Part-Time Payroll & Benefits Specialist (US/Canada)

flyover-chicago; Chicago (IL); Hybrid; USD 32,000 - 36,000; Part time

Job summary

Flyover Attractions in Chicago, IL seeks a part-time payroll and benefits specialist to support our People and Finance teams, handling payroll for US and Canada and benefits administration.

This 20-hour-per-week role offers hybrid work with occasional on-site presence, and collaboration across Canadian and US locations.

You’ll own day-to-day payroll cycles, navigate benefits, and assist with light accounting tasks as needed.

Qualifications

• 3+ years of hands-on payroll and/or benefits administration.
• Experience with Canadian and US payroll.
• Proficiency with Rippling HRIS and Payroll.
• PCP/CP or similar certification is a plus.
• Experience with US benefits programs (medical, dental, vision, 401(k)).
• Seasonal/shift-based work experience preferred.

Responsibilities

• Process biweekly payroll for Canadian and US staff via Rippling.
• Review timesheets, hours, and pay changes for accuracy.
• Ensure correct wages, overtime, vacation and holiday pay.
• Process and reconcile payroll deductions.
• Generate payroll reports for month-end and year-end.
• Coordinate benefits enrollment and renewals for Canada and US.
• Respond to payroll and benefits inquiries and maintain records.

Skills

Payroll

Benefits

Rippling HRIS

Multi-location payroll

US & Canada payroll

Certification asset

Education

PCP/CP certification (or pursuing)

Tools

Rippling HRIS

Job description

Flyover Attractions in Chicago, IL seeks a part-time payroll and benefits specialist to support our People and Finance teams, handling payroll for US and Canada and benefits administration.

This 20-hour-per-week role offers hybrid work with occasional on-site presence, and collaboration across Canadian and US locations.

You’ll own day-to-day payroll cycles, navigate benefits, and assist with light accounting tasks as needed.