Senior Payroll Specialist

About HealthDrive:

HealthDrive delivers on-site dentistry, optometry, podiatry, audiology, behavioral health, and primary care services to residents in long-term care, skilled nursing, and assisted living facilities. Each specialty offered by HealthDrive is one that directly impacts the quality of daily life for the deserving residents we serve. HealthDrive connects patients in need of vital healthcare to doctors committed to dignity and excellence.

About the Role:

We are seeking an experienced Senior Payroll Specialist to join our payroll function and drive strategic initiatives across our 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 our diverse workforce.

Location:

This role is hybrid with in-office days in the HealthDrive Framingham, MA office.

Compensation: $85,000

Key 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
• Stay current on changing federal, state, and local tax regulations
• Ensure compliance with wage and hour laws across all jurisdictions
• Build, lead, and develop a high-performing payroll team
• Foster a culture of continuous improvement and excellence
• Manage team performance and conduct regular reviews

Required Qualifications:

• Experience:
  • 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

• Technical Skills:

  • 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

Preferred Qualifications:

• • Bachelor's degree in Accounting, Accounting/Finance, or related field

  • Professional certifications (CPP or FPC, preferred)

  • Experience implementing new payroll systems or processes

What We Offer:

• Competitive salary commensurate with experience

• Comprehensive benefits package including health, dental, and vision insurance

• 401(k) with company matching

• Professional development opportunities

• Flexible work arrangements 

• Opportunity to make a significant impact in a growing organization