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Entry Level Remote Paid Training Jobs in Chicago, IL

Nexera

Entry Level Remote Sales Role

Chicago, IL · Remote

$1.5K - $5.3K/wk

We provide full training and licensing support. Why recent grads choose this over a traditional job ... Paid every week * Performance bonuses and incentives available * Long-term passive income through ...

Nexera

Entry Level Remote Insurance Sales

Chicago, IL · Remote

$1.5K - $3.2K/wk

Attending weekly virtual training with a dedicated mentor * Working toward team leadership and ... Paid weekly * Bonuses and incentives available * Long-term passive income through team building and ...

Nexera

Entry Level Remote Insurance Sales

Chicago, IL · Remote

$1.5K - $3.2K/wk

Attending weekly virtual training with a dedicated mentor * Working toward team leadership and ... Paid weekly * Bonuses and incentives available * Long-term passive income through team building and ...

AO Globe Life

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Remote - Entry Level Client Sales Representative (Training Provided)

Chicago, IL · Remote

$60K - $80K/yr

Remote - Entry Level Client Sales Representative (Training Provided) 100% Remote | U.S. Applicants ... Commission-based compensation paid weekly * Opportunities to take on additional responsibility as ...

New

Globe Life Insurance

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Entry Level Customer Sales Representative (100% Remote)

Aurora, IL · Remote

$60K - $80K/yr

Entry Level Customer Sales Representative (100% Remote) 100% Remote | United States & Canada | Full-Time | Paid Weekly | Training Provided | No Cold Calling A Remote Career With Room to Grow A strong ...

Globe Life Insurance

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Entry Level Customer Sales Representative (100% Remote)

Joliet, IL · Remote

$60K - $80K/yr

Entry Level Customer Sales Representative (100% Remote) 100% Remote | United States & Canada | Full-Time | Paid Weekly | Training Provided | No Cold Calling A Remote Career With Room to Grow A strong ...

Globe Life Insurance

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Entry Level Customer Sales Representative (100% Remote)

Joliet, IL · Remote

$60K - $80K/yr

Entry Level Customer Sales Representative (100% Remote) 100% Remote | United States & Canada | Full-Time | Paid Weekly | Training Provided | No Cold Calling A Remote Career With Room to Grow A strong ...

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Showing results 1-20

All JobsPaid Training JobsEntry Level Remote Paid Training JobsEntry Level Remote Paid Training Jobs in Chicago, IL

Entry Level Remote Paid Training information

See Chicago, IL salary details

$29.4K

$54.8K

$80.9K

How much do entry level remote paid training jobs pay per year?

As of Aug 27, 2026, the average yearly pay for entry level remote paid training in Chicago, IL is $54,754.00, according to ZipRecruiter salary data. Most workers in this role earn between $47,400.00 and $60,800.00 per year, depending on experience, location, and employer.

What is the difference between Entry Level Remote Paid Training vs Customer Service Representative?

AspectEntry Level Remote Paid TrainingCustomer Service Representative
CredentialsNo prior experience required; training providedHigh school diploma or equivalent; on-the-job training
Work EnvironmentRemote, flexible hours during trainingRemote or in-office, depending on employer
Industry UsageCommon in various industries for onboardingCustomer support across multiple sectors
Search IntentEntry-level remote jobs with paid trainingRemote customer service roles with training

Entry Level Remote Paid Training positions focus on onboarding new employees with no prior experience, offering paid training to prepare them for the role. Customer Service Representatives typically require some basic qualifications but also benefit from employer-provided training. Both roles are often remote, making them accessible for job seekers seeking flexible, entry-level opportunities with paid training.

What are the most commonly searched types of Remote Paid Training jobs in Chicago, IL?

The most popular types of Remote Paid Training jobs in Chicago, IL are:

Entry Level Remote Paid Training jobs near you
Infographic showing various Entry Level Remote Paid Training job openings in Chicago, IL as of August 2026, with employment types broken down into 50% Full Time, and 50% Part Time. Highlights an 50% In-person, and 50% Remote job distribution, with an average salary of $54,754 per year, or $26.3 per hour.

Entry Level Sales Representative - Remote | 80K + | Training Provided | Inhouse leads

Meron & Kemboi Financial Agency

Chicago, IL • Remote

$3.5K - $5.5K/wk

Full-time

Re-posted 7 days ago

Job description

We are currently expanding and looking for motivated individuals to join our team in an entry-level remote sales position.

No prior experience is required. We provide full training, mentorship, and a proven system to help you succeed from day one.

This is a work-from-home opportunity where you will be speaking with clients who have already requested information about life insurance coverage. There is no cold calling involved.

What you’ll be doing:
• Following up with warm, inbound leads
• Running virtual appointments over phone or Zoom
• Helping clients find coverage that fits their needs
• Learning and applying a proven sales system

Who this is a great fit for:
Entry-level candidates, career changers, customer service reps, teachers, realtors, mortgage professionals, and individuals looking to build a high-income skill set.

What we provide:
• Full training and ongoing mentorship
• Flexible schedule (part-time or full-time)
• Warm leads (no cold calling)
• Proven system designed for beginners
• Opportunity to earn $100K+

Compensation:
This is a 100% commission-based position with uncapped earning potential.
Starting commission begins at 80%, with opportunities for advancement based on performance.

If you are coachable, motivated, and ready to learn a new skill that can change your income, apply today.