Director, Payroll & Benefits

Director, Payroll & BenefitsWe are looking for a strategic and operational leader to oversee our North American payroll and benefits function. With a growing footprint across the US (FL, AZ, NV, and remote states) and Canada (Headquartered in Manitoba), we need an expert capable of navigating cross-border complexities. You will lead a team of six to ensure flawless bi-weekly execution while driving process improvements, ensuring strict compliance across multiple jurisdictions, and managing a comprehensive benefits portfolio. As Director, Payroll & Benefits, you will Manage, coach, and develop a team of 6 (Payroll Manager, Analyst, and Admins), fostering a culture of accuracy, confidentiality, and customer service. Design payroll and benefits processes that can scale with the company's growth, including potential M&A activity or expansion into new states/provinces. Own the relationships with HRIS/Payroll provider (Dayforce) and benefits brokers in both countries, negotiating contracts and SLAs. Oversee the end-to-end processing of bi-weekly payrolls for all salaried and hourly employees across the US and Canada. Manage Multi-Jurisdictional Complexity: Canada: Oversee provincial remittances, with a specific focus on Manitoba Employment Standards and the HE Levy (Health and Post Secondary Education Tax Levy). USA: Manage multi-state payroll rules, specifically handling employees in Florida, Arizona, and Nevada. Partner with Finance to ensure accurate General Ledger recording, month-end accruals, and timely reconciliation of payroll accounts. Oversee administration of 401(k) audits, Open Enrollment, ACA compliance (Form 1095-C), and self-insured vs. fully insured health plan analysis. Manage supplemental health plans, ensuring alignment with provincial coverage. Oversee the interaction between company leave policies and state/provincial programs (e.g., FMLA, ADA in the US; EI sickness/maternity and Employment Standards leaves in Canada). Serve as the primary point of contact for external audits (workers' comp, 401k/RRSP, IRS/CRA inquiries). Direct the Payroll Analyst in routine internal audits to validate data integrity, catch anomalies before finalization, and ensure internal control compliance. Monitor changes in legislationsuch as changes to the Manitoba vacation pay rules or US state-specific pay transparency and sick leave lawsand update internal policies and processes accordingly. Own the Year-End process, ensuring accurate production and distribution of W-2s, 1095s, T4s, and T4As. As Director, Payroll & Benefits, you need Bachelor's degree in Accounting, Finance, HR, or related field. 10+ years of payroll experience, with at least 5 years in a leadership role managing a team. Experience managing both US (multi-state) and Canadian payrolls simultaneously is highly preferred. Education: Certifications: US: Certified Payroll Professional (CPP) highly preferred. Canada: National Payroll Institute (PCP or CPM) designation highly preferred. Advanced proficiency in HRIS/Payroll systems (Dayforce / others). Ability to switch mindsets between US "At-Will" employment concepts and Canadian "Common Law" requirements. An understanding of the tax implications of "work from anywhere" policies (e.g., establishing a business presence in a new state). Ability to look beyond the "what" (paying people) to the "why" (analyzing labor costs, overtime trends, and benefit utilization).