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.

Employee Value Proposition (EVP): PROG is dedicated to providing people with opportunity; opportunity for inclusive collaboration, opportunity for innovation, and opportunity for development.

WE ARE: A team focused on delivering payroll with accuracy, efficiency, and care. Progressive Leasing is known for the high-quality support we provide, and we’re always looking for ways to improve how we work and serve our people. We value a culture of belonging, inclusion, and collaboration, and we respect the unique contributions each person brings.

YOU ARE: Someone who enjoys working in a highly collaborative environment and partnering closely with our Payroll Manager. You’re comfortable owning the details and execution of payroll, and you understand how critical this work is to the overall employee experience. You take pride in accuracy, stay on top of deadlines, and bring a strong sense of accountability to everything you do. You’re someone who looks for ways to simplify and automate work, and you’re open to using AI and new tools to help improve accuracy, speed, and scalability.

YOUR DAY-TO-DAY:

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
Help document and standardize processes to reduce single points of failure
Contribute to Workday enhancements and broader People Operations process improvements

YOU’LL BRING:

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 — 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 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 our organization — from payroll validation to workflow automation — and that will continue to grow. We’re looking for someone who is curious, adaptable, and interested in using technology to improve how work gets done.

WE OFFER:

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

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.

Progressive Leasing

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Payroll and People Operations Analyst (Remote)