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Remote Sales Representative Jobs in Chicago, IL (NOW HIRING)

Symmetry

Remote Sales Representative

Chicago, IL · On-site +1

$75K - $180K/yr

Remote Sales Representative Must be authorized to work in the US, no work visas offered at this time Organization Description: At The William Agency, we provide a range of life insurance solutions ...

Symmetry

Remote Sales Representative

Chicago, IL · Remote

$75K - $180K/yr

Remote Sales Representative Must be authorized to work in the US, no work visas offered at this time Organization Description: At The William Agency, we provide a range of life insurance solutions ...

Camesi Agency

Sales Manager Remote

Chicago, IL · Remote

$80K - $120K/yr

Recruit, onboard, and train new sales representatives; maintain ongoing development through role ... What we offer: * 100% remote work with a flexible schedule. * Competitive compensation structure ...

Globe Life Insurance

Be Seen First

Entry Level Insurance Sales Representative (100% Remote)

Naperville, IL · Remote

$60K - $80K/yr

Entry Level Insurance Sales Representative (100% Remote) 100% Remote | United States & Canada | Full-Time | Weekly Pay | Training Provided | No Cold Calling A Remote Sales Career With a Real Starting ...

Globe Life Insurance

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Entry Level Insurance Sales Representative (100% Remote)

Chicago, IL · Remote

$60K - $80K/yr

Entry Level Insurance Sales Representative (100% Remote) 100% Remote | United States & Canada | Full-Time | Weekly Pay | Training Provided | No Cold Calling A Remote Sales Career With a Real Starting ...

Globe Life Insurance

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Entry Level Insurance Sales Representative (100% Remote)

Chicago, IL · Remote

$60K - $80K/yr

Entry Level Insurance Sales Representative (100% Remote) 100% Remote | United States & Canada | Full-Time | Weekly Pay | Training Provided | No Cold Calling A Remote Sales Career With a Real Starting ...

Globe Life Insurance

Be Seen First

Entry Level Insurance Sales Representative (100% Remote)

Naperville, IL · Remote

$60K - $80K/yr

Entry Level Insurance Sales Representative (100% Remote) 100% Remote | United States & Canada | Full-Time | Weekly Pay | Training Provided | No Cold Calling A Remote Sales Career With a Real Starting ...

Globe Life Insurance

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Entry Level Insurance Sales Representative (100% Remote)

Chicago, IL · Remote

$60K - $80K/yr

Entry Level Insurance Sales Representative (100% Remote) 100% Remote | United States & Canada | Full-Time | Weekly Pay | Training Provided | No Cold Calling A Remote Sales Career With a Real Starting ...

Globe Life Insurance

Be Seen First

Entry Level Insurance Sales Representative (100% Remote)

Naperville, IL · Remote

$60K - $80K/yr

Entry Level Insurance Sales Representative (100% Remote) 100% Remote | United States & Canada | Full-Time | Weekly Pay | Training Provided | No Cold Calling A Remote Sales Career With a Real Starting ...

AO Globe Life

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Remote Entry Level Sales Representative - No Experience Needed

Joliet, IL · Remote

$60K - $80K/yr

Remote Entry Level Sales Representative - No Experience Needed Remote | Full-Time | U.S. & Canada | Training Provided | Flexible Schedule Build a Sales Career Without Starting From Scratch A strong ...

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Remote Sales Representative information

See Chicago, IL salary details

$23.7K

$79K

$145.8K

How much do remote sales representative jobs pay per year?

As of Aug 29, 2026, the average yearly pay for remote sales representative in Chicago, IL is $78,992.00, according to ZipRecruiter salary data. Most workers in this role earn between $55,100.00 and $95,800.00 per year, depending on experience, location, and employer.

What is a remote sales representative?

A Remote Sales Representative is a sales professional who works from a location outside of a traditional office, often from home or another remote setting. They are responsible for reaching out to potential customers, presenting products or services, and closing sales, primarily through phone calls, emails, and virtual meetings. This role requires strong communication skills, self-motivation, and the ability to work independently while meeting sales targets. Remote sales representatives often use digital tools and CRM software to manage leads and track sales activities. The flexibility of this job allows companies to tap into a wider talent pool and enables employees to work from virtually anywhere.

What does a remote sales representative do?

