Payroll Lead

Sierra • San Francisco, CA

1d • $190,000 - $225,000 • Onsite

About The Position

At Sierra AI, we’re building a fast-scaling company where clarity, excellence, and a world-class employee experience matter deeply. As our Payroll Manager, you will own and evolve Sierra’s global payroll operations, ensuring accuracy, compliance, and an exceptional experience for employees across multiple regions. You’ll design scalable systems, partner closely with Finance and People teams, and help build the foundation that supports Sierra’s growth.

Requirements

• 10+ years of payroll experience, ideally within high-growth, global technology companies.
• Strong understanding of U.S. multi-state payroll, as well as experience supporting international payroll (EMEA and/or APAC preferred).
• Expertise in payroll compliance, tax regulations, and year-end filings (W-2s, 1099s, bonuses, equity withholding, etc.).
• Experience working with payroll and HR systems such as ADP, Gusto, Rippling, Workday, Deel, or similar.
• Excellent analytical skills with a high level of accuracy, attention to detail, and strong documentation habits.
• Clear communicator with the ability to partner effectively with executives, Finance, Legal, and employees at all levels.
• A proactive, systems-minded approach excited to build and improve processes in a fast-paced, scaling environment.

Nice To Haves

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

Responsibilities

• Manage end-to-end global payroll operations across the U.S. and international regions, ensuring timely, accurate, and compliant payroll processing.
• Build scalable payroll systems and workflows, partnering with Finance, People Ops, and Legal to automate processes, maintain data integrity, and support company growth.
• Ensure full payroll compliance with federal, state, and international regulations, including tax filings, statutory requirements, audits, and year-end reporting.
• 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.
• Analyze payroll data and maintain documentation, using insights to forecast costs, drive process improvements, and support global expansion and workforce planning.

Benefits

• Flexible (unlimited) paid time off
• Medical, dental, and vision benefits for you and your family
• Life insurance and disability benefits
• Retirement plan dependent on country of employment
• Parental leave
• Fertility and family building benefits through Carrot
• Lunch, as well as delicious snacks and coffee to keep you energized
• Discretionary benefit stipend giving people the ability to spend where it matters most
• Free alphorn lessons

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed