Remote Work and Payroll:
10 Challenges and Solutions for Employers in the US

Written by Asim Qureshi
By Asim Qureshi, CEO Jibble

Hi, I’m Asim Qureshi, the CEO and co-founder of Jibble, a cloud-based time and attendance software. I have several years of experience in building and scaling software products and teams across various industries and markets. Before I founded Jibble, I worked as a VP at Morgan Stanley for six years. I’m passionate about helping businesses improve their productivity and performance through smart time management practices.


Remote work has become a prevalent trend in the modern workforce, offering flexibility and convenience for both employees and employers. However, managing payroll for remote employees presents a unique set of challenges for businesses. 

From tax compliance to remote work policies, this article explores the complexities associated with remote work payroll management and provides solutions for employers to navigate these challenges effectively.

This Article Covers:

What Are the Risks of Mismanaging Remote Employees' Payroll?

Failing to manage remote employees’ payroll accurately can lead to various risks and negative consequences for both employees and employers. Here are some key risks:

  • Legal and Regulatory Non-Compliance: Inaccurate payroll can result in non-compliance with federal, state, and local labor laws, including minimum wage, overtime, tax withholding, and labor rights regulations. Non-compliance can lead to costly penalties, fines, and legal disputes.
  • Audit Triggers: Payroll discrepancies may trigger tax audits or labor audits by government agencies, increasing the scrutiny and potential for further penalties.
  • Operational Disruptions: Dealing with payroll errors and correcting them can disrupt HR and finance operations, diverting time and resources away from other critical tasks.
  • Tax Compliance Issues: Incorrect tax withholding and reporting can lead to issues with tax authorities. Employers may be held responsible for unpaid taxes, penalties, and interest. Failure to accurately report remote employees’ income can also result in tax audits.
  • Loss of Trust and Employee Retention: When employees experience payroll errors, it erodes trust in the employer. This can lead to higher turnover rates as employees may seek more reliable job opportunities elsewhere, impacting talent retention efforts.
  • Reputational Damage: Payroll mistakes, especially when they become public knowledge, can harm a company’s reputation. Negative publicity may deter potential clients, partners, and investors.
  • Financial Costs: Correcting payroll errors may involve additional administrative costs, such as processing corrections and reissuing paychecks. It can also result in financial losses if overpayments need to be recovered.

A person working remotely on their laptop. Photo by Windows on Unsplash

10 Challenges and Solutions to Running Payroll for Remote Employees

Consideration #1: Compensation Compliance with Labor Laws

Employers with remote workers in multiple states must navigate a web of state-specific payment-related laws and tax regulations. US labor laws, including minimum wage and overtime, still apply to remote workers. Each state may have unique rates as well as tax requirements and, in general, when employees engage in remote work, they are immediately subject to the laws and regulations of the state in which they are working. This can potentially expose employers to a range of state-specific benefit programs and mandates, including requirements related to paid leave, minimum wage, mandatory disclosures, diverse wage statement criteria, and more.

For instance, in California, employees are entitled to receive overtime pay if they work more than eight hours in a day, and double time if they exceed 12 hours in a single day. Additionally, California mandates paid sick leave, and meal and rest break premiums must be calculated using an employee’s regular rate of pay. Further, New York Department of Labor officials have clarified their stance on work arrangements that cross state lines, emphasizing that all New York employment laws become applicable immediately if employees engage in remote work within the state. Unlike tax withholding compliance, Wage and hour laws do not provide for any threshold related to temporary or part-time presence that would exempt an employer from compliance.

