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-$26USD/hourly

What you'll do

Payroll Administration (Canada & US)

oPrepare and processbiweekly payroll for Canadian and US team members via Rippling, including new hires, terminations, and job changes.

oReview and validate timesheets, hours, and pay changes for accuracy and proper approvals.

oEnsure correct calculation of wages, overtime, vacation, statutory holiday pay, and other earnings.

oProcess and reconcile payroll deductions (benefits, retirement plans, garnishments, etc.).

oGenerate payroll reports and support for month‑end and year‑end processes (e.g., T4s, ROEs, W‑2 support, and related summaries as applicable).

oPartner with People and Finance teams to resolve payroll discrepancies and answer related questions.

Benefits Administration

oCoordinate benefits enrollment, changes, and terminations for Canadian and US team members, ensuring accuracy and timely submission to carriers and vendors.

oMaintain up‑to‑date records of eligibility, coverage levels, and dependent information.

oAct as the first point of contact for benefits questions, helping team members understand coverage, claims processes, and policy changes.

oSupport annual benefits renewals and open enrollment activities (communications, forms, data audits).

oReconcile monthly benefits invoices and flag discrepancies.

Employee Support & Compliance

oRespond promptly and professionally to payroll and benefits inquiries, escalating complex issues when needed.

oMaintain accurate and confidential employee records in HR/payroll systems in line with privacy and employment legislation.

oSupport compliance with applicable federal and provincial/state regulations related to payroll and benefits in Canada and the US.

oHelp document and improve payroll and benefits procedures.

Accounting & Administrative Support

oAssist with expense report review, coding, and submission into accounting/expense systems.

oSupport 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.

Qualifications

o3+ years of hands‑on payroll and/or benefits administration experience, ideally in a multi‑location or multi‑entity environment

oDirect experience with Canadian and US payroll

oExperience working with Rippling HRIS and Payroll

oPCP/CP or similar payroll certification (or working toward it) is an asset

oExperience with US benefits programs (medical, dental, vision, 401(k), FSA/HSA, etc.)

oExperience 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.

Thank you for your interest in this opportunity. To ensure a smooth process, we kindly request that candidates refrain from calling about the status of their application. Only those selected for an interview will be contacted. We appreciate your understanding.