Payroll and People Operations Specialist (Remote)

Prog Leasing, LLC; Northern (KY); Hybrid; USD 70,000 - 90,000; Full time

Benefits offered by this job

Bonus potential

Health benefits

401(k)

PTO & holidays

Employee resource groups

Employee stock purchase

Tuition reimbursement

Charitable gift matching

Equipment provided

Job summary

Progressive Leasing seeks a Payroll & People Operations Specialist to manage multi-state payroll in Workday, ensure accuracy and compliance, and support year-end tasks. The role emphasizes collaboration with Payroll Manager, leveraging AI tools, and improving processes to scale our growing workforce.

You will handle tax deposits, audits, and regulatory inquiries while maintaining payroll records and partnering with Total Rewards on changes and new hires. Remote-friendly within the United States.

Qualifications

• 3–5 years of hands-on payroll processing experience, ideally in a multi-state environment.
• Hands-on experience with Workday Payroll (required); equity or stock-based payroll a plus.
• Working knowledge of ADP SmartCompliance and federal/state/local payroll tax requirements.

Responsibilities

• Process multi-state payroll accurately and on schedule in Workday.
• Reconcile payroll data and resolve discrepancies.
• Monitor tax deposits and ensure timely deposits; audit payroll for accuracy and compliance.
• Support year-end activities like W-2 and ACA reporting.
• Assist with audits and regulatory inquiries with accurate payroll documentation.

Skills

Payroll processing

Attention to detail

Analytical thinking

Deadline management

Clear communication

Adaptability

Tools

Workday Payroll

ADP SmartCompliance

Excel

AI tools

Workday Agents

Job description

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 Specialist 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; elevate 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 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.