

$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... You will work remotely, serving clients by providing guidance and protection solutions for ...

HMG Careers

Remote Insurance Agent

Naperville, IL · Remote

$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... You will work remotely, serving clients by providing guidance and protection solutions for ...

HMG Careers

Remote Insurance Agent

Joliet, IL · Remote

$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... You will work remotely, serving clients by providing guidance and protection solutions for ...

HMG Careers

Remote Insurance Agent

Gary, IN · Remote

$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... You will work remotely, serving clients by providing guidance and protection solutions for ...

HMG Careers

Remote Insurance Agent

Aurora, IL · Remote

$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... You will work remotely, serving clients by providing guidance and protection solutions for ...

HMG Careers

Remote Insurance Agent

Chicago, IL · Remote

$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... You will work remotely, serving clients by providing guidance and protection solutions for ...

HMG Careers

Remote Life Insurance Agent

Aurora, IL · Remote

$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... You will work remotely, serving clients by providing guidance and protection solutions for ...

HMG Careers

Remote Life Insurance Agent

Elgin, IL · Remote

$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... You will work remotely, serving clients by providing guidance and protection solutions for ...

HMG Careers

Remote Life Insurance Agent

Chicago, IL · Remote

$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... You will work remotely, serving clients by providing guidance and protection solutions for ...

HMG Careers

Remote Life Insurance Agent

Joliet, IL · Remote

$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... You will work remotely, serving clients by providing guidance and protection solutions for ...

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Showing results 1-20

All JobsWork Insurance JobsRemote Work Insurance JobsRemote Work Insurance Jobs in Chicago, IL

Remote Work Insurance information

See Chicago, IL salary details

$13

$32

$57

How much do remote work insurance jobs pay per hour?

As of Jul 13, 2026, the average hourly pay for remote work insurance in Chicago, IL is $32.66, according to ZipRecruiter salary data. Most workers in this role earn between $17.07 and $48.03 per hour, depending on experience, location, and employer.

What is the difference between Remote Work Insurance vs Freelance Writer Insurance?

AspectRemote Work InsuranceFreelance Writer Insurance
Credentials/CertificationsTypically no specific credentials requiredMay require proof of professional liability or specific writing-related coverage
Work EnvironmentRemote, often employed by companiesSelf-employed, independent contractor
Employer/Industry UsageUsed by companies hiring remote employeesUsed by freelance writers working independently
Comparison Search IntentYes, often searched togetherYes, related but distinct

Remote Work Insurance generally covers employees working remotely for a company, providing protection against work-related risks. Freelance Writer Insurance is tailored for independent writers, covering professional liability and equipment. While both protect remote workers, the key difference lies in employment status and coverage specifics.

What are some common challenges faced by professionals working in remote work insurance, and how can they be addressed?

Professionals in remote work insurance often face challenges related to communicating complex policy details across virtual channels and staying updated on rapidly evolving regulations affecting remote workers. Building strong relationships with clients and team members can require extra effort due to the absence of in-person interactions. To address these challenges, it's important to leverage digital collaboration tools, schedule regular check-ins, and participate in ongoing training to stay current with industry changes. Proactively sharing updates and maintaining transparent communication can foster trust and streamline workflows within remote teams.

What is remote work insurance?

Remote work insurance is a type of coverage designed to protect businesses and employees who work from home or outside traditional office settings. It typically addresses unique risks associated with remote work, such as equipment damage, cyber liability, and workers' compensation for injuries sustained while working remotely. This insurance ensures that both employers and employees are financially protected against unexpected incidents related to remote work arrangements.

What are the key skills and qualifications needed to thrive as a Remote Work Insurance Specialist, and why are they important?

To thrive as a Remote Work Insurance Specialist, you need expertise in insurance policies, risk assessment, and regulatory compliance, often supported by relevant certifications such as state insurance licenses. Familiarity with digital insurance platforms, CRM systems, and communication tools like Zoom or Slack is essential for managing remote client interactions and documentation. Exceptional self-motivation, time management, and strong communication skills set top performers apart in this position. These skills ensure accurate policy administration, regulatory adherence, and effective service delivery in a remote work environment.
What are popular job titles related to Remote Work Insurance jobs in Chicago, IL? For Remote Work Insurance jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Remote Work Insurance jobs in Chicago, IL look for? The top searched job categories for Remote Work Insurance jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Remote Work Insurance jobs? Cities near Chicago, IL with the most Remote Work Insurance job openings:
Remote Work Insurance jobs near you
Infographic showing various Remote Work Insurance job openings in Chicago, IL as of July 2026, with employment types broken down into 68% Full Time, 28% Part Time, and 4% Contract. Highlights an 100% Remote job distribution, with an average salary of $67,924 per year, or $32.7 per hour.

Sales Representative- Remote Work

GIA Legacy Planning

Crown Point, IN • On-site, Remote

Full-time

Posted 7 days ago

Job description

Sales Representative- Remote Work
Location: Remote Position/Work from Home
Job Type: Full-Time/Part-Time
Compensation: 100% Commission Based
About Us:
GIA Legacy Planning is a dynamic and client-focused insurance agency. We specialize in providing personalized insurance solutions to protect families and businesses. Our culture is built on integrity, mentorship, and professional growth.
We are looking for motivated and results-driven Insurance Sales Representatives to join our growing team. If you have a passion for helping others, enjoy building relationships, and seek an opportunity with unlimited earning potential, we want to hear from you!
Responsibilities:
  • Identify client needs and recommend tailored insurance solutions
  • Develop and maintain strong client relationships
  • Generate leads through networking, referrals, and company-provided resources
  • Educate clients on available policies and coverage options
  • Follow up with prospects to close sales and maintain customer satisfaction
  • Stay informed about industry trends and product offerings
  • Work independently while collaborating with a supportive team

What We Offer:
  • Competitive commission structure with potential for bonuses
  • Flexible work schedule (work from home)
  • Comprehensive training and mentorship programs
  • Access to top-rated insurance carriers and products
  • Opportunities for career growth and leadership development
  • Supportive team culture with ongoing coaching and professional development

Requirements:
  • Insurance license (or willingness to obtain one - we provide guidance)
  • Strong communication and interpersonal skills
  • Self-motivated with a results-driven mindset
  • Ability to work independently and manage time effectively
  • Basic computer skills for CRM and client management

Department Sales Representative - Work from Home Locations Crown Point, IN 46307 Remote status Fully Remote

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