Part-Time Payroll & Benefits Specialist | Hybrid (Chicago)

Flyover Attractions, Inc.; Chicago (IL); Hybrid; USD 32,000 - 36,000; Part time

Job summary

Flyover Attractions, Inc. is seeking a part-time Payroll & Benefits Specialist to support our People and Finance teams with accurate, timely payroll and thoughtful benefits administration. This 20-hour-per-week role can be based in Chicago and collaborates across Canadian and US locations.

You will own day-to-day payroll, guide benefits navigation, and keep records compliant. Some light accounting work like expense processing may be involved in a hybrid setup with occasional onsite work at Navy

Qualifications

• 3 years of hands-on payroll and/or benefits administration experience, ideally in a multi-location or multi-entity environment.
• Direct experience with Canadian and US payroll
• Experience working with Rippling HRIS and Payroll
• PCP/CP or similar payroll certification (or working toward it) is an asset
• Experience with US benefits programs (medical, dental, vision, 401(k), FSA/HSA, etc.)
• Experience in seasonal/shift-based work environments

Responsibilities

• Process Canadian and US payroll biweekly using Rippling, including hires, terminations, and job changes.
• Review timesheets, hours, pay changes, and ensure proper approvals.
• Coordinate benefits enrollment and renewals with carriers and vendors.
• Assist with expense reviews, account reconciliations, and ad hoc reporting.

Skills

Payroll experience

Benefits administration

Cross-location work

Education

Payroll certification (PCP/CP)

Tools

Rippling HRIS

Job description

Flyover Attractions, Inc. is seeking a part-time Payroll & Benefits Specialist to support our People and Finance teams with accurate, timely payroll and thoughtful benefits administration. This 20-hour-per-week role can be based in Chicago and collaborates across Canadian and US locations.

You will own day-to-day payroll, guide benefits navigation, and keep records compliant. Some light accounting work like expense processing may be involved in a hybrid setup with occasional onsite work at Navy