Payroll and People Operations Analyst; Remote

Overview

PROG Holdings is a Fin Tech holding company that includes Progressive Leasing, Purchasing Power, and Four. Progressive Leasing is the lead provider of in‑store and e‑commerce lease‑to‑own solutions. The company is seeking a Payroll and People Operations Analyst to support payroll operations across the PROG Holdings family of companies.

• Payroll Processing & Execution
  • Process multi‑state payroll accurately and on schedule in Workday, including regular cycles and off‑cycle runs.
  • Reconcile payroll data prior to each processing cycle and proactively resolve discrepancies.
  • Monitor stock/equity transaction settlement dates and ensure timely tax deposit execution, including same‑day when required.
  • Audit payroll results to ensure accuracy and compliance.
  • Execute and validate tax deposits through Workday and ADP Smart Compliance; document and resolve discrepancies.
  • Maintain payroll records in accordance with federal, state, and local requirements.
  • Leverage AI‑driven payroll tools, including Workday Payroll Agents, to support processing and audit workflows.
• Compliance & Reporting
  • Monitor payroll tax thresholds and deadlines, including next‑day deposit triggers.
  • Support year‑end activities such as W‑2 processing, ACA reporting, and payroll tax reconciliation.
  • Assist with audits and regulatory inquiries by preparing accurate payroll documentation.
  • Track and document key payroll timelines to support accountability and continuous improvement.
• People Operations Support
  • Partner with HR Business Partners and Total Rewards on compensation changes, new hire setup, terminations, and leave processing.
  • Respond to employee payroll inquiries with clarity and professionalism.
  • Help document and standardize processes to reduce single points of failure.
  • Contribute to Workday enhancements and broader People Operations process improvements.

• 3–5 years of hands‑on payroll processing experience, ideally in a multi‑state environment.
• Hands‑on experience with Workday Payroll (required); experience with equity or stock‑based payroll is a strong plus.
• Working knowledge of ADP Smart Compliance 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.
• Clear, professional communicator who can simplify payroll complexity for non‑payroll audiences.
• Proficiency in Excel and openness to leveraging AI tools to improve workflows.
• Experience using AI tools to improve accuracy, efficiency, or process automation.
• Curiosity and adaptability as roles and processes continue to evolve.
• CPP (Certified Payroll Professional) is a plus, not required.

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

Progressive Leasing welcomes and encourages diversity in the workplace. We do not discriminate in any aspect of employment on the basis of race, color, religion, national origin, ancestry, gender, sexual orientation, gender identity and/or expression, age, veteran status, disability, or any other characteristic protected by federal, state, or local employment discrimination laws where Progressive Leasing does business.