About this role
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.
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.
WHAT YOU'LL DO
Sierra’s outcomes-based pricing model is central to how we partner with customers. In this role, you will work with senior leaders across Sales, Operations, Product, Finance, and Legal. You will help negotiate complex partnerships with Fortune 500 companies, build business cases that demonstrate Sierra’s value, and shape pricing strategies for AI agents that drive revenue, improve retention, and transform core business processes.
- Lead pricing strategy for major enterprise opportunities, from early customer discussions through negotiation and close
- Develop commercial models and ROI analyses that connect Sierra’s performance to measurable customer value
- Bring clear analysis and sound judgment to high-stakes customer negotiations
- Partner across the company to turn new product capabilities into scalable commercial offerings
WHAT YOU'LL BRING:
- 4+ years of experience in consulting, banking, strategy, or business operations. Startup experience in a similar GTM operations role, specifically SaaS pricing, sales, marketing, and operations strongly preferred.
- Experience negotiating complex customer partnerships and familiarity with navigating sales cycles
- Strong financial modeling skills and the ability to turn analysis into a clear executive recommendation
- Excellent commercial judgment, including the ability to make thoughtful decisions with incomplete information
- Clear written and verbal communication with senior leaders
- Degree in Business Administration, Finance, or related field, or equivalent professional experience
EVEN BETTER...
- Experience in partnerships, business development, and value engineeri