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1099 Position Jobs in Boston, MA (NOW HIRING)

Pierre Strand

Sales Representative

Boston, MA · On-site

Uncapped commission structure (1099 position) * Flexible working hours * 100% remote * Appointments provided, no cold calling We're looking for the best of the best, So, if you feel like there's no ...

AO Premier

Be Seen First

Benefits Specialist

Boston, MA · Remote

$60K - $80K/yr

Commission only, 1099 position. Watch this company overview video and then schedule your interview once you have completed the video. Must be authorized to work in the USA. Responsibilities

Pierre Strand

Remote Sales Person

Boston, MA · On-site +1

Bid farewell to income restrictions; our uncapped commission structure in this 1099 position allows you to reap the rewards of your hard work. * Embrace the complete flexibility of remote work ...

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1099 Position information

What is a 1099 position?

A 1099 position refers to a job where an individual works as an independent contractor rather than as a traditional employee. Instead of receiving a W-2 form from an employer, workers in 1099 positions receive a 1099-NEC form to report their earnings for tax purposes. These workers are responsible for their own taxes, benefits, and work expenses. 1099 positions offer more flexibility but less job security and fewer benefits compared to regular employment.

What are the key skills and qualifications needed to thrive in a 1099 (independent contractor) position?

To thrive in a 1099 position, you need expertise in your specific field, a strong understanding of self-employment regulations, and the ability to manage your own business operations. Familiarity with accounting software, invoicing systems, and relevant industry certifications can streamline administrative and compliance tasks. Excellent time management, self-motivation, and communication skills help you juggle multiple clients and maintain professional relationships. These skills and qualities are essential as they enable you to operate independently, deliver quality service, and ensure sustained business growth.

What are some common challenges faced by professionals working in 1099 (independent contractor) positions?

Professionals in 1099 positions often encounter challenges such as managing inconsistent income, handling their own taxes and benefits, and maintaining a steady flow of clients or projects. Unlike traditional employees, 1099 contractors are responsible for their own health insurance and retirement planning, which can require additional research and organization. Additionally, they must be proactive in networking, marketing their services, and staying current with industry trends to remain competitive and secure ongoing work.

What is the difference between 1099 Position vs Independent Contractor?

Aspect1099 PositionIndependent Contractor
CredentialsMay require specific certifications depending on the roleOften requires similar certifications, depending on industry
Work EnvironmentTypically project-based or freelance work, flexible hoursSimilar flexible work environment, often self-managed
Employer UsageUsed by companies to classify freelance or temporary workersCommonly used interchangeably with 1099 Position, both refer to non-employee roles

Both 1099 Position and Independent Contractor refer to non-employee roles with similar credentials and flexible work settings. The main difference is that 1099 Position emphasizes the tax classification, while Independent Contractor describes the working relationship. They are often used interchangeably in industry contexts.

How do I become a 1099 position?

To work as a 1099 independent contractor, you typically need to establish your own business entity, such as a sole proprietorship or LLC, and obtain any necessary licenses or permits. You will also need to set up a system for tracking income and expenses, and be prepared to handle self-employment taxes. No specific certification is required, but relevant skills and experience in the field are essential.

What are popular job titles related to 1099 Position jobs in Boston, MA?

For 1099 Position jobs in Boston, MA, the most frequently searched job titles are:

What job categories do people searching 1099 Position jobs in Boston, MA look for?

The top searched job categories for 1099 Position jobs in Boston, MA are:

What cities near Boston, MA are hiring for 1099 Position jobs?

Cities near Boston, MA with the most 1099 Position job openings:

1099 Position jobs near you
Infographic showing various 1099 Position job openings in Boston, MA as of August 2026, with employment types broken down into 45% Full Time, 37% Part Time, and 18% Contract. Highlights an 88% In-person, and 12% Remote job distribution.

Hazmat / Tanker Driver

Lion Freight Systems Inc

Boston, MA • On-site

$2.0K - $3.0K/wk

Full-time

Re-posted 9 days ago

Job description

$2,000-$3,000 | OTR Dry Van & Reefer CDL Drivers Wanted

Job details:
  • Dry van & Reefer trailers.
  • 70-75cpm or 27% of the gross.
  • New automatic trucks (2020-2027).
  • 1099 position with weekly direct deposit.
  • 2-3 weeks out.
  • 24/7 dispatch & driver support.

Requirements:
  • At least 2 years of CDL Class A experience.
  • Valid Medical Card.

Apply today - start tomorrow! Hiring nationwide!