Director of Payroll

About the role

You'll own US and Canada payroll operations end-to-end — hands-on in Workday, close to the details — while also managing and developing 1–2 direct reports on the US team. You'll report directly to the Head of Global Payroll and be a key leader in making sure North American payroll keeps pace with Anthropic's growth.

Strategic importance: You'll be a key contributor to our compliance initiative — our framework for managing payroll tax obligations across US & Canada. You'll also be part of the team driving AI adoption within payroll: we're actively building out how AI tools can improve reconciliation accuracy, error detection, and reporting workflows. This isn't a future initiative — it's happening now.

Responsibilities

US Payroll Operations

• Own full-cycle payroll processing for all US entities — multi-state, multi-frequency, exempt and non-exempt populations
• Process complex equity compensation including RSUs, ISOs, and NSOs, ensuring accurate tax withholding and timely reporting
• Manage high-volume payments: bonuses, commissions, severance, and equity events
• Oversee quarter-end, W-2 preparation, year-end reconciliations, and resolution of federal and state tax notices
• Maintain and continuously improve Workday payroll configuration — identify automation opportunities and lead optimization initiatives

Canada Payroll Management

• Oversee Canada payroll operations in partnership with our PwC Global Payroll Platform, developing expertise in CRA compliance, T4s, Records of Employment, and multi-province processing
• Partner with our international payroll team to ensure Canada stays integrated into our global compliance posture
• Build out Canada payroll SOPs as the function matures

Team Leadership & Development

• Manage and develop 1–2 direct reports on the US payroll team — set clear expectations, provide regular feedback, and invest in their growth
• Build a team culture of accuracy, accountability, and continuous improvement
• Serve as the escalation point for complex payroll issues and employee inquiries

Cross-Functional Partnership & Compliance

• Partner with Corporate Accounting on payroll journal entries, accruals, and month-end close
• Work closely with Tax, Benefits, People Systems, and Employment Legal to ensure data integrity and compliance
• Support audit readiness and internal & systems controls

AI Adoption & Process Improvement

• Champion the use of AI tools within the payroll function — identify high-value use cases for reconciliation, anomaly detection, and reporting
• Lead or support process improvement projects that reduce manual effort, increase accuracy, and improve the employee payroll experience
• Document processes, build SOPs, and contribute to the team's knowledge infrastructure

You may be a good fit if you have

• 8+ years of payroll experience, with at least 3 years in a senior or manager-level role owning US multi-state payroll end-to-end
• Hold a CPP (Certified Payroll Professional) certification
• Direct people management experience — you've managed at least one FTE directly, not just contractors or mentorship relationships
• Strong Workday experience — payroll module preferred; HCM with direct payroll involvement and a clear path to Workday Payroll ownership is considered
• Deep familiarity with equity compensation processing (RSUs, ISOs, NSOs) and the tax implications at both federal and state levels
• Demonstrated ability to thrive in fast-moving, ambiguous environments — you build structure where none exists and don't wait for someone to hand you a playbook
• Strong cross-functional instincts — you know how to build trust quickly, influence without authority, and communicate clearly across Finance, HR, Legal, and beyond

Strong candidates may also have

• Canada payroll experience — even introductory exposure is valued; willingness to learn and grow into the function matters more than deep expertise on day one
• Experimented with AI or automation tools to improve payroll workflows (reconciliation, error detection, reporting)
• Been part of a Workday payroll implementation or major system migration
• Worked at a company that scaled rapidly — from 500 to 2,000+ employees — and built payroll infrastructure to match
• Experience in or exposure to IPO readiness, SOX compliance, or building financial controls from scratch