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Insurance Executive Assistant Remote Jobs in Chicago, IL

Lone Star Careers

Sales Executive - Remote

Aurora, IL · Remote

$69K - $150K/yr

  • Medical

  • Dental

Remote Insurance Representative | Flexible Schedule | Commission Only This position offers flexible ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

Lone Star Careers

Sales Executive - Remote

Chicago, IL · Remote

$69K - $150K/yr

  • Medical

  • Dental

Remote Insurance Representative | Flexible Schedule | Commission Only This position offers flexible ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

Lone Star Careers

Remote Sales Executive

Gary, IN · Remote

$69K - $150K/yr

  • Medical

  • Dental

Remote Insurance Representative | Flexible Schedule | Commission Only This position offers flexible ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

Lone Star Careers

Sales Executive - Remote

Joliet, IL · Remote

$69K - $150K/yr

  • Medical

  • Dental

Remote Insurance Representative | Flexible Schedule | Commission Only This position offers flexible ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

Lone Star Careers

Remote Sales Executive

Aurora, IL · Remote

$69K - $150K/yr

  • Medical

  • Dental

Remote Insurance Representative | Flexible Schedule | Commission Only This position offers flexible ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

Lone Star Careers

Remote Sales Executive

Elk Grove Village, IL · Remote

$69K - $150K/yr

  • Medical

  • Dental

Remote Insurance Representative | Flexible Schedule | Commission Only This position offers flexible ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

Lone Star Careers

Remote Sales Executive

Joliet, IL · Remote

$69K - $150K/yr

  • Medical

  • Dental

Remote Insurance Representative | Flexible Schedule | Commission Only This position offers flexible ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

Lone Star Careers

Remote Sales Executive

Elgin, IL · Remote

$69K - $150K/yr

  • Medical

  • Dental

Remote Insurance Representative | Flexible Schedule | Commission Only This position offers flexible ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

Lone Star Careers

Remote Account Executive

Aurora, IL · Remote

$69K - $150K/yr

  • Medical

  • Dental

Remote Insurance Representative | Flexible Schedule | Commission Only This position offers flexible ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

Lone Star Careers

Remote Account Executive

Naperville, IL · Remote

$69K - $150K/yr

  • Medical

  • Dental

Remote Insurance Representative | Flexible Schedule | Commission Only This position offers flexible ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

Lone Star Careers

Remote Account Executive

Gary, IN · Remote

$69K - $150K/yr

  • Medical

  • Dental

Remote Insurance Representative | Flexible Schedule | Commission Only This position offers flexible ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

Lone Star Careers

Remote Account Executive

Joliet, IL · Remote

$69K - $150K/yr

  • Medical

  • Dental

Remote Insurance Representative | Flexible Schedule | Commission Only This position offers flexible ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

Lone Star Careers

Remote Account Executive

Chicago, IL · Remote

$69K - $150K/yr

  • Medical

  • Dental

Remote Insurance Representative | Flexible Schedule | Commission Only This position offers flexible ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

Lone Star Careers

Remote Account Executive

Elgin, IL · Remote

$69K - $150K/yr

  • Medical

  • Dental

Remote Insurance Representative | Flexible Schedule | Commission Only This position offers flexible ... Present benefit programs and assist clients with enrollment * Build and maintain strong client ...

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Showing results 21-40

All JobsInsurance JobsInsurance Executive Assistant Remote JobsInsurance Executive Assistant Remote Jobs in Chicago, IL

Insurance Executive Assistant Remote information

See Chicago, IL salary details

$30.9K

$66.4K

$105.6K

How much do insurance executive assistant remote jobs pay per year?

As of Aug 14, 2026, the average yearly pay for insurance executive assistant remote in Chicago, IL is $66,399.00, according to ZipRecruiter salary data. Most workers in this role earn between $51,500.00 and $77,300.00 per year, depending on experience, location, and employer.

