Payroll and People Operations Specialist
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Job Description
Payroll and People Operations Specialist processing accurate multi-state payroll for Progressive Leasing’s fintech lease-to-own businesses. Supporting compliance, tax reporting, employee inquiries, and payroll automation.
Responsibilities:
- Process multi-state payroll accurately and on schedule in Workday, including regular cycles and off-cycle runs
- Reconcile payroll data before each processing cycle and proactively resolve discrepancies
- Monitor stock/equity transaction settlement dates and execute timely tax deposits, including same-day deposits when required
- Audit payroll results for accuracy and compliance
- Execute and validate tax deposits through Workday and ADP SmartCompliance; escalate discrepancies with clear documentation
- Maintain payroll records according to federal, state, and local requirements
- Leverage or learn AI-driven payroll tools, including Workday Payroll Agents, for processing and audit workflows
- Monitor payroll tax thresholds and deadlines, including next-day deposit triggers
- Support year-end activities including 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
- Partner with HR Business Partners and Total Rewards on compensation changes, new hire setup, terminations, and leave processing
- Respond to employee payroll inquiries
- 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
- 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 communication skills, with ability to simplify payroll complexity for non-payroll audiences
- Proficiency in Excel
- Openness to leveraging AI tools to improve workflows
- Experience using AI tools to improve accuracy, efficiency, or process automation
- 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
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
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