Payroll Specialist (Contractor)

Who We Are Breakaway Group is a premier multimedia company for entertainment and music festivals. We have the largest independent touring music festival in North America, spanning 13 cities over 9 months. With a focus on underserved markets, Breakaway is bringing a premium 2‑day EDM/Pop festival experience, featuring an ever‑changing lineup of top artists, to where consumers live, work, and play. The Role 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, and 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 #J-18808-Ljbffr Breakaway