How does an insurance executive assistant effectively manage communication and workflow in a remote setting?

As a remote Insurance Executive Assistant, you'll rely heavily on digital tools to coordinate schedules, handle confidential documents, and facilitate communication between executives, clients, and internal teams. Maintaining clear, organized channels—such as shared calendars, secure email, and project management platforms—is essential to keeping tasks on track and ensuring timely responses. Regular virtual check-ins and proactive updates help keep everyone aligned, and being adaptable to shifting priorities is key in the fast-paced insurance environment. Building trust through responsiveness and attention to detail is especially important when working remotely.

What are the key skills and qualifications needed to thrive as an insurance executive assistant remote?

To thrive as an Insurance Executive Assistant (Remote), you need strong organizational abilities, attention to detail, and a background in administrative support, preferably with knowledge of the insurance industry. Familiarity with office software (like Microsoft Office), CRM platforms, and document management systems is typically required, and certifications such as Certified Administrative Professional (CAP) may be beneficial. Excellent communication, discretion, and time-management are crucial soft skills for managing sensitive information and supporting executives remotely. These skills and qualities are essential to ensure efficient operations, maintain compliance, and provide reliable support in a fast-paced virtual environment.

What does an insurance executive assistant do when working remotely?

An Insurance Executive Assistant working remotely provides high-level administrative support to insurance executives, such as managing schedules, coordinating meetings, handling correspondence, and preparing reports. They also often assist with client communications, maintain confidential records, and help with project management tasks. Working remotely, they leverage technology to stay connected and ensure that executives remain organized and efficient. Attention to detail, strong communication skills, and proficiency with office software are essential for this role.

What are popular job titles related to Insurance Executive Assistant Remote jobs in Chicago, IL?

For Insurance Executive Assistant Remote jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Insurance Executive Assistant Remote jobs in Chicago, IL look for?

The top searched job categories for Insurance Executive Assistant Remote jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Insurance Executive Assistant Remote jobs?

Cities near Chicago, IL with the most Insurance Executive Assistant Remote job openings:

Insurance Executive Assistant Remote jobs near you
Infographic showing various Insurance Executive Assistant Remote job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 74% Full Time, 20% Part Time, and 5% Contract. Highlights an 95% Physical, 2% Hybrid, and 3% Remote job distribution, with an average salary of $66,399 per year, or $31.9 per hour.

Sales Executive - Remote

Lone Star Careers

Aurora, IL • Remote

$69K - $150K/yr

Contractor

Medical, Dental

Re-posted 18 hours ago

Job description

Remote Insurance Representative | Flexible Schedule | Commission Only

This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely, serving clients by providing guidance and protection solutions for individuals and families.

What We Offer
  • Remote, work-from-home career
  • Average first-year earnings of $69K through commissions and bonuses
  • Increased earning potential in later years through performance and renewals
  • Residual income opportunities through client renewals
  • Unionized position with stock options
  • Comprehensive benefits package including medical, dental, and prescription coverage
  • Ongoing training and mentorship from experienced managers
  • High-quality leads provided with no cold calling friends or family
  • Flexible scheduling within a career-focused structure
  • Advancement and recognition opportunities with promotion from within
  • Supportive and collaborative virtual team environment
Qualities We Value
  • Willingness to learn and be coached through structured training
  • Friendly, outgoing, and professional communication style
  • Genuine desire to help others by providing guidance and solutions
  • Strong verbal communication and relationship-building skills
  • Sales or customer service experience is helpful but not required
Qualifications
  • Laptop or desktop computer with a working camera
  • Insurance license required or willingness to obtain one
  • Basic computer skills
  • Must reside in North America including the United States or Canada
  • We do not hire candidates residing outside North America
Responsibilities
  • Contact provided leads to schedule virtual meetings with clients
  • Present benefit programs and assist clients with enrollment
  • Build and maintain strong client relationships
  • Work closely with your manager to set goals and achieve them