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 team, 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
- 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
- Certified Payroll Professional (CPP) designation 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
Key Responsibilities
- Oversee accurate and timely U.S. payroll delivery across multiple locations and entities
- Ensure compliance with federal, state, and local regulations, labor laws, internal controls, and applicable CBAs
- Serve as a functional subject matter expert for UKG HCM, Kronos/Dimensions, UTA, and related payroll systems
- Lead time and attendance oversight, including system configuration, workflow alignment, audits, leave tracking, and reporting
- Drive payroll digitalization, automation, and continuous improvement initiatives, including the evaluation of AI-enabled solutions
- Develop performance metrics, KPIs, reporting capabilities, and business cases for system enhancements
- Lead year-end payroll and tax activities, including W-2s, 1042-S, T4s, and Records of Employment
- Coach and develop the payroll team while providing cross-functional guidance to related payroll functions
- Build strong partnerships with finance, human resources, time and attendance, and operational teams across multiple locations
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 candidates must have strong UKG expertise and be able 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 manage confidential payroll information with discretion and maintain rigorous data security standards
- Must be comfortable collaborating with teams across multiple locations
- Business casual work environment for onsite employees
- Contract duration of 6+ months
