Payroll and People Operations Analyst (Remote)

Payroll and People Operations Analyst

PROG Holdings is seeking a Payroll and People Operations Analyst to support payroll operations across the PROG Holdings family of companies, including Progressive Leasing, Purchasing Power, Four, and Money App. The ideal candidate will have 3–5 years of hands-on payroll processing experience, ideally in a multi-state environment, and proficiency in Workday Payroll and ADP SmartCompliance.

• Multi-state payroll processing in Workday, including regular cycles and off-cycle runs
• Reconciliation of payroll data prior to each processing cycle and proactive resolution of discrepancies
• Monitoring stock/equity transaction settlement dates and ensuring timely tax deposit execution, including same-day deposits when required
• Auditing payroll results to ensure accuracy and compliance
• Executing and validating tax deposits through Workday and ADP SmartCompliance; escalating discrepancies with clear documentation
• Maintaining payroll records in accordance with federal, state, and local requirements
• Leveraging AI-driven payroll tools, including Workday Payroll Agents, to support processing and audit workflows

Compliance & Reporting

• Monitoring payroll tax thresholds and deadlines, including next-day deposit triggers
• Supporting year-end activities such as W-2 processing, ACA reporting, and payroll tax reconciliation
• Aiding in audits and regulatory inquiries by preparing accurate payroll documentation
• Tracking and documenting key payroll timelines to support accountability and continuous improvement

People Operations Support

• Partnering with HR Business Partners and Total Rewards on compensation changes, new hire setup, terminations, and leave processing
• Responding to employee payroll inquiries with clarity and professionalism
• Documenting and standardizing processes to reduce single points of failure
• Contributing to Workday enhancements and broader People Operations process improvements

Skills & Experience

• Hands-on experience with Workday Payroll (required)
• Experience with equity or stock-based payroll is a strong plus
• Working knowledge of ADP SmartCompliance and federal, state, and local payroll tax requirements, including IRS deposit rules and Form 941 reconciliation
• Demonstrated ability to manage tight, non-negotiable deadlines with a high degree of accuracy
• Strong reconciliation and analytical skills
• Comfort operating in a fast-paced environment where processes are still being built and improved
• Clear, professional communicator who can simplify payroll complexity for non-payroll audiences
• Proficiency in Excel
• Openness to leveraging AI tools to improve workflows
• Experience using AI tools to improve accuracy, efficiency, or process automation (payroll or adjacent workflows)
• Comfort experimenting with automation, prompts, and system capabilities to reduce manual work
• Curiosity and adaptability as roles and processes continue to evolve

Benefits

• Competitive compensation + bonus potential
• Full health benefits; medical, dental, vision, and life insurance + paid parental leave
• Company-matched 401(k)
• Paid time off + holidays + volunteer time
• Employee resource groups
• Employee stock purchase program
• Tuition reimbursement
• Charitable gift matching
• Job-required equipment and services provided