Key Solutions:

  • Policy Standardization: While state laws may vary, employers can consider establishing standardized policies that meet or exceed the requirements of the most stringent state regulations. This approach ensures consistent compliance across all states and reduces the administrative burden of tracking and managing state-specific policies.
  • Flexible Compensation Structures: Consider adopting compensation structures that can adapt to various state requirements. This might involve implementing systems that allow for easy adjustment of pay rates, overtime calculations, and benefit accruals based on the specific state regulations applicable to each remote worker.
  • Technology Solutions: Utilize technology solutions that assist in managing compliance. There are software tools and platforms available that can help automate payroll calculations, track hours worked, and ensure that remote workers are paid in accordance with state-specific regulations. These tools can significantly reduce the risk of errors and streamline compliance efforts.
  • State-Specific Onboarding: When hiring remote workers, consider customizing the onboarding process to address state-specific requirements. This may include providing state-specific employment agreements or disclosures to ensure compliance from day one.
  • Compliance Review: To navigate the diverse landscape of state-specific regulations, employers should conduct a comprehensive compliance review. This involves a careful examination of each state’s labor laws, paid leave requirements, minimum wage rates, and wage statement criteria. This proactive approach allows employers to identify the specific regulations that apply to remote workers in each state.

Consideration #2: Method of Compensating Remote Employees

  • Paying Remote Workers in the US: When it comes to disbursing payments to remote workers in the US, employers have a variety of choices available, including direct deposit, checks issued by payroll service providers, and utilizing payroll apps or services like PayPal or Venmo. An existing payroll service for the on-site team typically would offer a solution for handling payments to remote employees as well.
  • Paying Remote Workers Overseas: While many of the same payment methods can be applied for international remote teams, it’s essential to consider two important factors. First, it’s advisable to review the international bank fees associated with fund transfers. These fees can sometimes be quite substantial, often exceeding $30 per transaction, which may not be the most cost-effective option. Secondly, employers must not overlook the impact of international exchange rates. International employees may experience a decrease in their earnings once their portion is converted into their local currency. Additionally, banks and other payroll services might impose significant fees to cover the expenses related to currency exchange, further increasing the overall costs

Key Solutions:

Payment Solutions for Remote Workers in the US:

  • Streamlined Payroll Services: Utilize payroll service providers that offer integrated solutions for both on-site and remote employees. This ensures consistency and efficiency in payroll processing. Ensure that the chosen provider supports various payment methods, including direct deposit and electronic payment options. 
  • Comprehensive Payroll Software: Invest in robust payroll software that can manage payments to remote workers seamlessly. Look for software that offers secure direct deposit capabilities, supports multiple payment methods, and allows for easy customization to meet individual state requirements. 
  • Transparent Communication: Maintain open communication channels with remote workers regarding their preferred payment methods. Seek their input and accommodate their preferences within the framework of applicable payment options. 

Payment Solutions for Remote Workers Overseas:

  • Evaluate Payment Providers: Research international payment providers and banks to identify cost-effective options for fund transfers. Compare transaction fees and currency conversion rates to select the most favorable solution for both the employer and the remote worker.
  • Local Currency Accounts: Consider opening local currency accounts in the countries where you have international remote workers. This allows you to pay employees in their local currency, reducing the impact of exchange rate fluctuations and associated fees.
  • Payment Frequency: Explore options for less frequent payments to minimize transaction costs. For example, make monthly payments instead of weekly transfers if feasible for your international remote team.
  • Advance Planning: Plan payment schedules in advance to allow time for fund transfers and currency conversions. Avoid last-minute transactions to prevent rushed and costly transfers.
  • Currency Exchange Management: Employ specialized currency exchange services that offer competitive rates and lower fees compared to traditional banks. These services can help optimize currency conversion and reduce overall costs.
  • Reimbursement Policies: Implement clear reimbursement policies for transaction fees incurred by remote workers when receiving payments. Some companies choose to cover these fees to ensure that employees receive their full earnings.
  • Regular Review: Continuously monitor the efficiency and cost-effectiveness of your international payment methods. Periodically reassess providers and explore new options as the financial landscape evolves.

Consideration #3: Taxes and Remote Workers in the US

Employers deduct state and local income taxes based primarily on the location where an employee carries out their duties, which is typically their physical work site. In certain cases, the employee’s place of residence may also come into play as a secondary factor. Reciprocity agreements between states exist in some instances, allowing for tax withholding in a single state, which can be advantageous. However, it’s worth noting that these agreements are only in place in less than half of the states.

When it comes to handling taxes for remote workforce, the key factors to consider are the classification of the employees and their respective locations.

