Payroll and People Operations Analyst (Remote)

Progressive Leasing • Remote - UT, UT

3d • Remote

About The Position

Progressive Leasing is a leading provider of in-store and e-commerce lease-to-own solutions. With more than 20 years in FinTech, we’ve grown from start-up to industry leader by innovating, simplifying, and valuing people. We are a subsidiary of PROG Holdings (NYSE: PRG), a FinTech holding company with three business segments: Progressive Leasing, Purchasing Power (a leading employee purchase program for consumer products and services using payroll deduction), and Four, a Buy Now Pay Later (BNPL) platform. PROG is looking for a Payroll and People Operations Analyst to join our People Operations team. This role supports payroll operations across the PROG Holdings family of companies — including Progressive Leasing, Purchasing Power, Four, and Money App — and helps ensure accurate, timely, and compliant payroll processing for a dynamic and 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.

Requirements

• 3–5 years of hands-on payroll processing experience, ideally in a multi-state environment
• Hands-on experience with Workday Payroll (required)
• 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 — you catch issues before they become problems
• 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
• Comfort experimenting with automation, prompts, and system capabilities to reduce manual work
• Curiosity and adaptability as roles and processes continue to evolve

Nice To Haves

• Experience with equity or stock-based payroll is a strong plus
• Experience using AI tools to improve accuracy, efficiency, or process automation (payroll or adjacent workflows)
• CPP (Certified Payroll Professional) is a plus, not required

Responsibilities

• 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
• 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
• 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

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

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed