Remote Payroll Director | Union-Experienced Leader

Jobot; Chicago (IL); Remote; USD 103,000 - 152,000; Full time

Benefits offered by this job

Platinum Benefits

High visibility

Long-term engagement

Job summary

Jobot is seeking a Payroll Director to lead a large, multi-state payroll team and guide ongoing transformation for a major organization. This long-term contract role blends people leadership with hands-on payroll execution, reporting to senior payroll leadership while driving process improvements and partnering with HR, Finance, and cross-functional teams.

The ideal candidate has extensive experience in union payroll, complex regulatory compliance, and enterprise systems

Qualifications

• 15+ years of progressive payroll experience, including leadership responsibilities over large teams.
• 5+ years managing payroll teams in a complex, multi-state environment.
• Experience overseeing high-volume payroll operations for large employee populations (5,000+).
• Union payroll experience is required.
• Strong understanding of payroll tax regulations, compliance, and reporting.
• Experience leading payroll process improvements, organizational initiatives, or operational change.
• Comfortable balancing strategic leadership with hands-on payroll processing when necessary.
• Experience partnering with HR, Finance, and cross-functional business leaders.
• Proven ability to lead teams through periods of change while maintaining service levels.
• Strong written and verbal communication skills with the ability to provide clear updates to executive leadership.
• Highly organized, self-directed, and comfortable working with minimal oversight.
• Construction, field services, or project-based industry experience is helpful but not required.
• Experience with enterprise payroll systems such as UKG, Workday, ADP, Oracle, or similar platforms is preferred.

Responsibilities

• Lead and develop a payroll operations team supporting a large multi-state employee population.
• Oversee payroll processing activities, ensuring accuracy, compliance, and timely execution.
• Provide coaching, direction, and workload management across the payroll team.
• Partner with payroll leadership on process improvements and operational initiatives.
• Support organizational change efforts and shared services projects.
• Lead cross-functional initiatives involving payroll, HR, finance, and operational stakeholders.
• Help evaluate and improve payroll workflows, controls, and service delivery processes.
• Monitor payroll tax activities and support transition-related initiatives as needed.
• Serve as an escalation point for complex payroll issues.
• Communicate project updates, risks, and recommendations to leadership.

Skills

Payroll leadership

Multi-state payroll

Union payroll

Process improvement

Stakeholder communication

Tools

UKG

Workday

ADP

Oracle

Job description

Jobot is seeking a Payroll Director to lead a large, multi-state payroll team and guide ongoing transformation for a major organization. This long-term contract role blends people leadership with hands-on payroll execution, reporting to senior payroll leadership while driving process improvements and partnering with HR, Finance, and cross-functional teams.

The ideal candidate has extensive experience in union payroll, complex regulatory compliance, and enterprise systems