  • Taxes for Remote Employees in the US: In general, when paying a remote employee, employers are responsible for local taxes in the state where the employee is based. If the remote employee happens to work in the same state where the company is registered, they’ll need to withhold state income taxes and pay state unemployment insurance (SUI) tax in that state. In some cases, employers might also have to withhold local income tax from their paychecks. In such a scenario if the remote employees are scattered across different states, the company must register with the tax agencies (state and possibly local) in each state where they have remote employees. It might also be necessary to register with the labor/unemployment agencies in these locations. Consequently, employers would be obligated to withhold taxes according to the tax laws of each state where the employees are based. For instance, if a company, based in Washington, hires a remote employee in Florida, it will need to adhere to Florida’s tax regulations and labor laws.
  • Taxes for Remote Workers in Other Countries: Hiring and paying remote workers in different countries presents unique challenges. It’s typically more straightforward to hire remote employees from countries where the company is already established. Most countries will require the employer to establish a local branch of the company within their borders. Then, the employer would need to comply with all local labor laws, including minimum wage and benefits, for the remote team members in that country. This complexity is why international candidates are often engaged as contract employees rather than full-time company employees. Once they register as self-employed business owners or freelancers, they take on the responsibility of managing their international tax obligations. 
  • Taxes for Contractors: Although contract employees handle their own tax matters, the company still has some responsibilities. Employers should have their contractors complete a W-9 form, which officially requests their Taxpayer Identification Number and Certification. This information is necessary for the next step. The company needs to complete a 1099 form for each contractor who has been paid more than $600 during the year. This form provides the IRS (Internal Revenue Service) with details on how much the employer paid to these non-employee workers. One copy goes to the IRS, and another is sent to the freelancer.

Key Solutions:

  • Regularly Update Employee Information: Keep track of where your remote employees are working and update their tax information accordingly.
  • Update Payroll Policies: Regularly review and update your organization’s payroll policies and procedures to reflect changes in tax laws and regulations. Ensure that these policies are accessible to all employees and contractors so they can reference them when needed.
  • Technology Integration: Invest in payroll and time tracking software that can integrate with various locations and comply with state tax regulations. Modern payroll solutions can automatically calculate taxes based on the employee’s location and generate accurate paychecks. A number of payroll software can automatically calculate and withhold taxes based on the employee’s work location, simplifying the process and reducing the risk of errors. You may want to check out our selected 6 Best Apps to Simplify your Payroll Process in the US
  • Outsource Payroll: Consider outsourcing payroll to experts who can manage multistate tax compliance.
  • Consult with a Tax Professional: Seek legal counsel or HR experts with expertise in multistate compliance to navigate the complexities of varying state regulations. Seek guidance from a tax expert or CPA who specializes in multi-state tax compliance to ensure your business complies with all relevant state tax laws. 
  • Document and Maintain Records: Maintain detailed records of all payroll-related activities, including tax filings, employee classifications, and payment records. Proper documentation can serve as evidence of compliance in case of audits or legal disputes. Implement robust record-keeping practices to ensure accuracy and transparency.

Consideration #4: Tracking Work Hours and Productivity

Monitoring remote employees’ work hours and productivity can be challenging, particularly that the employees are working in different timezones and with varying schedules, leading to potential payroll inaccuracies or disputes. Verifying remote employees’ work hours, especially for roles without direct supervision necessitates accurate time tracking. This is crucial for calculating wages, overtime, and compliance with labor laws. Implementing effective time tracking solutions is essential for maintaining payroll accuracy.

Key Solutions:

  • Regular Check-Ins: Schedule regular check-in meetings with remote employees to discuss their tasks, progress, and any obstacles they may encounter.
  • Outcome-Based Performance Metrics: Focus on outcome-based performance metrics rather than micromanaging work hours. Evaluate employees based on results and achievements rather than the number of hours worked.
  • Time Tracking Tools: Implement time clock software or applications that allow employees to log their work hours accurately. These tools can provide transparency and accountability, ensuring compliance with labor laws, and can also help managers monitor employee productivity.

