Payroll Specialist

About the role

Hagerty is a company built by drivers for drivers. We put our members at the center of everything we do and are dedicated to making it easier and more enjoyable for enthusiasts to drive and celebrate the machines they love. The Payroll Specialist serves as the subject matter expert for U.S. and international payroll operations, Workday payroll configurations, and payroll controls. Partnering closely with HR, Finance, and Systems teams to ensure accurate and compliant payroll processing, deliver exceptional employee support, and drive continuous process improvement.

Responsibilities

• Payroll Operations
  • Perform key activities necessary in processing payrolls with a high degree of accuracy and adherence to established controls and deadlines.
  • Coordinate with payroll team members using standard operating procedures, documented workflows, and quality checkpoints.
  • Administer imports of external pay files (e.g., benefits, deductions, incentive programs) and payroll inputs including EIBs; validate all transactions for accuracy and compliance.
  • Review and audit payroll inputs for employee data changes including but not limited to new hires, terminations, leaves of absence, compensation changes, shift differentials, retro calculations, and off-cycle payments.
  • Run audit reports, investigate anomalies, and prepare preliminary payroll reconciliations prior to finalizing payroll.
  • Audit payroll output to identify and resolve discrepancies within established payroll timelines.
  • Analyze root causes of manual payroll adjustments or checks and implement corrective actions to reduce recurring issues.
  • Ensure payroll processing complies with all federal, state/provincial regulations, company policies, and internal controls.
  • Perform post-production audits and data maintenance to prepare for upcoming payroll cycles.
• Systems & Process Optimization
  • Complete user testing for system upgrades in partnership with HR Systems teams.
  • Identify and recommend opportunities for process optimization, automation, and improved control design to mitigate potential compliance risks.
  • Develop and maintain detailed payroll SOPs, process documentation, workflows, and reference materials to support standardization and scalability.
  • Create and maintain recurring payroll audit reports and dashboards to support data integrity, trend analysis, and compliance monitoring.
• Employee Support & Cross-Functional Partnership
  • Act as a primary subject matter resource for payroll inquiries from employees, HR business partners, and managers, ensuring timely and accurate issue resolution.
  • Collaborate with HR on complex pay scenarios including pay corrections, retro pay, leaves of absence, FMLA, and other special circumstances.
  • Partner with Finance to align payroll activities with accounting requirements, reconciliations, and reporting needs.
  • Partner with third-party vendors to maintain close communication regarding international payroll matters and collaborate on troubleshooting and resolving payroll issues in a timely and effective manner.
  • Support knowledge-sharing and training within the payroll team to build depth of expertise.
• Compliance, Controls & Reporting
  • Ensure payroll processes comply with federal and state/provincial tax laws, wage and hour regulations, and internal policy standards.
  • Maintain accurate payroll records and reporting to support quarterly and year-end tax filings, audits, and financial reporting.
  • Support internal and external audits by providing documentation, responding to inquiries, and demonstrating process controls.
  • Monitor state-specific payout rules including final pay requirements and PTO payout compliance.

Requirements

• Extensive knowledge of the payroll function including preparation, balancing, internal control, and payroll taxes.
• Strong analytical and problem-solving skills.
• Proficient with Microsoft Office Suite or related software, especially Excel.
• Proficient with HRIS and payroll software, preferably Workday and ADP solutions.
• Ability to work with minimal supervision.
• Demonstrated ability to maintain a high level of confidentiality with data and sensitive materials.
• Ability to be flexible in a fast-paced environment.
• Knowledge of multi-state payroll laws.
• Excellent knowledge in implementation, custom reporting, and production problem resolution for Payroll.
• Ability to handle multiple tasks, prioritize and meet deadlines.
• Strong attention to detail and organization ability.
• Solid verbal and written communication skills.
• Ability to work in a cross-functional team.
• Familiarity with public company requirements, including Sarbanes Oxley and key regulations, if applicable.

Schedule

This position is open to U.S. remote work. However, team members who reside within 20 miles of the Traverse City headquarters will follow a hybrid schedule, working from the office three days per week.