Payroll Director | 10,000+ Employee Workforce

Director of Payroll
Boston, MA (Hybrid)
$170,000-$190,000 + Bonus + Relocation Assistance

Highlights of the Director of Payroll Opportunity:

• 
  
• Join a large, nationally recognized transportation organization operating complex payroll processes across a highly unionized workforce of more than 10,000 employees.
• 
  
• Lead a critical function during a period of significant organizational growth, with planned expansions expected to add thousands of employees over the coming years.
• 
  
• Partner closely with executive leadership, including a recently hired CFO who is committed to investing in the payroll team and infrastructure.
• 
  
• Take ownership of payroll operations, time & attendance, compliance, controls, reporting, and process improvement initiatives.
• 
  
• Play a key role in enhancing and optimizing the organization's UKG environment and supporting ongoing payroll transformation efforts.
• 
  
• Step into a highly visible leadership role with the opportunity to make an immediate and lasting impact.
• 
  
• Relocation assistance available, including moving expenses, temporary housing, travel assistance, and additional support for out-of-state candidates.
• 
  
• Competitive compensation package including bonus potential and strong benefits.
• 
  

Director of Payroll Key Responsibilities:

• 
  
• Lead payroll operations for a workforce of 10,000+ employees across multiple states.
• 
  
• Ensure accurate and timely payroll processing while maintaining compliance with federal, state, and local regulations.
• 
  
• Oversee payroll staff, providing leadership, coaching, and professional development.
• 
  
• Manage complex union payroll requirements across multiple collective bargaining agreements.
• 
  
• Serve as the subject matter expert for UKG payroll and workforce management systems.
• 
  
• Drive payroll process improvements, automation initiatives, and internal control enhancements.
• 
  
• Partner with HR, Finance, and Operations leadership on payroll-related projects and strategic initiatives.
• 
  
• Oversee payroll tax compliance, audits, reporting, and year-end processes.
• 
  

Qualifications

• 
  
• 10+ years of progressive payroll leadership experience in a large, complex organization.
• 
  
• Experience overseeing payroll for 10,000+ employees.
• 
  
• Strong multi-state payroll expertise.
• 
  
• Significant union payroll experience with multiple CBAs.
• 
  
• Hands-on experience with UKG required; Kronos/Dimensions experience strongly preferred.
• 
  
• Demonstrated success leading payroll teams through change, growth, and process improvement initiatives.
• 
  
• CPP designation and/or Bachelor's degree preferred.
• 
  
• Strong leadership, communication, and project management skills.
• 
  

#LI-MV1
#INOCT2026