Payroll and People Operations Analyst (Remote)

Payroll And People Operations AnalystProgressive 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, a FinTech holding company with three business segments: Progressive Leasing, Purchasing Power, and Four.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 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 & ExecutionProcess multi-state payroll accurately and on schedule in Workday, including regular cycles and off-cycle runsReconcile payroll data prior to each processing cycle and proactively resolve discrepanciesMonitor stock/equity transaction settlement dates and ensure timely tax deposit execution, including same-day when requiredAudit payroll results to ensure accuracy and complianceExecute and validate tax deposits through Workday and ADP SmartCompliance; escalate discrepancies with clear documentationMaintain payroll records in accordance with federal, state, and local requirementsLeverage (or learn) AI-driven payroll tools, including Workday Payroll Agents, to support processing and audit workflowsCompliance & ReportingMonitor payroll tax thresholds and deadlines, including next-day deposit triggersSupport year-end activities such as W-2 processing, ACA reporting, and payroll tax reconciliationAssist with audits and regulatory inquiries by preparing accurate payroll documentationTrack and document key payroll timelines to support accountability and continuous improvementPeople Operations SupportPartner with HR Business Partners and Total Rewards on compensation changes, new hire setup, terminations, and leave processingRespond to employee payroll inquiries with clarity and professionalismHelp document and standardize processes to reduce single points of failureContribute to Workday enhancements and broader People Operations process improvementsYou'll bring:3–5 years of hands-on payroll processing experience, ideally in a multi-state environmentHands-on experience with Workday Payroll (required); experience with equity or stock-based payroll is a strong plusWorking knowledge of ADP SmartCompliance and federal, state, and local payroll tax requirements, including IRS deposit rules and Form 941 reconciliationDemonstrated ability to manage tight, non-negotiable deadlines with a high degree of accuracyStrong reconciliation and analytical skills — you catch issues before they become problemsComfort operating in a fast-paced environment where processes are still being built and improvedClear, professional communicator who can simplify payroll complexity for non-payroll audiencesProficiency in Excel and openness to leveraging AI tools to improve workflowsExperience 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 workCuriosity and adaptability as roles and processes continue to evolveCPP (Certified Payroll Professional) is a plus, not requiredAI-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 potentialFull health benefits; medical, dental, vision, and life insurance + paid parental leaveCompany-matched 401(k)Paid time off + holidays + volunteer timeEmployee resource groupsEmployee stock purchase programTuition reimbursementCharitable gift matchingJob-required equipment and services providedProgressive 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.