Senior Payroll Specialist

HealthDrive•Framingham, MA

10d•$85,000•Hybrid

About The Position

HealthDrive is seeking an experienced Senior Payroll Specialist to join their payroll team and drive strategic initiatives across their multi-entity, multi-state organization. This senior-level position requires deep expertise in complex payroll operations, tax compliance, and team leadership to ensure accurate, timely, and compliant payroll processing for their diverse workforce. The role is hybrid, with in-office days in the HealthDrive Framingham, MA office. The compensation offered is $85,000.

Requirements

5-7 years of progressive payroll experience
Extensive experience with multi-entity, multi-state payroll operations
Proven track record managing complex payroll calculations and scenarios
Strong background in federal, state, and local payroll tax compliance
Expert knowledge of payroll systems (Preferably UKG)
Advanced proficiency in Excel and payroll reporting tools
Experience with HRIS integrations and data management
Knowledge of wage and hour laws, FLSA, and employment regulations
Strong analytical and problem-solving capabilities
High attention to detail and accuracy
Ability to work under pressure and meet tight deadlines

Nice To Haves

Bachelor's degree in Accounting, Accounting/Finance, or related field
Professional certifications (CPP or FPC, preferred)
Experience implementing new payroll systems or processes

Responsibilities

End-to-end payroll processing for multiple entities across various states and localities
Ensure accurate calculation of complex payroll elements including bonuses, overtime, and performance-based compensation
Lead multi-state and local payroll tax compliance initiatives
Reconcile quarterly and annual payroll tax filings
Manage relationships with tax authorities and respond to audits or inquiries
Stay current on changing federal, state, and local tax regulations
Ensure compliance with wage and hour laws across all jurisdictions
Manage payroll systems (UKG), integrations, and vendor relationships
Develop and maintain standard operating procedures and internal controls
Drive process improvements and automation initiatives to enhance efficiency and accuracy
Complete end to end payroll ownership for all M&A
Collaborate with senior leadership on payroll-related strategic decisions and budget planning
Build, lead, and develop a high-performing payroll team
Foster a culture of continuous improvement and excellence
Manage team performance and conduct regular reviews