Senior Employment Counsel

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 We’re hiring a Senior Employment Counsel to be a core member of Sierra’s legal team. We are looking for someone who has deep expertise in employment and labor matters, including global employment/HR matters. You will thrive in dynamic environments, enjoy tackling challenges beyond your comfort zone, and be excited to contribute across the business. In return, we’ll provide the support and opportunities you need to grow and excel as a lawyer. You’ll be part of a legal team that is highly respected within both the company and the broader legal industry—committed to excellence, collaboration, and making a meaningful impact. Employment and Labor Counseling: Serve as the primary employment law advisor to Sierra's People team and business leaders on a broad range of employment and labor matters, including recruiting and hiring, employee relations, performance management, terminations and separations, wage and hour compliance, leaves of absence, accommodations, immigration, secondments, and employee classification. Employment Agreements; Playbooks: Draft, negotiate, and advise on employment‑related documents, including offer letters, PIIAs, separation and release agreements, equity documentation, and compensation plans. Develop and maintain policies, templates, and playbooks to drive consistency and speed at scale. Compensation and Equity: Advise on employment aspects of equity compensation programs, including offer letters and compensation structuring, tax considerations, and international plan mechanics. Scaling: Support employment law matters across Sierra's international offices, working with local outside counsel to ensure jurisdictional compliance while maintaining alignment with global People practices and guidelines. Partnership: Collaborate closely with the People, Finance, and business teams to support hiring, organizational change, and scaling in a high‑growth environment. Develop and deliver training programs on employment law topics for People team members, managers, and employees. What you’ll bring 6+ years of legal experience, with a combination of large law firm and in‑house experience at a tech company. Demonstrated depth in US state and federal employment law and broad US employment matters. Experience advising on international employment across multiple jurisdictions, with exposure to UK, EU, APAC, and/or LatAm employment law strongly preferred. Excellent drafting skills and the ability to produce clean, business‑ready employment documents with minimal supervision. Strong judgment and the ability to operate as a trusted advisor to HR and business leaders, translating legal risk into practical, actionable guidance. Comfortable working in ambiguity and at pace, able to prioritize competing demands, manage a high volume of matters, and push work forward with minimal supervision. A proactive mindset and genuine interest in building processes and infrastructure in a fast‑paced, dynamic startup environment. Teamwork: A team player first and foremost, with a low‑ego willingness to pitch in on each day’s new challenges. Sierra is a unique place to work, with a strong sense of togetherness, and the legal team is no exception. You will look out for your colleagues and be accustomed to sharing and helping the team succeed. As the team grows, you will train and mentor more junior members. Judgment: Understand risk in the context of a hyperscaling business, have sound judgment, and be strategic in your decision‑making. You will not be afraid to make judgment calls, and you will be empowered to do so. Approach: A strong work ethic with an eye for detail. You will strive for perfection and expect that of others. Collaborate: Collaborate cross‑functionally with Sales, Operations, and Agent Development teams to support revenue growth and strategic business initiatives. A passion for AI, with a deep understanding of AI products, LLMs, and the related legal issues, and personal experience with integrating AI into your work. Significant law firm experience at a top‑tier, internationally recognized law firm. Experience working at and scaling a global employment/HR program at a high‑growth technology company. Experience with international equity compensation mechanics and other non‑US employee equity programs. 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 one another, both 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, respect, and celebrate each other’s personal and professional achievements. We want our benefits to reflect our values and offer the following to full‑time employees: Compensation: $225K – $275K + Offers Equity Flexible (Unlimited) Paid Time Off Medical, Dental, and Vision benefits for you and your family Life Insurance and Disability Benefits Retirement Plan (e.g., 401K, pension) with Sierra match 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 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