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Entry Level 1099 Jobs in Chicago, IL (NOW HIRING)

Integrityfex

Entry Level Sales Agent

Chicago, IL · Remote

What You'll Do As an Entry-Level Insurance Sales Representative, you will: * Meet with prospective ... Compensation This is a 1099 independent contractor opportunity . Compensation is commission-based.

Integrityfex

Entry Level Sales Agent

Brookfield, IL · Remote

What You'll Do As an Entry-Level Insurance Sales Representative, you will: * Meet with prospective ... Compensation This is a 1099 independent contractor opportunity . Compensation is commission-based.

Integrityfex

Entry Level Sales Agent

Schaumburg, IL · Remote

What You'll Do As an Entry-Level Insurance Sales Representative, you will: * Meet with prospective ... Compensation This is a 1099 independent contractor opportunity . Earnings vary based on individual ...

Integrityfex

Entry Level Sales Agent

Lincolnshire, IL · Remote

What You'll Do As an Entry-Level Insurance Sales Representative, you will: * Meet with prospective ... Compensation This is a 1099 independent contractor opportunity . Earnings vary based on individual ...

Integrityfex

Entry Level Sales Agent

Portage, IN · Remote

What You'll Do As an Entry-Level Insurance Sales Representative, you will: * Meet with prospective ... Compensation This is a 1099 independent contractor opportunity . Compensation is commission-based.

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Entry Level 1099 information

What is an entry level 1099?

Entry Level 1099 jobs are positions where individuals are hired as independent contractors rather than traditional employees, typically with little to no prior experience required. The term '1099' refers to the IRS form used to report income earned by independent contractors. In these roles, workers are responsible for managing their own taxes, benefits, and work expenses. Entry level 1099 jobs can be found in fields like sales, gig work, consulting, and freelance services, offering flexibility but less job security and fewer benefits than standard employment.

What are the key skills and qualifications needed to thrive as an entry level 1099 contractor?

To succeed as an Entry Level 1099 contractor, you generally need strong self-management skills, basic industry knowledge, and the ability to work independently, often without direct supervision. Familiarity with invoicing software, time-tracking tools, and basic accounting systems is typically expected to manage your freelance business. Exceptional communication, adaptability, and organizational skills help you build client relationships and handle multiple projects efficiently. These skills and qualities are important because they enable you to deliver quality work, maintain client satisfaction, and ensure reliable income as an independent contractor.

What are some common challenges faced by entry level 1099 workers, and how can they be addressed?

Entry Level 1099 workers, also known as independent contractors, often face challenges such as managing inconsistent income, handling self-employment taxes, and securing their own benefits like health insurance. To address these, it's important to budget carefully, set aside money for taxes throughout the year, and research affordable health coverage options. Additionally, building strong relationships with clients and maintaining a professional network can help ensure a steady flow of work and provide support as you develop your career.

What is the difference between Entry Level 1099 vs Entry Level W-2?

AspectEntry Level 1099Entry Level W-2
Tax StatusIndependent contractor, responsible for own taxesEmployee, taxes withheld by employer
Work EnvironmentTypically freelance or contract-basedFull-time or part-time employment
CredentialsUsually minimal; depends on industryOften requires onboarding and HR paperwork
Employer UsageUsed by companies for project-based workUsed for regular employment roles

Entry Level 1099 workers operate as independent contractors, handling their own taxes and often working on a freelance basis. In contrast, Entry Level W-2 employees are hired as regular staff, with taxes withheld by the employer. The choice impacts tax responsibilities, work environment, and employer relationships, making it important to understand these differences when seeking entry-level opportunities.

What are the most commonly searched types of 1099 jobs in Chicago, IL?

The most popular types of 1099 jobs in Chicago, IL are:

What are popular job titles related to Entry Level 1099 jobs in Chicago, IL?

For Entry Level 1099 jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Entry Level 1099 jobs in Chicago, IL look for?

The top searched job categories for Entry Level 1099 jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Entry Level 1099 jobs?

Cities near Chicago, IL with the most Entry Level 1099 job openings:

Entry Level 1099 jobs near you

Independent Medicare Supplement Producer (1099)

Team Nexa Insurance Solutions

Chicago, IL • Remote

$55K - $295K/yr

Contractor

Medical, Life

Re-posted 12 days ago

Job description

Team Nexa Insurance Solutions – Health & Medicare Division
Team Nexa Insurance Solutions is expanding its Health & Medicare Division and is seeking licensed, independent Medicare producers who want to build a sustainable book of business with long-term renewal income..  In-person & Remote
Who This Opportunity Is For?
This opportunity is designed for experienced or currently licensed Life & Health insurance agents who are comfortable operating as independent producers and are looking to grow beyond a single-carrier or captive environment.  In-Person & Remote Sales Opportunities.  
 
What You’ll Do

Sell Medicare Supplements and related health products

Work with multiple well-known carriers (non-captive)

Build and manage your own book of business

Operate independently with training, systems, and support provided
 

Ideal Professional Background

Active Life & Health Insurance Producer License

Experience with Medicare Supplements, Medicare Advantage, or health products

Comfortable operating as an independent (1099) agent

Entrepreneurial mindset with a focus on long-term income and renewals
 

What This Is Not

Not a call-center or hourly customer service role

Not a W-2 employment position

Not an entry-level or unlicensed training role
 

What We Offer

Independent 1099 platform

Access to multiple top-tier carriers

Separate training and support for the Health & Medicare Division

Opportunity to expand income through renewals and cross-selling

This is an independent 1099 opportunity, not an employee (W-2) position.
If you currently hold an active Life & Health insurance license and are seeking an independent Medicare opportunity, we’d welcome the conversation.
*Individual Results Wil Vary*

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