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