Payroll Director - Remote/Hybrid, Unionized Payroll Ops

DeWinter Group; Boston (MA); Hybrid; USD 150,000 - 190,000; Full time

Job summary

DeWinter Group is seeking a Payroll Director to lead end-to-end U.S. payroll for a large, multi-location organization with a heavily unionized workforce.

You will build and mentor a high-performing payroll team while driving system modernization, automation, and process improvements across the enterprise. The role requires extensive expertise in payroll regulations, CBAs, and cross-functional collaboration to ensure accurate, timely payroll delivery and strong internal controls.

Qualifications

• 10+ years of progressive payroll management experience in a large North American organization.
• 6+ years leading payroll teams and developing staff.
• Bachelor’s degree or CPP designation.
• Extensive experience delivering payroll in a heavily unionized environment with multiple CBAs.
• Strong knowledge of federal, state, and local payroll regulations, labor laws, compliance requirements, and internal controls.

Responsibilities

• Oversee end-to-end U.S. payroll delivery for a multi-location enterprise.
• Lead and develop a high-performing payroll organization.
• Drive system modernization, automation, and continuous improvement of payroll processes.
• Ensure compliance with CBAs and labor agreements across locations.
• Partner with cross-functional teams including finance, HR, and operations.

Skills

Payroll leadership

Team development

Regulatory compliance

Cross-functional collaboration

Change management

Time & attendance auditing

Confidential data handling

Payroll systems

Education

Bachelor’s degree

CPP certification

Tools

UKG HCM

UKG Workforce Management

Kronos/Dimensions

UTA

Job description

DeWinter Group is seeking a Payroll Director to lead end-to-end U.S. payroll for a large, multi-location organization with a heavily unionized workforce.

You will build and mentor a high-performing payroll team while driving system modernization, automation, and process improvements across the enterprise. The role requires extensive expertise in payroll regulations, CBAs, and cross-functional collaboration to ensure accurate, timely payroll delivery and strong internal controls.