Payroll & Benefits Specialist

About the role

We’re looking for a part‑time Payroll & Benefits Specialist to support our People and Finance teams with accurate, timely payroll and thoughtful benefits administration. This role is 20 hours per week and can be based in Chicago, with regular collaboration across Canadian and US locations.

You’ll own the day‑to‑day payroll cycles, help team members navigate their benefits, and keep our records clean and compliant. There’s also room to support light accounting work like expense processing.

This role offers a hybrid work arrangement with the flexibility to work remotely within Chicago, IL. Occasional onsite presence at our Flyover location on the Navy Pier will be required based on business needs, meetings, or team support.

Compensation: $23-$26

USD/hourly

• Prepare and process biweekly payroll for Canadian and US team members via Rippling, including new hires, terminations, and job changes.
• Review and validate timesheets, hours, and pay changes for accuracy and proper approvals.
• Ensure correct calculation of wages, overtime, vacation, statutory holiday pay, and other earnings.
• Process and reconcile payroll deductions (benefits, retirement plans, garnishments, etc.).
• Generate payroll reports and support for month‑end and year‑end processes (e.g., T4s, ROEs, W‑2 support, and related summaries as applicable).
• Partner with People and Finance teams to resolve payroll discrepancies and answer related questions.

• Coordinate benefits enrollment, changes, and terminations for Canadian and US team members, ensuring accuracy and timely submission to carriers and vendors.
• Maintain up‑to‑date records of eligibility, coverage levels, and dependent information.
• Act as the first point of contact for benefits questions, helping team members understand coverage, claims processes, and policy changes.
• Support annual benefits renewals and open enrollment activities (communications, forms, data audits).
• Reconcile monthly benefits invoices and flag discrepancies.

• Respond promptly and professionally to payroll and benefits inquiries, escalating complex issues when needed.
• Maintain accurate and confidential employee records in HR/payroll systems in line with privacy and employment legislation.
• Support compliance with applicable federal and provincial/state regulations related to payroll and benefits in Canada and the US.
• Help document and improve payroll and benefits procedures.

• Assist with expense report review, coding, and submission into accounting/expense systems.
• Support account reconciliations related to payroll and benefits (e.g., payroll clearing accounts, benefits payable).
• Provide ad hoc reporting and data pulls for People, Finance, and leadership teams.

• 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

At Flyover, we value a strong team built on respect and professionalism. We seek individuals who bring talent, enthusiasm, and a commitment to great guest experiences. Our hiring decisions are based on skills and qualifications, as well as alignment with our mission and values.

We evaluate qualified applicants without regard to race, color, age, religion, gender, sexual orientation, disability, veteran status, and other protected characteristics. To handle this job successfully, any person hired must be able to perform each task effectively. We welcome all applicants and are happy to provide accommodation upon request.