Consideration #5: Employee Classification

The categorization of remote employees plays a crucial role in determining the benefits they are eligible for, as governed by federal and state regulations. While federal law determines the exempt or nonexempt status of an employee, employers hold the responsibility of classifying employees into categories such as full-time, part-time, or temporary. To maintain clarity and consistency, employers should articulate precise definitions of these employment classifications within their employee classification policy. Accurate employee categorization is essential to ensure that employees receive their entitled benefits, including social security and healthcare coverage, in compliance with both federal and state laws.

Accurately classifying remote workers as either employees or independent contractors is crucial. Full-time remote employees work all their hours from home and fall under the employee classification. Employers typically set full-time hours, with many defining it as 35 to 40 hours per week. Non-exempt employees may be eligible for overtime pay if they work beyond 40 hours per week. Remote independent contractors, on the other hand, work independently for a company and have flexibility in setting their rates and hours. They are often hired for specific projects, like website development.  Misclassification can lead to legal issues and tax penalties. 

Further, exempt and non-exempt are different employee classifications. Exempt employees are usually salaried and not eligible for overtime pay for working more than 40 hours per week. In contrast, non-exempt employees receive hourly wages and may qualify for overtime pay.

Key Solutions:

  • Stay Updated on Employee Classification Criteria: Ensure that you are always aware of the key elements that differentiate employees and their categorizations, whether they are independent contractors or employees, exempt or non-exempt will depend on these features and may change with time and across state. Certain updates might make employees no longer eligibile for certain categories which is why staying informed is crucial.
  • Create a Consistent Classification Assessment Process: Establish a clear and uniform method for evaluating employee categories to ensure legal compliance and internal consistency. Develop a comprehensive employee classification policy that will guide your classification assessments for new hires and provide regular reviews to maintain accuracy. Thoroughly document this process to support your organization in case of an audit.
  • Ensure Professional Drafting of Employment Contracts: Employment contracts should be comprehensive, outlining the worker’s duties, payment structure, and relevant timeframes. However, the contract alone doesn’t determine employee categories; factors like payroll status also contribute.

Consideration #6: Benefits Administration

Employers often need to choose appropriate benefits for a remote workforce, taking into account factors like budget, legal obligations, and employee preferences that may impact payroll. These benefits can include core offerings like health insurance and retirement plans, as well as optional ones such as wellness programs, paid time off, flexible schedules, learning opportunities, and employee assistance programs. Additionally, employers must consider specialized benefits tailored to remote employees, such as home office equipment, internet subsidies, coworking space memberships, travel allowances, or relocation assistance. 

Health insurance networks, which are typically tied to specific geographic regions, should not be assumed to automatically cover remote employees in new areas. Unemployment benefits can be complex when multiple states are involved. HR managers must assess claims and ensure correct filing, considering the distinct requirements of each state. Local laws add another layer of complexity, encompassing various areas like employee benefits, medical regulations, wage laws, and state disability programs. 

Key Solutions:

  • Consult Benefit Providers: Work closely with benefits providers to ensure remote employees have access to the same benefits as in-office staff.
  • Simplify Benefit Enrollment: Communicate benefit options clearly and provide remote-friendly enrollment processes. Prioritize benefits that are meaningful, accessible, and beneficial to all employees, regardless of their work location.
  • Adjust Your Process to Cover Benefits: Implement appropriate processes and systems for administering and tracking benefits effectively to ensure that your benefits align with the laws and regulations in the countries and regions where your employees are located. 
  • Consult Legal Counsel: Seeking legal counsel with expertise in employment law and remote work compliance can be invaluable. Legal professionals can provide guidance on how to align your remote work policies with the laws of each state where your employees are based. They can help you understand the nuances of different state regulations and ensure your policies are in compliance.
  • Employee Education: Remote employees should be educated about the employment laws and regulations that apply to their specific location. This includes informing them about their rights, such as overtime pay or paid sick leave entitlements, based on their state of work. Providing clear information can help employees understand their rights and prevent misunderstandings.

