Senior Commercial Counsel

San Francisco · 6+ years experience · Full-time · Onsite · Posted Oct 14, 2026

At a glance

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.
Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. 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.

Sierra is hiring a Senior Commercial Counsel to be a core member of the legal team.
The role focuses on commercial contracts while offering opportunities to broaden scope across IP, regulatory, and product.
The position operates in a dynamic environment supporting revenue growth and strategic business initiatives.

Structure, negotiate and advise on all commercial contracts, including SaaS subscription agreements, technology licenses, professional services agreements, channel partner agreement, vendor agreements and NDAs.
Help build out the commercial function to be best in class by developing templates, playbooks, and workflows to drive efficiency and scalability.
Apply deep knowledge of practice areas that underpin the commercial practice, including contract law, IP and privacy, and advise on AI-related legal nuances and evolving regulatory frameworks.
Look out for colleagues, share knowledge, help the team succeed, and train and mentor more junior team members as the team grows.
Understand risk in the context of a hyper-scaling business, exercise sound judgment, make strategic decisions, and make judgment calls.
Maintain a strong work ethic with an eye for detail, striving for perfection.
Collaborate cross-functionally with Sales, Operations, and Agent Development teams to support revenue growth and strategic business initiatives.

6+ years of legal experience, with a combination of both large law firm and in-house experience at a tech company.
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.

Commercial privacy and security contracting experience (e.g., DPAs, BAAs, security agreements).
Experience of privacy/regulatory frameworks and ability to 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.