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People Operations / Payroll Specialist

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SpotHero

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Location:
United States , Chicago

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Category:
Human Resources

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Contract Type:
Employment contract

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Salary:

65920.00 - 90000.00 USD / Year
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Job Description:

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.

Job Responsibility:

  • Own end-to-end payroll processing for U.S. and Canadian employees
  • Process payroll changes including new hires, terminations, compensation updates, bonuses, and deductions
  • Partner with People Leadership to reconcile payroll each cycle
  • Audit payroll data, investigate discrepancies, and proactively resolve issues
  • Identify trends or recurring issues across payroll cycles and recommend process improvements
  • Ensure compliance with U.S. federal/state and Canadian federal/provincial payroll regulations
  • Support payroll reporting, accruals, and audit readiness
  • Administer employee benefits programs across U.S. and Canada
  • Manage leave of absence programs in compliance with regulations
  • Support and execute open enrollment
  • Review and validate benefit invoices
  • Develop and enhance wellness initiatives
  • Manage and optimize the People Team service desk
  • Own onboarding and offboarding processes
  • Maintain org charts and ensure accurate employee data
  • Ensure People Operations practices comply with employment laws
  • Partner with Legal, Finance, and People Leadership on compliance
  • Serve as a trusted resource for employees and managers
  • Build and maintain people and payroll reports
  • Translate data into insights
  • Develop expertise in HRIS and payroll systems
  • Identify inefficiencies and implement scalable process improvements
  • Document and maintain SOPs
  • Partner cross-functionally with Finance, IT, and Legal

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
  • Seeking Candidates in: Chicago, IL - 1 day per week in office

Nice to have:

  • Canada payroll experience
  • Payroll certification
  • Canada multi-country requirements
  • Exposure to employment regulations outside US (Canada preferred)
  • TeamPay experience
What we offer:
  • Generous portion of Medical Premiums covered
  • 50% of Dental and Vision Premiums covered
  • Company-sponsored Life Insurance, STD, and AD&D coverage
  • 401(k) with match and immediate vesting
  • Comprehensive leave policies
  • Flexible PTO policy
  • Grubhub weekly lunch stipend for in-office days
  • Udemy License and Personal Learning Budget
  • Annual parking stipend
  • Employee Resource Groups
  • Wellness program
  • Recognition awards

Additional Information:

Job Posted:
May 15, 2026

Employment Type:
Fulltime
Work Type:
Hybrid work
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