People Operations / Payroll Specialist

SpotHero•Chicago, IL

1d•Hybrid

About The Position

The People Operations Specialist plays a key role in delivering a seamless, compliant, and high-quality employee experience across SpotHero’s US and Canadian workforce. This role owns the execution of payroll, benefits, leave, and core employee lifecycle operations, while partnering closely with People Leadership to ensure accuracy, compliance, and continuous improvement. With a strong focus on systems, data, and process optimization, this individual helps scale People Operations and enhance how we support employees across the organization.

Requirements

3+ years of experience in People Operations, HR, or a related field in mid-sized SaaS, Technology, Marketing or similar industries
Direct experience processing multi-state, multi-country payroll (U.S. required; Canada strongly preferred and payroll certification a plus)
Experience administering benefits and managing leave of absence processes in conjunction with additional people programs (i.e. wellness, recognition)
Knowledge of U.S. payroll regulations and familiarity with multi-country requirements (Canada preferred)
Working knowledge of U.S. employment laws (federal and state) and exposure to employment regulations outside the US (Canada preferred)
Experience with Payroll, HR, and Benefits systems (ADP WorkforceNow and TeamPay strongly preferred)
Strong analytical skills and comfort working with data (Excel/Google Sheets required)
High attention to detail and a commitment to accuracy
Reliability with using sound judgement in handling sensitive and confidential information
Ability to communicate effectively in a clear, professional, and approachable way
Ability to manage multiple priorities in a fast-paced environment
Must be legally authorized to work in the US and not require sponsorship for employment now or in the future.

Nice To Haves

Payroll certification a plus
Canada payroll strongly preferred
Exposure to employment regulations outside the US (Canada preferred)

Responsibilities

Own end-to-end payroll processing for U.S. and Canadian employees, ensuring accuracy, timeliness, and compliance across all pay cycles
Process payroll changes, including new hires, terminations, compensation updates, bonuses, and deductions
Partner with People Leadership to reconcile payroll each cycle, validate outputs, and ensure accuracy prior to finalization
Audit payroll data, investigate discrepancies, and proactively resolve issues
Identify trends or recurring issues across payroll cycles and recommend process improvements to enhance accuracy and efficiency
Ensure compliance with U.S. federal/state and Canadian federal/provincial payroll regulations
Support payroll reporting, accruals, and audit readiness
Administer employee benefits programs (health, retirement, wellness) across the U.S. and Canada, ensuring accurate enrollment, employee support, deductions, audits, and reporting
Manage leave of absence programs in compliance with federal, state, and provincial regulations, partnering with employees and managers throughout the process
Support and execute open enrollment, including employee communications, vendor coordination, and system updates
Review and validate benefit invoices and ensure alignment with payroll and vendor data
Develop and enhance wellness initiatives that support employee well-being
Identify opportunities to improve benefits and leave processes, ensuring compliance while elevating the employee experience
Manage and optimize the People Team service desk, delivering a high-quality, responsive support and track and report on metrics to ensure a five-star employee experience
Own onboarding and offboarding processes, ensuring a seamless, consistent, and heroic employee experience across the lifecycle
Maintain the org charts and ensure accurate employee data for integrity across HR systems
Ensure People Operations practices comply with U.S. federal and state employment laws and Canadian federal and provincial regulations, including proper documentation and recordkeeping
Partner with Legal, Finance, and People Leadership to support compliance initiatives, audits, and policy adherence
Serve as a trusted resource for employees and managers, providing timely, thoughtful support
Build and maintain people and payroll reports (headcount, turnover, compensation, etc.)
Translate data into insights to support People Team and business decisions
Develop expertise in HRIS and payroll systems; support ongoing optimization and enhancements
Identify inefficiencies and implement scalable, compliant process improvements across People Operations
Document and maintain clear SOPs to ensure consistency and operational excellence
Partner cross-functionally with Finance, IT, and Legal to streamline workflows and improve systems