Director of Payroll - Hybrid

WeDriveU

$125K — $150K *
Transportation
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 10+ years of payroll leadership experience in complex, multi-entity organizations.
  • 5+ years managing union payroll, ideally in transportation, hospitality, or travel.
  • Proven experience leading implementation of new HR and payroll platforms.
  • Strong working knowledge of collective bargaining agreements and compliance.
  • Expertise with cloud-based payroll systems like ADP, Kronos, Workday, or UKG.
  • Advanced proficiency in Google Workspace and project management tools.
  • Strong understanding of FLSA, wage and hour laws, and tax regulations.

Responsibilities

  • Lead payroll teams to ensure accurate and timely processing across multiple regions.
  • Manage union benefit contributions and compliance with collective bargaining agreements.
  • Oversee payroll governance and internal controls for regulatory compliance.
  • Partner with HR, Finance, and IT to streamline payroll processes and systems integration.
  • Drive continuous improvement and implement solutions to operational challenges.
  • Maintain current Standard Operating Procedures (SOPs) aligned with business needs.
  • Stay updated on payroll legislation and communicate changes to stakeholders.

Benefits

  • Exceptional Medical, Dental, Vision, and Life Insurance benefits.
  • Competitive compensation packages with unlimited PTO.
  • 401(k) with 4% employer match.
  • Financial Wellness Tool and Commuter Benefits.
  • Employee Assistance Program (EAP).
  • Paid holidays and Pet & Legal Insurance.
  • On-the-job training and internal transfer opportunities for career growth.
Full Job Description
About the Role

WeDriveU is looking for a Payroll Director to lead our payroll operations supporting a diverse, multi-state workforce that includes both union and non-union employees. This role is responsible for overseeing all payroll functions, both strategic and day-to-day, while ensuring accuracy, compliance, and alignment with collective bargaining agreements and legal requirements. The ideal candidate will bring deep expertise in union payroll, system integrations, and process improvement, with a focus on building a collaborative and high-performing team.

What You'll Do

  • Lead payroll teams to ensure accurate and timely processing across multiple divisions and regions.
  • Manage union benefit contributions, wage deductions, and compliance with collective bargaining agreements.
  • Oversee payroll governance and internal controls to ensure compliance with all federal, state, and local regulations.
  • Partner with HR, Finance, and IT to streamline processes and integrate payroll systems across the organization.
  • Drive continuous improvement and implement solutions to operational challenges, ensuring issues are resolved quickly and effectively.
  • Maintain current Standard Operating Procedures (SOPs) and ensure alignment with evolving business needs.
  • Stay up to date on changes in payroll legislation and communicate key updates to employees and business partners.
  • Lead with a focus on efficiency, innovation, and employee experience.

What You Bring

  • Demonstrated experience with Workday implementation and optimization, along with a strong background in national payroll operations and processes.
  • 10+ years of payroll leadership experience in complex, multi-entity organizations.
  • 5+ years managing union payroll, preferably within transportation, hospitality, or travel industries.
  • Proven experience leading the implementation of a new enterprise HR and payroll platform, driving data integrity, automation, and process improvement at scale
  • Strong working knowledge of collective bargaining agreements and related compliance.
  • Expertise with cloud-based payroll systems and HRIS platforms such as ADP, Kronos, Workday, or UKG.
  • Advanced proficiency in Google Workspace and project management tools.
  • Strong understanding of FLSA, wage and hour laws, and tax regulations.
  • Proven track record of developing high-performing teams and scalable payroll operations.
  • Excellent communication, collaboration, and problem-solving skills.

Preferred Qualifications

  • ADP experience is preferred
  • Experience with Workday
  • Certified Payroll Professional (CPP) designation.
  • Experience interpreting and implementing union agreements.
  • Experience leading payroll integrations following acquisitions or system migrations.


We Offer

Physical Health

  • Exceptional Medical, Dental, Vision, and Life Insurance benefits

Financial Health

  • Competitive compensation packages-including base salary, bonus, and benefits-along with unlimited PTO.
  • 401(k) with 4% employer match
  • Financial Wellness Tool
  • Commuter Benefits

Emotional Health

  • Employee Assistance Program (EAP)
  • Unlimited PTO
  • Paid holidays
  • Pet & Legal Insurance

Personal Development

  • On-the-job training and skills development
  • Internal transfer opportunities for career growth

*Benefits vary by position and location

Similar Jobs

More Jobs at WeDriveU

More Transportation Jobs

Find similar Director of Payroll - Hybrid jobs: