Director of Payroll - Hybrid

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. 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. Stay up to date on changes in payroll legislation and communicate key updates to employees and business partners. 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. ~ 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. ~ Experience with Workday or UKG. Certified Payroll Professional (CPP) designation. Experience interpreting and implementing union agreements. Experience leading payroll integrations following acquisitions or system migrations. Exceptional Medical, Dental, Vision, and Life Insurance benefits ~ Competitive compensation packages—including base salary, bonus, and benefits—along with unlimited PTO. ~Financial Wellness Tool ~ Employee Assistance Program (EAP) ~ Paid holidays ~ Pet & Legal Insurance ~ On‑the‑job training and skills development ~ We celebrate diversity and are committed to creating an inclusive environment free of discrimination or harassment where thoughts and ideas of all employees are appreciated and respected. We also see diversity as more than policies;