Payroll Director

DeWinter BH; 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

Payroll Director

Overview

Lead the future of payroll operations for a complex North American organization supporting more than 10,000 employees across multiple locations and a heavily unionized workforce. The Payroll Director will oversee end-to-end U.S. payroll delivery, lead and develop a high-performing payroll organization, ensure compliance with numerous Collective Bargaining Agreements (CBAs), and drive system modernization, automation, and continuous improvement.

This strategic leadership opportunity is ideal for a technically strong payroll executive who can balance operational excellence with innovation, build trusted cross-functional partnerships, and establish scalable payroll practices across a complex enterprise environment.

Required Skills

• 10+ years of progressive payroll management experience within a large, complex North American organization of 10,000+ employees
• 6+ years of experience managing and developing skilled payroll teams
• Bachelor’s degree or Certified Payroll Professional (CPP) designation
• Extensive experience delivering payroll services in a heavily unionized environment with multiple CBAs
• Strong understanding of federal, state, and local payroll tax regulations, labor laws, compliance requirements, and internal controls
• Proven success implementing and managing large, multi-location U.S. payroll providers
• Experience leading complex, cross-functional payroll projects and organizational change initiatives
• Strong expertise in time and attendance auditing, time control, leave tracking, and reporting
• Demonstrated ability to align payroll systems and workflows with complex labor agreements
• Exceptional verbal, written, interpersonal, analytical, and business-partnering skills
• Strong leadership, coaching, problem-solving, and decision-making capabilities
• Ability to manage biweekly and semimonthly payroll operations with a high degree of accuracy and confidentiality

Nice to Have Skills

• Experience with UKG HCM and payroll platforms
• Strong experience with UKG Workforce Management, Kronos/Dimensions, and UTA
• Transit industry experience
• Experience supporting payroll operations for a workforce governed by complex CBAs
• Background in business process digitalization and automation, including AI implementation
• Experience developing payroll performance metrics, KPIs, and advanced reporting capabilities
• Bilingual proficiency in English and French
• Experience managing year-end tax activities, including W-2s, 1042-S, T4s, and Records of Employment

Preferred Education and Experience

• Bachelor’s degree in accounting, finance, business administration, human resources, or a related field; CPP certification may be considered in place of a degree
• 10+ years of progressive payroll experience
• 6+ years leading payroll teams in a large, multi-location organization
• Experience supporting a complex, unionized workforce with multiple payroll cycles and labor agreements

Other Requirements

• Remote or hybrid position; candidates located in the Boston area are preferred for a hybrid schedule of approximately 2–3 days onsite per week
• Fully remote consideration requires strong UKG expertise and the ability to work Eastern Time hours
• Standard working hours are 8:00 a.m.–5:00 p.m. Eastern Time
• Must be willing to work outside standard hours periodically to support California payroll processing
• Must be able to manage confidential payroll information with discretion and maintain rigorous data security standards
• Must be comfortable partnering with payroll, time and attendance, finance, human resources, and operational teams across multiple locations
• Business casual work environment for onsite employees