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Job Remote Jobs in Chicago, IL (NOW HIRING)

HMG Careers

Remote Sales Representative

Stickney, IL · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Remote Benefits Advisor

Oak Lawn, IL · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Sales Coordinator Remote

Gary, IN · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Sales Coordinator Remote

Gilberts, IL · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Remote Sales Representative

East Chicago, IN · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Sales Coordinator Remote

Grant Park, IL · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Remote Sales Representative

Markham, IL · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Sales Coordinator Remote

Palos Heights, IL · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Sales Representative Remote

Brookfield, IL · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Remote Sales Representative

Ridgefield, IL · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Remote Sales Representative

Melrose Park, IL · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Sales Coordinator Remote

Gary, IN · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Remote Sales Representative

Libertyville, IL · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Sales Manager Remote

Maywood, IL · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Sales Manager Remote

Hometown, IL · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Remote Sales Representative

Chesterton, IN · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

HMG Careers

Sales Coordinator Remote

Crest Hill, IL · Remote

$69K/yr

Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work ...

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Showing results 21-40

All JobsJob JobsJob Remote JobsJob Remote Jobs in Chicago, IL

Job Remote information

What is the difference between Job Remote vs Job On-site?

AspectJob RemoteJob On-site
Work EnvironmentWork from anywhere, often from home or a chosen locationWork at a designated company location or office
Required CredentialsSimilar to on-site roles; often requires relevant skills and experienceSame as remote roles; credentials depend on the position
Employer UsageCommon in tech, customer service, writing, and digital fieldsPrevalent across industries like manufacturing, retail, and healthcare
Search & Comparison IntentPeople looking for flexible work options or location independenceIndividuals seeking traditional, in-office roles

Job Remote and Job On-site differ primarily in work environment and location flexibility. Remote roles allow employees to work from anywhere, while on-site jobs require presence at a specific location. Both roles often require similar skills and credentials, but the choice depends on personal preference and industry needs.

What are the most commonly searched types of Job jobs in Chicago, IL? The most popular types of Job jobs in Chicago, IL are:
Infographic showing various Job Remote job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 72% Full Time, 21% Part Time, and 6% Contract. Highlights an 95% Physical, 1% Hybrid, and 4% Remote job distribution.

Remote Sales & Engagement Associate

Stratford Davis

Chicago, IL • Remote

$85K - $150K/yr

Full-time

Medical, Dental, Vision, Life, PTO

Posted 2 days ago

New

Job description

Drive Success Through Digital Connections.

We are seeking an enthusiastic Remote Sales & Engagement Associate to join our fast-growing remote team. In this role, you will engage directly with clients through digital channels, uncover their long-term financial goals, and deliver customized solutions that protect what matters most to them.

Core Responsibilities
  • Prospect Engagement: Initiate conversations with prospective clients through active outreach, social channels, and networking.
  • Needs Analysis: Conduct virtual sessions to discover financial gaps and present tailored product options.
  • Relationship Retention: Maintain trusted, long-term advisor relationships to ensure high client satisfaction.
  • Professional Standards: Execute all business activities with total transparency, professionalism, and industry compliance.
Candidate Qualifications
  • High energy, positive attitude, and a strong drive to succeed in a performance-focused environment.
  • Comfortable holding video consultations and communicating clearly over digital channels.
  • Goal-oriented mindset paired with strong time-management discipline.
  • Prior experience in customer service or sales is a bonus, but comprehensive training will be provided.
Compensation & Benefits
  • Work-Life Alignment: Work fully from home with full control over your daily calendar.
  • Turnkey Training System: Comprehensive onboarding pipeline designed to take you from beginner to top producer.
  • Incentives & Recognition: Quarterly awards, financial bonuses, and company-sponsored vacation packages.
  • Benefits Options: Access to life insurance and healthcare exchange options (medical, dental, vision).
  • Commission-Driven Opportunity: Income for this position is entirely commission-based. By removing standard earning ceilings, your revenue potential directly aligns with your dedication, output, and client results.
Apply Today: Submit your resume to take the next step toward launching your remote sales career.