Payroll Lead

About us At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New York, London, Paris, Madrid, Munich, Singapore, Tokyo, and Sydney. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor and Clay Bavor . Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. What you’ll do 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. 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. What you’ll bring 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. Even better… 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. Our values Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the comp