Payroll Director

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

Payroll Director

$75 - $110 per hour | Chicago, IL | Remote | Consulting

REMOTE + MUST HAVE union experience & strong leadership, Great Company, High Growth, Platinum Benefits (low deductible, medical/dental/vision/401k/sick time within 30 days of starting

A bit about us:

We are a publicly traded, market-leading company operating through a large network of entrepreneurial business units across North America and internationally. Our leadership culture is centered around accountability, ownership, continuous improvement, and developing great leaders.

Why join us?

• Platinum Benefits (low deductible, medical/dental/vision/401k/sick time within 30 days of starting)
• Lead an established payroll team supporting a large, complex workforce.
• High visibility role with direct access to senior payroll leadership.
• Opportunity to influence payroll operations during a period of organizational evolution.
• Balance people leadership, operational ownership, and project work.
• Long-term engagement expected through at least 2027.
• Work for a large, financially stable organization that continues to invest in its people, systems, and processes.
• Ability to make a meaningful impact without being buried in layers of bureaucracy.

Job Details

We are seeking a 2+ year long-term, contract, Payroll Director to provide leadership for an established payroll operations team supporting a large, multi-state employee population. This individual will oversee day-to-day payroll administration for a $1B business and 15 direct reports, drive process improvements, support organizational initiatives, and serve as a key partner to payroll leadership during an ongoing operational transformation.

The ideal candidate is a hands‑on payroll leader who can effectively manage a team, navigate complex payroll environments, and independently drive priorities forward with minimal oversight. This role offers a blend of people leadership, operational execution, and project ownership.

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.

Requirements

• 15+ years of progressive payroll experience, including leadership responsibilities over large teams
• 5+ years managing payroll teams in a complex, multi-state environment.
• Demonstrated 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.

What We're Looking For

• A leader who enjoys coaching and developing teams while remaining willing to roll up their sleeves when needed.
• Someone who creates structure in fast-moving environments and keeps priorities organized.
• A proactive communicator who keeps stakeholders informed without being asked.
• A manager who can independently execute initiatives while partnering closely with senior leadership.
• Someone who thrives in organizations experiencing growth, change, and continuous improvement.

Jobot is an Equal Opportunity Employer. We provide an inclusive work environment that celebrates diversity and all qualified candidates receive consideration for employment without regard to race, color, sex, sexual orientation, gender identity, religion, national origin, age (40 and over), disability, military status, genetic information or any other basis protected by applicable federal, state, or local laws. Jobot also prohibits harassment of applicants or employees based on any of these protected categories. It is Jobot’s policy to comply with all applicable federal, state and local laws respecting consideration of unemployment status in making hiring decisions.

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