Whether you’re hiring a freelancer or a contractor to work remotely, there are some things you need to know about how to pay remote contractors. 

Today’s economy demands that small businesses stay agile and flexible. Outsourcing is more accessible than hiring full- or part-time employees and an excellent option for a company that needs more hands but doesn’t require full-time employees. 

As the outsourcing trend gains popularity, businesses are starting to realize how hiring remote contractors means not worrying about benefits, payroll taxes, office space, and other overhead costs.

But it’s not all smooth sailing. How to pay remote contractors can be tricky if you’re new to outsourcing.

What is a Remote Contractor, and Why are They Different Than Employees?

A remote contractor is a person who works for a company but doesn’t have an office or other physical presence. They are self-employed and can work from anywhere, like a home office or a coffee shop. Most companies hire remote contractors for individual projects or tasks, but some also hire them regularly.

Remote contractors differ from traditional employees because they’re not on the payroll, don’t get employee benefits, and are responsible for declaring their own earnings and filing taxes. 

Remote contractors can be especially valuable if you need an expert for an important project or task but don’t want to invest in onboarding or training for a new employee. This is a common practice for one-off projects or if the activity doesn’t equate to a full-time resource. Another typical instance is needing someone for specialized work that requires more expertise to support your regular employees.

Essential Factors for Knowing How to Pay Remote Contractors

The number of remote contractors is growing. Technology has enabled people to work from anywhere, people around the globe are becoming more and more skilled, and companies realize the opportunities hiring remote contractors presents.

But if you’re going to hire and maintain accountability with remote contractors, there are a few things you need to know. 

Backup Withholding Taxes

Many states require employers to withhold taxes from independent contractors within their borders. This practice is often referred to as backup withholding. Some states require it, and some don’t. Understanding your state’s rules before you start working with any remote contractors can save headaches on the back end.

If not required by law, tax filing options can help prevent you from being subject to backup withholding penalties. Where required by law, learn how much tax to withhold and on what schedule (monthly or quarterly).

They’ll Need to Fill Out a W-9 Form

The W-9 form helps collect:

  • The contractor’s taxpayer identification number,
  • Certification,
  • Where they will declare their tax status (if any). 

Ensure the contractor has provided their Social Security (or EIN – employer identification) number so you can match it up with the information on their W-9 form (if they didn’t send one along with their proposal).

Before doing anything else, you must ensure that your contractor has filled out this form. The IRS even provides an online version so companies can access it anytime they need it.

1099 Form

If you hire remote workers, you may be required to send them a 1099 form. This form is for self-employed individuals and independent contractors who are not your company’s employees. The IRS uses this form to track all payments made to these individuals over the year.

1099 forms are documents that report income to the IRS and help contractors report their earnings on their taxes. Any contractor you paid $600 or more (including salary, commissions, bonuses, etc.) must receive these forms shortly following each calendar year. The form also informs the IRS how much you paid them over the year.

Create Payment Terms

When and how will you pay your contractors? Will payments be made weekly, monthly, or in installments based on project milestones? 

When deciding on payment terms, consider the amount of work involved and how long it will take for you to receive results from the contractor. 

How you should pay depends on your cash flow and the type of work. Paying installments over time may make sense for high-value projects, and you can anchor these installments to periods, delivery of certain work packages, or specific milestones.

In most cases, however, your cash flow is best served by paying a lump sum at the end of a job.

Your business’s cash flow is often the most significant factor in determining how much money you should offer. But don’t neglect your contractors’ needs. Can your contractor afford to wait until a lengthy project is complete before receiving payment? Could you? 

Agreeing on a payment scheme that works for you is one aspect of enabling the contractor to do good work. 

Still Struggling with How to Pay Remote Contractors?

Savvy entrepreneurs want to get projects done quickly and efficiently, which is why people opt for hiring remote contractors. 

But sorting out how to pay remote contractors can be a complex question. 

Some tools, like payroll software, can help. For example, they might allow you to automatically track contractor hours and generate paycheck stubs and 1099s for each worker. But for these to work well, you typically need a basic understanding of what should happen in the process.

If you don’t know where to start when it comes to how to pay remote contractors, Founder’s can also help. Contact us today, and our team of experts can get you moving in the right direction.

Curt Mastio
Post by Curt Mastio
Jun 13, 2024 9:25:16 AM
Curt Mastio started Founder’s CPA in 2017 and currently serves as the Managing Partner of the firm. After obtaining both his Bachelor’s and Master’s degrees in accounting from the University of Illinois in Urbana-Champaign Curt started his career in Big Four public accounting. Shortly thereafter Curt served as the Chief Financial Officer of Storage Squad began his stint as an Adjunct Instructor at Northwestern University’s Farley Center for Entrepreneurship and has been teaching Accounting & Finance to undergraduate students for 6+ years. In his current role Curt oversees strategy, operations, and business development at Founder’s CPA. Further, Curt has experience working directly with 200+ startups and small businesses providing accounting, tax, and outsourced CFO services. His industry expertise lies in the SaaS, Blockchain, Marketplace, and Fintech industries. He has served as a key advisor working directly with startups that range from pre-revenue to companies generating over $30 million dollars a year in revenue. Lastly, he serves a key role working directly with the firm’s clients that have collectively raised over $200 million in venture capital funding to date. Curt is also an active advisor, mentor, and investor in the startup ecosystem. He has facilitated numerous workshops, webinars, and presentations to incubators and other startup-centric organizations. He is also an active mentor for Techstars in both Chicago and Iowa. Outside of his daily professional duties Curt is actively involved with Beat the Streets Chicago and was a founding member of its Young Professionals Board. His efforts in both leadership and community involvement were recognized when he was awarded the Illinois CPA Society’s Outstanding Young Professional Leadership Award in 2020. He was also a panelist at their annual conference in 2022 where he spoke about his experiences starting and operating a public accounting firm. He maintains an active Certified Public Accountant designation that he obtained in 2014. Outside of work, Curt can be found spending time with his friends & family including his dog Rufus. His hobbies include golf, boating, cooking, reading, and attending sporting events & concerts.