Remote sales representatives communicate with customers on a regular basis to sell one product or multiple services via phone calls. These professionals do the same job as regular sales reps but with the option of making commission and performing responsibilities from home. As a remote sales rep, you take the initiative to locate and contact the customer, using persuasive techniques and your excellent interpersonal skills to negotiate and secure sales. You focus on developing each client relationship to foster opportunities for future business. In this role, you also establish sales targets and outcomes, setting deadlines and coordinating sales efforts among team members.

What are the key skills and qualifications needed to thrive as a remote sales representative?

To thrive as a Remote Sales Representative, you need strong sales acumen, product knowledge, and typically a background in business or communications. Familiarity with CRM software like Salesforce, video conferencing tools, and digital communication platforms is essential. Outstanding self-motivation, resilience, and effective virtual communication skills distinguish top performers in this remote environment. These abilities are vital for building client relationships, meeting sales targets, and maintaining productivity outside a traditional office setting.

What are some common challenges faced by remote sales representatives, and how can they be effectively managed?

Remote Sales Representatives often encounter challenges such as building rapport with clients without face-to-face interaction, staying motivated while working independently, and managing time across different time zones. To overcome these obstacles, it's important to leverage video calls and personalized communication tools, establish a structured daily routine, and use CRM software to keep track of leads and follow-ups. Regular virtual team meetings and ongoing training can also foster a sense of connection and ensure alignment with team goals.

Can a remote sales representative work remotely?

Yes, a remote sales representative typically works remotely, using digital communication tools like email, phone, and video conferencing to connect with clients and manage sales activities. The role often requires self-motivation, strong communication skills, and familiarity with customer relationship management (CRM) software. Many companies offer flexible schedules for remote sales positions, but specific requirements may vary by employer.
More about Remote Sales Representative jobs

What are the most commonly searched types of Sales Representative jobs in Chicago, IL?

The most popular types of Sales Representative jobs in Chicago, IL are:

What are popular job titles related to Remote Sales Representative jobs in Chicago, IL?

For Remote Sales Representative jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Remote Sales Representative jobs in Chicago, IL look for?

The top searched job categories for Remote Sales Representative jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Remote Sales Representative jobs?

Cities near Chicago, IL with the most Remote Sales Representative job openings:

Remote Sales Representative jobs near you
Infographic showing various Remote Sales Representative job openings in Chicago, IL as of August 2026, with employment types broken down into 77% Full Time, 21% Part Time, 1% Contract, and 1% Nights. Highlights an 76% Physical, 1% Hybrid, and 23% Remote job distribution, with an average salary of $78,992 per year, or $38 per hour.

Work Remote | Part-Time Sales | Uncapped Potential

Winnetka, IL • On-site, Remote

Choate Agency
See more jobs at Choate Agencyexternal

$75K - $80K/yr

Part-time

Re-posted 21 days ago

Job description

Account Sales Representative
Work from Phone | Flexible Hours | Commission-Based | Warm Leads Available
Looking for a flexible, remote side income that actually pays what you're worth? Choate Agency, part of Symmetry Financial Group, is hiring part-time sales reps who want to work from their phone or laptop, on their own time-with no cold calls, no pressure, and no ceiling on earnings.
🔑 What You'll Love:
  • 📱 Work from your phone and tablet - 100% remote sales
  • ⏰ Set your own hours - Work part-time, nights, or weekends
  • 📞 Only warm leads - No cold calling or spamming friends
  • 💸 High commissions - Earn $500-$1,500+ per sale
  • 📈 Top training & support - We give you the blueprint
💼 What You'll Do:
  • Help families choose life insurance or financial protection
  • Follow our proven script and sales system
  • Submit applications online in minutes
  • (Optional) Grow your own small team for passive income
• Ideal For:
  • Sales reps, side hustlers, or parents needing flexibility
  • Coaches, teachers, or professionals looking to earn more
  • Gig workers (Uber, DoorDash, etc.) ready to level up
💰 Compensation:
  • 100% commission - part-time agents earn $2K-$6K+ monthly
  • Weekly pay | Incentives & bonuses | No cap on income | Results Vary

Get started quickly. No experience? We train the right mindset. Great Benefits.
The Choate Agency offers remote sales positions with top compensation, world-class incentives, and great benefits. Minimal time required weekly is about 8-10 hours.
🔗Apply today.

Apply