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Independent Contractor Payroll Jobs in Addison, IL

SharpPencil AI

Be Seen First

Sales Representative

Chicago, IL · Remote

$200K/yr

This is a purely Commission-Driven, 1099 Independent Contractor position that offers high earning ... You get paid on any service the client adds (payroll, merchant services, etc.), even if they add it ...

HOA Talent

Compliance Coordinator

Chicago, IL · Hybrid

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

About TCC The CAM Collective ("TCC") is a national network of independently operated community ... The Compliance Coordinator owns business registrations, payroll registrations, licenses, and ...

HOA Talent

Compliance Coordinator

Chicago, IL · On-site

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

About TCC The CAM Collective ("TCC") is a national network of independently operated community ... The Compliance Coordinator owns business registrations, payroll registrations, licenses, and ...

DivIHN

Compensation Consultant - 2 Openings

Lisle, IL · On-site

Compensation work directly affects payroll costs, employee equity, legal compliance, and leadership ... The contractor must be able to work independently, resolve complex issues, and provide high-quality ...

Oswald Companies

Client Manager - Project Risk

Chicago, IL

$84K - $107K/yr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Oversees contractor enrollment, compliance tracking, documentation review, and communication with ... Ensures timely coordination and management of payroll audits, reporting, safety performance metrics ...

VIVA USA INC

Compensation Consultant

Lisle, IL · On-site

Compensation work directly affects payroll costs, employee equity, legal compliance, and leadership ... The contractor must be able to work independently, resolve complex issues, and provide high-quality ...

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Independent Contractor Payroll information

See Addison, IL salary details

$15

$27

$39

How much do independent contractor payroll jobs pay per hour?

As of Aug 19, 2026, the average hourly pay for independent contractor payroll in Addison, IL is $27.45, according to ZipRecruiter salary data. Most workers in this role earn between $22.64 and $30.82 per hour, depending on experience, location, and employer.

What is an independent contractor payroll?

An Independent Contractor Payroll job involves managing payments, tax compliance, and financial records for independent contractors. Unlike traditional employees, independent contractors are responsible for their own taxes, so payroll specialists ensure proper classification and issue 1099 forms instead of W-2s. This role also involves verifying contracts, tracking hours or project-based earnings, and ensuring timely payments. Compliance with labor laws and tax regulations is essential to avoid misclassification risks.

What are the key skills and qualifications needed to thrive in independent contractor payroll?

To thrive as an Independent Contractor Payroll professional, you need a strong understanding of payroll regulations, independent contractor status, and tax compliance, often backed by experience in accounting or payroll administration. Familiarity with payroll processing software, tax filing platforms, and sometimes certifications such as CPP (Certified Payroll Professional) are highly beneficial. Detail orientation, effective communication, and problem-solving skills help you manage complex payment scenarios and ensure accurate records. These competencies are crucial for delivering timely, compliant payroll services to independent contractors and maintaining trust with clients or business partners.

What are some typical challenges faced in independent contractor payroll roles?

Professionals in Independent Contractor Payroll often navigate complex compliance requirements, such as distinguishing between employee and contractor classifications and adhering to varying state and federal tax rules. A key challenge is ensuring timely and accurate payments while keeping up with ever-changing tax forms and reporting deadlines. Additionally, managing clear communication with contractors and addressing their payment or documentation questions is essential. Staying organized and proactive helps mitigate these challenges, making you a valuable asset to any business working with independent contractors.

What are the most commonly searched types of Payroll jobs in Addison, IL?

The most popular types of Payroll jobs in Addison, IL are:

What job categories do people searching Independent Contractor Payroll jobs in Addison, IL look for?

The top searched job categories for Independent Contractor Payroll jobs in Addison, IL are:

What cities near Addison, IL are hiring for Independent Contractor Payroll jobs?

Cities near Addison, IL with the most Independent Contractor Payroll job openings:

Independent Contractor Payroll jobs near you
Infographic showing various Independent Contractor Payroll job openings in Addison, IL as of August 2026, with employment types broken down into 1% As Needed, 74% Full Time, 19% Part Time, and 6% Contract. Highlights an 91% Physical, 2% Hybrid, and 7% Remote job distribution, with an average salary of $57,089 per year, or $27.4 per hour.

Sales Representative

SharpPencil AI

Chicago, IL • Remote

$200K/yr

Full-time

Re-posted 13 days ago

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Job description

About the Role: Sharp Pencil is a rapidly growing startup revolutionizing the financial services industry. We utilize advanced AI technology to provide third-party bookkeeping, accounting, tax preparation, and business consulting services to small and medium-sized businesses.

We are seeking entrepreneurial-minded Sales Representatives to join our team nationwide. This is a purely Commission-Driven, 1099 Independent Contractor position that offers high earning potential through a lucrative residual income model. You will have the freedom to work from home, set your own schedule, and sell without territory restrictions.

Why Join Us?

  • High Commission Rate: Earn a flat 20% commission on all billing.
  • Residual Income: Build a book of business! You earn commission every month the client pays their bill, creating cumulative income that grows over time.
  • Total Account Commission: You get paid on any service the client adds (payroll, merchant services, etc.), even if they add it later without your direct involvement.
  • Growth Potential: As a new company, we offer the unique opportunity to grow your career alongside the business.
  • Flexibility: 100% remote, home-based, with no protected territories—sell to business owners anywhere in the U.S.

Responsibilities:

  • Prospect and contact small to medium-sized businesses to introduce Sharp Pencil’s AI-driven bookkeeping and financial solutions.
  • Present and sell company services to new and existing customers, effectively communicating the value of outsourcing financial tasks.
  • Reach agreed-upon sales targets to maximize personal revenue.
  • Manage the sales cycle from initial contact to closing the deal.
  • Resolve customer inquiries and offer solutions to drive revenue.
  • Set follow-up appointments to keep customers aware of the latest developments and service add-ons.

Qualifications:

  • Self-Starter: Must be disciplined and motivated to work independently in a remote environment.
  • Previous experience in sales, business development, or customer service (B2B sales experience is a plus).
  • Ability to build rapport with clients and maintain long-term professional relationships.
  • Strong negotiation skills and a "hunter" mentality.
  • Familiarity with CRM platforms and comfortable using technology.
  • Deadline and detail-oriented.

Compensation:

  • Type: 1099 Independent Contractor.
  • Pay Structure: 100% Commission-Only.
  • Earning Potential: Uncapped.
    • Note on Earnings: Income is cumulative. While first-year earnings may vary as you build your pipeline (e.g., $60k–$120k), the residual model allows for significant jumps in subsequent years (e.g., $200k+) as your client base renews and expands.