Consideration #7: Payroll and Data Security

A key issue for organizations in the remote work setting is protecting sensitive payroll information. As employees operate from various locations, the potential for data breaches and unauthorized access grows. Remote work environments are alluring targets for cybercriminals seeking payroll system vulnerabilities. Payroll fraud, involving unauthorized changes or fake accounts, poses financial and reputational risks. Cyberattacks like phishing and ransomware exacerbate payroll security concerns. Remote work often involves the transmission and storage of sensitive company and customer data. Employers must ensure that remote employees follow robust cybersecurity practices to protect against data breaches and privacy violations.

Additionally, achieving adherence to data protection regulations presents an added challenge in remote work environments. Organizations must maneuver through an intricate landscape of laws and rules, such as the General Data Protection Regulation (GDPR) in the European Union or the state-specific California Consumer Privacy Act (CCPA) in the United States. Remote work also introduces extra complexities regarding data location and international data transfers.

Key Solutions:

  • Educate Your Employees: Educate remote employees on cybersecurity best practices, including password management and safe handling of sensitive data, and provide comprehensive training to employees on data protection regulations.
  • Invest in Technology: Invest in secure and reliable technology tools for remote work such as encryption techniques, firewalls, multi-factor authentication,  collaboration platform, antivirus software, and secure virtual private networks (VPNs).
  • Evaluate and Update Your Payroll Processes: Assess payroll procedures, revise their privacy policies, and set clear guidelines for sensitive data handling, secure document storage, and data-sharing protocols.
  • Add Communication Layer: Communicate data use with your remote employees, and protection measures, and obtain consent. 

Consideration #8: Employee Expense Reimbursement

Determining which work-related expenses remote employees are entitled to and how to reimburse them can be a challenge. Employers need policies in place to address expenses such as home office equipment, internet costs, and utility bills. In recent years, several employees filed lawsuits against their employers for not reimbursing remote work expenses. Companies like Wells Fargo, Liberty Mutual Insurance, Visa, Oracle, Bank of America, and even Amazon have faced legal action from employees in California over unpaid remote work costs.

Certain US states mandate that employers reimburse employees solely for essential expenses. The specific criteria for determining what qualifies as essential can be somewhat subject to interpretation, but generally, state laws define essential expenses as those required for employees to fulfill their job responsibilities. Typically, if an employee voluntarily opts to work remotely, these expenses may not be categorized as essential. However, if your entire organization operates remotely, either on a full-time or part-time basis, these expenses would be considered essential for your employees to effectively carry out their job duties.

Under federal law, employers are not obligated to provide reimbursement for employee work-related expenses. However, it’s essential to note that the Fair Labor Standards Act (FLSA) mandates employers to reimburse employees for these expenses if they result in the employee’s earnings falling below the federal minimum wage. Furthermore, employers are prohibited from compelling employees to cover costs associated with the use of employer-provided equipment if such expenses would reduce their earnings below the minimum wage or infringe upon overtime compensation requirements. These federal regulations pertain to all types of business-related expenses. It’s important to emphasize that there are no federal directives specifically addressing remote work-related expenses. Nonetheless, certain states have implemented legislation obligating employers to compensate employees for any deemed “necessary” work-related expenditures.

Key Solutions:

  • Expense Policies: One effective approach to managing remote work expense reimbursements is to establish a formal written policy within your organization. This policy should clearly define which expenses are eligible for reimbursement and should encompass any legally mandated reimbursements for employees.
  • State-Specific Compliance: Stay informed about state-specific reimbursement laws and requirements, as they can vary significantly. Employ legal counsel or compliance experts to ensure your policies comply with the laws in each state where your remote employees are based.
  • Fair Compensation Practices: Adhere to federal regulations, particularly the Fair Labor Standards Act (FLSA), when calculating reimbursements. Ensure that reimbursable expenses do not cause employees’ earnings to fall below the federal minimum wage, and refrain from requiring employees to cover costs that would violate minimum wage or overtime compensation rules.
  • Regular Policy Review: Continuously review and update your expense reimbursement policies to adapt to changes in state laws, employee needs, and evolving remote work dynamics. This proactive approach helps maintain compliance and aligns policies with best practices

Consideration #9: Temporary Presence

Certain remote employees may consistently change their location of work, traveling from state to state or even internationally, which causes variation in their tax obligations. In such cases, employers need to adhere to well-established, yet intricate laws and guidelines that specify the duration an employee can temporarily stay in a state for work-related reasons before the employer becomes obligated to deduct income tax. When an employer is liable for tax withholding, it means that if the employer fails to withhold tax from the employee’s wages, the state can enforce tax collection from the employer. These short-term presence regulations vary significantly and may be based on factors such as the number of days spent in the state (e.g., 14 or 30 days), a specific earnings threshold, or a combination of these criteria.

