Payroll Director | 10,000+ Employee Workforce

Creative Financial Staffing, LLC; Boston (MA); Hybrid; USD 170,000 - 190,000; Full time

Benefits offered by this job

Relocation assistance

Bonus potential

Competitive benefits

Job summary

Creative Financial Staffing, LLC is seeking a Director of Payroll in Boston, MA (Hybrid) to lead a complex, 10,000+ employee payroll operation. The role focuses on UKG systems, multi-state compliance, and ongoing process improvements.

With $170,000-$190,000 base salary plus bonus and relocation assistance, this position offers strategic influence, relocation support, and a path to transform payroll infrastructure within a large, unionized environment.

Qualifications

• 10+ years of progressive payroll leadership experience in a large 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; Kronos/Dimensions preferred.
• CPP designation and/or Bachelor’s degree preferred.
• Strong leadership, communication, and project management skills.

Responsibilities

• Lead payroll operations for a workforce across multiple states.
• Ensure accurate and timely payroll processing while compliant with regulations.
• Oversee payroll staff with leadership, coaching, and development.
• Manage union payroll requirements across multiple CBAs.
• Serve as SME for UKG payroll and workforce management systems.
• Drive payroll process improvements, automation, and internal control enhancements.
• Partner with HR, Finance, and Operations on payroll-related projects.
• Oversee payroll tax compliance, audits, reporting, and year-end processes.

Skills

Payroll leadership

Multi-state payroll

Communication skills

Project management

Education

CPP designation

Bachelor’s degree

Tools

UKG/Kronos Systems

Job description

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.