Payroll Lead

About us At Sierra, we’re building a platform to enable every company in the world to build better, more human customer experiences with AI. We partner with industry leaders such as SoftBank, Uber, Rivian, CLEAR, and Sutter Health. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. 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 company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. What we offer We want our benefits to reflect our values and offer the following to full-time employees: 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 These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. Be you, with us We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class. #J-18808-Ljbffr Sierra