Senior Tax Payroll Specialist

Stride, Inc.

7d • $23 - $40 • Remote

About The Position

Senior Payroll Tax Specialist (50% Payroll Tax Ownership/ 50% Payroll Operations) What you’ll do: Payroll Tax Ownership (50%) Primary Focus Serve as the subject-matter expert for all federal, state, and local payroll tax matters. Independently manage all tax notices, amendments, agency correspondence, and escalations. Own state and local tax registrations, including complex jurisdictions such as PA, OH, and KY LST. Assess tax implications for address change, reciprocity, multi-state moves, and remote work scenarios. Ensure accurate taxation of equity, ESPP, fringe benefits, imputed income, and other complex earnings. Perform prior-quarter and prior-year tax adjustments in Workday and coordinate amendments with OSV. Support quarterly and year-end audits, including W-2 accuracy, income reporting, and reconciliation. Provide tax training to the payroll team and serve as a tax escalation point and backup to the Payroll Director. Stay current on tax legislation and ensure Workday configuration remains compliant. Payroll Operations (50%) Process biweekly, multi-state exempt payroll ended in Workday and OSV with minimal errors. Reconcile payroll results period-over-period and resolve discrepancies proactively. Calculate prorated wages and deductions for hires, terminations, and job/status changes. Ensure accurate withholding of taxes and payroll deductions, strong understanding of reciprocity rules. Demonstrate deep knowledge of Workday retros and associated processing requirements. Perform Workday administrative tasks, including integration testing for Payroll, Time Tracking, and Absence. Maintain payroll records in compliance with SOX, federal, state, and local regulations. Troubleshoot and resolve all payroll issues-including tax-related items-with limited supervision. Provide excellent customer service through the ticketing system and partner with HR and Finance as needed.

Requirements

• 7+ years of progressive payroll administration experience, with Workday as the primary and most recent system.
• 7+ years of experience independently handling payroll tax notices, amendments, and multi-state registrations.
• Strong experience with PA, OH, KY LST and other complex local tax jurisdictions.
• A minimum of 3 years of experience supporting finance and accounting with month end closing and reconciliation.
• Experience in ticketing systems (i.e., Fresh Service, Zendesk).
• Ability to prioritize (and re-prioritize) in a fast-paced environment.
• Experience leading meetings and providing backup support to the Payroll Director.

Nice To Haves

• Bachelor’s degree or equivalent additional experience strongly preferred.
• Strong interpersonal skills, ability to interact with all levels of the organization and provide strong customer service.
• Excellent problem solving/judgment skills with a high level of attention to detail.
• Superior written and oral communication skills.
• Strong commitment to the development and knowledge sharing.
• Proficiency in Microsoft Excel and other Office applications.
• Ability to work Eastern Time Zone hours and occasional overtime during payroll cycles.
• CPP/FPC Certification preferred

Responsibilities

• Serve as the subject-matter expert for all federal, state, and local payroll tax matters.
• Independently manage all tax notices, amendments, agency correspondence, and escalations.
• Own state and local tax registrations, including complex jurisdictions such as PA, OH, and KY LST.
• Assess tax implications for address change, reciprocity, multi-state moves, and remote work scenarios.
• Ensure accurate taxation of equity, ESPP, fringe benefits, imputed income, and other complex earnings.
• Perform prior-quarter and prior-year tax adjustments in Workday and coordinate amendments with OSV.
• Support quarterly and year-end audits, including W-2 accuracy, income reporting, and reconciliation.
• Provide tax training to the payroll team and serve as a tax escalation point and backup to the Payroll Director.
• Stay current on tax legislation and ensure Workday configuration remains compliant.
• Process biweekly, multi-state exempt payroll ended in Workday and OSV with minimal errors.
• Reconcile payroll results period-over-period and resolve discrepancies proactively.
• Calculate prorated wages and deductions for hires, terminations, and job/status changes.
• Ensure accurate withholding of taxes and payroll deductions, strong understanding of reciprocity rules.
• Demonstrate deep knowledge of Workday retros and associated processing requirements.
• Perform Workday administrative tasks, including integration testing for Payroll, Time Tracking, and Absence.
• Maintain payroll records in compliance with SOX, federal, state, and local regulations.
• Troubleshoot and resolve all payroll issues-including tax-related items-with limited supervision.
• Provide excellent customer service through the ticketing system and partner with HR and Finance as needed.

Benefits

• Eligible employees may receive a bonus.
• Stride offers a robust benefits package for eligible employees that can include health benefits, retirement contributions, and paid time off.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Number of Employees: 1,001-5,000 employees