Payroll and People Operations Specialist (Remote)

Overview

The organization is seeking a Payroll and People Operations Specialist to join its People Operations team. This role supports payroll operations across the PROG Holdings family of companies, including Progressive Leasing, Purchasing Power, Four, and Money App, ensuring payroll is accurate, timely, and compliant for a growing workforce.

This position can be performed remotely within the United States, with a preference for candidates who can work Mountain or Central time zones.

Responsibilities

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 SmartCompliance; escalate discrepancies with clear documentation
• Maintain payroll records in accordance with federal, state, and local requirements
• Leverage (or learn) 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
• Document and standardize processes to reduce single points of failure
• Contribute to Workday enhancements and broader People Operations process improvements

Requirements

• 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 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 and 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
• CPP (Certified Payroll Professional) is a plus, not required
• AI-enabled tools are already part of how work gets done across the organization and will continue to grow

Preferred Qualifications

• Experience with equity or stock-based payroll

Compensation & 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

Location

Remote within the United States, with a preference for candidates who can work Mountain or Central time zones.