Payroll Specialist

DirectMeds | Remote | Full-Time

Compensation: $75,000–$80,000 annually

Reports to: Head of People

Key Responsibilities

• Manage and process accurate, timely weekly payroll for 500+ employees across multiple entities and states.
• Review existing payroll procedures, identify discrepancies and areas for improvement, and implement effective solutions.
• Develop and maintain standardized payroll processes, checklists, calendars, internal controls, and documentation.
• Investigate and resolve payroll discrepancies involving employee records, timekeeping, benefits, deductions, and HRIS integrations.
• Ensure compliance with federal, state, and local payroll regulations, including multi-state tax withholding and reporting requirements.
• Support payroll setup and compliance requirements as the company expands into additional states.
• Coordinate year-end payroll activities, including W-2 preparation, payroll reconciliations, and required reporting.
• Partner closely with Finance and People Operations to ensure accurate payroll reconciliations, general ledger mapping, and approvals.
• Respond to employee payroll inquiries professionally, accurately, and in a timely manner.
• Continuously identify opportunities to streamline payroll operations, improve accuracy, and reduce recurring errors.

Required Qualifications

• Minimum of 3 years of hands-on payroll processing experience, including multi-state payroll.
• Experience working in a fast-paced, high-growth, or startup environment.
• Demonstrated success improving, rebuilding, or implementing payroll processes and procedures.
• Strong understanding of payroll compliance, tax withholding, deductions, and reporting requirements.
• Experience working with payroll software and Human Resources Information Systems (HRIS).
• Strong analytical, reconciliation, and problem-solving skills.
• Proficiency with Microsoft Excel or Google Sheets.
• Exceptional organizational skills and attention to detail.
• Strong written and verbal communication skills.
• Ability to manage confidential employee and financial information with professionalism and discretion.

Preferred Qualifications

• Experience managing payroll across multiple legal entities.
• Previous experience within the healthcare or pharmacy industry.
• Certified Payroll Professional (CPP) or Fundamental Payroll Certification (FPC).
• Experience implementing payroll controls, process improvements, or system integrations.

Compensation

Annual Salary: $75,000–$80,000, based on qualifications and experience.

Direct Meds is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or veteran status.

About DirectMeds

DirectMeds is a fast-growing healthcare company with over 500 employees across multiple states and legal entities. As we continue to expand, we're focused on strengthening our operations, improving efficiency, and building scalable processes that support our continued growth.

We are seeking an experienced, detail-oriented Payroll Specialist to join our People Operations team. The ideal candidate is someone who takes ownership, thrives in a fast-paced environment, and has a proven track record of identifying payroll discrepancies, improving existing systems, and implementing reliable processes that ensure accuracy, compliance, and efficiency.