Senior Commercial Counsel

About us

Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. 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 a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.

Sierra was co-founded by Bret Taylor and Clay Bavor who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs.

What you’ll do

We’re hiring a Senior Commercial Counsel to be a core member of Sierra’s legal team. We are looking for someone who has deep expertise in commercial contracts, but also someone who is also eager to broaden their scope across IP, regulatory, and product. 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.

• Commercial Contracting: Structure, negotiate and advise on all commercial contracts, including SaaS subscription agreements, technology licenses, professional services agreements, channel partner agreement, vendor agreements and NDAs. Commercial privacy and security contracting experience (e.g., DPAs, BAAs, security agreements) is a plus.

• Operational Excellence: Help build out our commercial function to be best in class. We aim to be the fastest and strongest, where the legal team is the differentiator in the contract lifecycle. You will be developing templates, playbooks, and workflows to drive efficiency and scalability.

• Expertise: Deep knowledge of practice areas that underpin the commercial practice, including contract law, IP and privacy. You will also want to work in AI and understand the nuances of law as it relates to AI, including the evolving regulatory frameworks. You will be expected to advise broadly on all contractual issues and be comfortable doing so.

• Teamwork: A team player first and foremost. 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, be accustomed to sharing and helping the team succeed. As the team grows, you will train and mentor more junior members.

• Judgement: Understand risk in the context of a hyper-scaling business, have sound judgement and be strategic in your decision making. You will not be afraid to make judgement 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.

What you’ll bring

• 6+ years of legal experience, with a combination of both large law firm and in-house experience at a tech company. While we are looking for a Senior Legal Counsel, we are open to considering exceptional candidates with less experience as Commercial Counsel.

• A strong background in negotiating and managing complex commercial contracts, preferably in SaaS, AI, or enterprise software.

• Strong communication skills and the ability to partner with both legal and non-legal stakeholders.

• A proactive mindset and the ability to navigate ambiguity in a fast-paced, dynamic startup environment.

Even better…

• Experience of privacy/regulatory frameworks and can advise on data processing agreements and security-related contract provisions.

• A passion for AI, with a deep understanding of AI products, LLMs and the related legal issues.

• Significant law firm experience at a top-tier, internationally recognized law firm.

• Experience working at a high-growth startup and operating with a sense of ownership.

• Industry specific knowledge in any of the following: Financial Services, Healthcare, Telecoms, Insurance and/or Consumer.

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

• Lunch, as well as delicious snacks and coffee to keep you energized when working onsite

• 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 employment type, 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 through the link on this page even if your experience doesn't precisely match the job description.

Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at [email protected]. Requests are handled confidentially and do not affect your candidacy.

We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.