Breakaway

Role Description Breakaway is seeking a highly detail-oriented and dependable Payroll Specialist (Contractor) to manage all payroll operations for full-time employees and contractors through Rippling. This role will be responsible for processing semi-monthly payroll on the 15th and last day of each month, ensuring accuracy, compliance, and timely payments across the organization. The Payroll Specialist will work cross-functionally with People Operations to: - Maintain payroll records - Support employees onboarding and off-boarding - Manage contractor payments - Ensure compliance with payroll regulations The ideal candidate is organized, proactive, and experienced in handling payroll in a fast-paced, high-growth environment. Responsibilities - Process semi-monthly payroll for full-time employees and contractors through Rippling - Ensure accurate payroll calculations, including wages, bonuses, reimbursements, deductions, and contractor payments - Maintain and update payroll records, employee information, and compensation changes - Review and verify payroll data, timesheets, and approvals prior to payroll submission deadlines - Ensure compliance with federal, state, and local payroll regulations and tax requirements - Coordinate payroll reporting, reconciliations, and year-end activities, including W-2s and 1099s - Respond to payroll-related questions from employees and contractors in a timely and professional manner - Partner with HR to support payroll operations and process improvements - Support with contractor onboarding in Rippling - Maintain confidentiality and accuracy when handling sensitive employee and payroll information Qualifications - 3+ years of payroll processing experience - Hands-on experience using Rippling payroll systems - Experience processing payroll for both W-2 employees and 1099 contractors - Familiarity with semi-monthly payroll schedules - Strong understanding of payroll compliance, taxes, and labor regulations - Excellent attention to detail and organizational skills - Ability to manage confidential information with discretion - Strong communication and problem-solving skills - Proficiency in Excel and payroll reporting - Experience in startup, entertainment, events, or high-growth environments is a plus Details - Contractor / 1099 position - Flexible schedule aligned with payroll cycles (10 hours per week) - Competitive hourly or contract-based compensation based on experience