Payroll, Benefits, and Leave of Absence Sr. Manager

Remote - US - East Coast/MidWest 

Reports to: SVP, People & Culture

Job Summary

We are seeking an experienced Payroll, Benefits, and Leave of Absence (LOA) Manager with a strong background in payroll and tax system integration to lead and optimize our multi-state payroll, benefits, and leave operations. This role is responsible for managing payroll and LOA vendors, overseeing benefits administration, ensuring compliance with federal and state regulations, and supporting tax registration and reporting across 40+ states.

The ideal candidate is highly organized, detail-oriented, and proficient in platforms such as Paylocity and SuccessFactors, with hands-on experience in multi-state tax registration, leave management, and employee benefits programs. This role plays a critical role in ensuring seamless operations, regulatory compliance, and a positive employee experience.

Payroll Management

• Managing and directing multi-state, bi-weekly payroll operations for both salaried and hourly employees, ensuring accuracy, timeliness, and regulatory compliance in partnership with a managed service provider
• Maintaining and ensuring accuracy of federal, state, and local payroll laws, including wage and hour regulations, tax withholding, and reporting requirements
• Overseeing the setup and maintenance of employee records, earnings, deductions, direct deposits, and tax configurations within the payroll system
• Conducting regular payroll audits and reconciliations to identify discrepancies, ensure data integrity, and support internal and external audit requirements
• Managing quarterly and year-end payroll activities, including W-2 processing, tax filings, and coordination with third-party vendors
• Collaborating closely with Finance to align payroll data with general ledger reporting and accruals
• Partnering with HR and Benefits teams to ensure accurate processing of benefits deductions, bonuses, commissions, and leave-related pay
• Maintaining tax setup and configurations in payroll systems to ensure proper jurisdictional reporting
• Responding to tax notices and inquiries from government agencies, resolving discrepancies and maintaining documentation
• Continuously evaluate and improve payroll processes, leveraging automation and system capabilities to enhance efficiency and reduce risk

Benefit Management

• Overseeing the administration of comprehensive employee benefits programs, including but not limited to:
  • Medical, dental, and vision insurance
  • Health Savings Accounts (HSA) and Flexible Spending Accounts (FSA)
  • Life and AD&D insurance
  • Short- and long-term disability
  • Employee Assistance Programs (EAP)
  • Wellness initiatives and voluntary benefits
  • Workers’ Compensation
• Leading the annual benefits renewal and open enrollment process, including plan design evaluation, cost analysis, employee communications, and system configuration
• Serving as the primary liaison with benefits brokers, carriers, and third-party administrators to ensure service quality, resolve escalated issues, and negotiate plan renewals
• Monitoring and ensure compliance with all applicable federal and state regulations, including ACA, COBRA, HIPAA, ERISA, and Section 125
• Maintaining accurate benefits data in HRIS/payroll systems and ensure seamless integration with payroll processing
• Conducting regular audits of benefits enrollment, deductions, and carrier invoices to ensure accuracy and cost control
• Developing and deliver employee education materials and training sessions to promote understanding and utilization of benefits offerings
• Supporting system integration efforts by aligning and harmonizing benefits offerings, managing data migration, and ensuring compliance during transitions

Leave of Absence (LOA) Management

• Managing LOA vendor
• Administering Short-Term and Long-Term Disability (STC/LTD) processes in partnership with Unum
• Administering and tracking all types of employee leaves (FMLA, ADA, parental, military, etc.).
• Ensuring compliance with federal and state leave laws
• Tracking LOA-related premium payments
• Managing wage replacement process upon return for paternity leave
• Liaising with the legal and the people team on compliance and employee leave matters
• Serving as a liaison between employees, managers, and third-party administrators

Payroll System Integration with Tax Compliance

• Leading the integration of payroll systems with a strong focus on automated tax compliance, ensuring accurate configuration of federal, state, and local tax jurisdictions
• Collaborating with HRIS, IT, and payroll vendors to implement real-time tax calculations, including multi-state withholding, unemployment insurance, and local tax codes
• Ensuring proper setup of tax location mapping, employee work and residence tax profiles, and reciprocal agreements within the payroll system
• Validating and testing system-generated tax forms (e.g., W-2, 941, 940, state equivalents) for accuracy and compliance prior to filing deadlines
• Monitoring and maintaining system updates related to tax rate changes, wage base limits, and legislative updates, ensuring timely implementation
• Supporting integration of third-party tax filing services, ensuring seamless data exchange and reconciliation between systems

Experience, Skills, and Qualifications

• Minimum of 5-7 years of experience in payroll, benefits, and/or leave of absence administration.
• Strong knowledge of federal, state, and local laws and regulations related to payroll, benefits, and leave
• Systems Knowledge: Paylocity, HRIS, SuccessFactors, benefit platforms including 401(k)
• Regulatory Compliance: Strong understanding of payroll tax law, benefits compliance, and reporting requirements (ACA, EEO, Pay Equity, PFML and 401(k)
• Analytical and Calculation Skills: Ability to manage audits, track compliance deadlines, and resolve payroll/benefits discrepancies utilizing strong analytical and calculation skills
• Communication & Collaboration: Strong ability to liaise and effectively communicate with employees, people team, legal staff, vendors and internal stakeholders
• Ability to manage multiple priorities and meet deadlines
• Ability to work independently and as part of a team
• Experience with vendor management
• Experience with process improvement and project management. 
• This is a 100% remote position.
• Occasional, pre-scheduled travel may be required once or twice per year.
• Preferred candidates would be located in the Eastern or Central time zones; however, exceptional candidates in Mountain or Pacific time zones will also be considered

Travel Requirements

• Domestic and international travel as needed (approximately 10%)