Payroll Lead

Sierra Sierra · AI Frontier · San Francisco, CA · Operations

Sierra AI is building a platform to help businesses build better, more human customer experiences with AI. This role is for a Payroll Lead who will own and evolve Sierra’s global payroll operations, ensuring accuracy, compliance, and an exceptional experience for employees across multiple regions. The role involves designing scalable systems, partnering with Finance and People teams, and building the foundation for company growth.

What you'd actually do

  1. Manage end-to-end global payroll operations across the U.S. and international regions, ensuring timely, accurate, and compliant payroll processing.
  2. Build scalable payroll systems and workflows, partnering with Finance, People Ops, and Legal to automate processes, maintain data integrity, and support company growth.
  3. Ensure full payroll compliance with federal, state, and international regulations, including tax filings, statutory requirements, audits, and year-end reporting.
  4. Serve as a trusted advisor to employees and leaders, providing clear guidance on payroll, taxes, and equity, while managing third-party vendors for quality and accuracy.
  5. Analyze payroll data and maintain documentation, using insights to forecast costs, drive process improvements, and support global expansion and workforce planning.

Skills

Required

  • 10+ years of payroll experience
  • Strong understanding of U.S. multi-state payroll
  • experience supporting international payroll
  • Expertise in payroll compliance, tax regulations, and year-end filings
  • Experience working with payroll and HR systems such as ADP, Gusto, Rippling, Workday, Deel, or similar
  • Excellent analytical skills
  • Clear communicator
  • proactive, systems-minded approach

Nice to have

  • Experience supporting global expansion and new entity setup
  • Familiarity with equity compensation
  • CPP (Certified Payroll Professional) or similar certification
  • Experience designing or managing scalable payroll audits and controls

What the JD emphasized

  • global payroll operations
  • scalable payroll systems and workflows
  • full payroll compliance
  • trusted advisor
  • Analyze payroll data