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Commercial Counsel (New York, NY - onsite)

About Sierra

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, Japan, 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 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 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.

Responsibilities

• Commercial Contracting: Structure, negotiate, and advise on all commercial contracts, including SaaS subscription agreements, technology licenses, professional services agreements, channel partner agreements, 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 and be accustomed to sharing and helping the team succeed.
• 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.

Requirements

• 2-6 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 (verbal and written) 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 with 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.
• 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.

Sierra values

• Trust: We build trust with our customers through 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.

Compensation & Benefits

We want our benefits to reflect our values and offer the following to full-time employees:

• Compensation: $220K – $250K + 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
• Parental Leave
• Fertility and family building benefits through Carrot
• Lunch, as well as delicious snacks and coffee to keep you energized
• Discretionary Benefit Stipend gives 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.

Sierra has exclusively engaged Kerwin Associates to conduct this search. Any resumes sent directly to Sierra will be forwarded to Kerwin Associates. If interested in this role, please contact Anne Kerwin Payne (anne@kerwin.com) and Spencer Britschgi (spencer@kerwin.com) at Kerwin Associates.