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Remote Sales Rep ~ Jobs in Chicago, IL (NOW HIRING)

Remote Sales Representative

Chicago, IL ยท 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 ...

Remote Sales Representative

Chicago, IL ยท 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 ...

Sales Manager Remote

Chicago, IL ยท 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 ...

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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 ...

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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 ...

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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 ...

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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 ...

Be Seen First

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 ...

Be Seen First

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 ...

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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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Showing results 1-20

Remote Sales Rep information

See Chicago, IL salary details

$23.7K

$79K

$145.8K

How much do remote sales rep ~ jobs pay per year?

As of Aug 30, 2026, the average yearly pay for remote sales rep ~ 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 rep ~?

A Remote Sales Rep is responsible for selling products or services while working outside of a traditional office setting, usually from home. The job involves reaching out to potential customers, building relationships, and closing sales through phone calls, emails, and virtual meetings. Successful remote sales reps must be self-motivated, have strong communication skills, and be comfortable using digital tools to manage leads and track progress. This role often offers flexibility in work hours and location, making it ideal for independent, goal-driven individuals.

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

To thrive as a Remote Sales Rep, you need strong communication, negotiation, and customer relationship management skills, often supported by a background in sales or business and a proven track record of meeting targets. Familiarity with CRM platforms like Salesforce or HubSpot, as well as proficiency in video conferencing and email outreach tools, is typically required. Exceptional self-motivation, time management, and problem-solving abilities help individuals excel in this remote environment. These skills are crucial for building client trust, closing deals, and consistently achieving sales goals while working independently.

What are some common challenges faced by remote sales reps ~, and how can they be addressed?

One common challenge for Remote Sales Reps is maintaining consistent communication and engagement with prospects and clients without the benefit of in-person meetings. Staying motivated and organized while working independently can also be demanding, as there are fewer immediate touchpoints with managers or team members. To address these challenges, it's important to establish a structured daily routine, leverage collaborative tools for regular check-ins, and actively participate in virtual team meetings. Successful reps also set clear goals for themselves and use CRM systems to track and nurture leads efficiently.

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. Many companies offer flexible or fully remote positions for sales roles, provided the employee has a suitable home office setup and strong communication skills.

How much do remote sales representatives make?

Remote sales representatives typically earn an average annual salary ranging from $40,000 to $70,000, with top performers earning over $100,000 including commissions and bonuses. Compensation often depends on experience, industry, sales skills, and the company's commission structure.

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

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

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

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

Infographic showing various Remote Sales Rep ~ job openings in Chicago, IL as of August 2026, with employment types broken down into 85% Full Time, and 15% Part Time. Highlights an 100% Remote job distribution, with an average salary of $78,992 per year, or $38 per hour.

Work Remote | Part-Time Sales | Uncapped Potential

Choate Agency

Winnetka, IL โ€ข On-site, Remote

$75K - $80K/yr

Part-time

Re-posted 23 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.
๐Ÿ”‘ What You'll Love:
  • ๐Ÿ“ฑ Work from your phone and tablet - 100% remote sales
  • โฐ Set your own hours - Work part-time, nights, or weekends
  • ๐Ÿ“ž Only warm leads - No cold calling or spamming friends
  • ๐Ÿ’ธ High commissions - Earn $500-$1,500+ per sale
  • ๐Ÿ“ˆ Top training & support - We give you the blueprint
๐Ÿ’ผ 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
โ€ข 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
๐Ÿ’ฐ 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.

๐Ÿ”—Apply today.