Key Solutions:

  • Employee Mobility Data: Regularly collect and analyze data on the movement of remote employees across states. This proactive approach allows employers to anticipate tax obligations and make necessary adjustments.
  • Auditing and Documentation: Establish rigorous auditing processes and maintain detailed records of employee work locations and related tax calculations. This documentation will be invaluable in case of audits or disputes.
  • Tax Software Integration: Invest in tax software that can automate and streamline the tax withholding and reporting process for multi-state employees. This can help reduce the administrative burden and enhance accuracy.
  • Effective Tracking: Implement a robust system for tracking the number of days or income thresholds that trigger tax liability in various states. This system should be integrated into payroll or HR software to ensure accuracy and compliance.
  • Transparent Communication: Clearly communicate with remote employees about the potential tax implications of their work location and the employer’s responsibilities. This transparency helps in managing expectations and avoiding surprises at tax time. 

Consideration #10: Established Presence in a State

A significant factor to consider, particularly when employees are working across different states, is the potential impact on business-related taxes. Even if just a single employee is working within a state, it can trigger various state corporate or business activity taxes. In essence, if an employer didn’t previously have an established presence in a state but one employee begins working there, this can lead to entirely new obligations for registration and tax responsibilities. This may involve registering with the secretary of state and relevant tax authorities, designating a registered agent address, and fulfilling obligations related to corporate and business activity taxes, sales taxes, and employment taxes, including employee withholdings. Additionally, there might be requirements for state and local licenses and business permits to address.

Key Solutions:

Proactive State Tax Assessment: Employers should conduct a thorough assessment of the potential tax implications before allowing employees to work in different states. This assessment should encompass the following steps:

  1. State Nexus Analysis: Determine whether the employer’s activities within a state create a “state nexus” or sufficient connection to trigger tax obligations. Understand the specific rules in each state, as they can vary significantly.
  2. State Registration: If necessary, register the business with the secretary of state and relevant tax authorities in states where remote employees are located. Comply with state-specific registration requirements, which may include appointing a registered agent.
  3. Tax Withholding Compliance: Understand the state’s rules regarding income tax withholding for remote employees. Ensure proper withholding and reporting procedures are in place to comply with state tax requirements.
  4. Business Activity Taxes: Be aware of state-specific business activity taxes, such as franchise taxes, gross receipts taxes, or sales taxes. Determine whether these taxes apply based on your remote workforce and establish mechanisms for compliance.
  5. Licensing and Permits: Research state and local licensing and permit requirements that may apply to your business activities in different states. Ensure timely application and compliance.
  6. Ongoing Monitoring: Continuously monitor changes in state tax laws and regulations that could impact your tax obligations. Be prepared to adapt and adjust your tax compliance strategies accordingly
  7. Documentation: Maintain meticulous records of all tax-related activities, registrations, filings, and payments. Comprehensive documentation will be essential for audits and compliance verification.
  8. Integration with Payroll and Accounting: Integrate your payroll and accounting systems to streamline tax withholding, reporting, and remittance processes across multiple states.

Final Thoughts

Managing payroll for remote employees demands proactive strategies and adherence to legal and administrative requirements. Employers must prioritize tax compliance, establish robust remote work policies, track work hours and productivity effectively, and ensure employee benefits compliance.

By implementing these solutions, businesses can successfully navigate the challenges associated with remote work payroll management and create a seamless remote work experience for their employees. If you need to learn more about payroll in general, check out our Step-by-Step Guide to Running US Payroll. Alternatively, if you already have a system in place, you may find these 10 Tips to Streamline your Payroll in the US useful.