Deal Operations Manager

At Sierra, we’re building a platform to enable every company in the world to build better, more human customer experiences with AI. We partner with industry leaders such SoftBank, Uber, Rivian, CLEAR, and Sutter Health. 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 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.

We're looking for a Deal Operations Manager to sit at the intersection of Sales, Finance, Legal, and Product, helping structure, price, and close complex enterprise deals. You'll be the operational backbone of our sales motion — ensuring deals move quickly, accurately, and profitably from proposal to signature.

Own end-to-end deal support: structuring pricing, building proposals, and running approval workflows for enterprise and strategic deals. Partner with Sales to design and maintain deal desk processes, discounting guardrails, and approval matrices that balance speed with governance. Work cross-functionally with Legal, Finance, and Product to unblock non-standard terms, custom packaging, and multi-year/multi-product deals. Build and maintain tools/dashboards (Salesforce, Sheets, or internal systems) to track deal pipeline, cycle time, and win/loss trends. Analyze deal data to identify bottlenecks in the sales cycle and recommend process improvements. Support quote-to-cash processes, ensuring accuracy in contract terms, billing setup, and revenue recognition handoffs. Own special projects related to pricing strategy, packaging, discounting policy, and international deal structures. Leverage AI-native tools (e.g., Claude Code, Cursor) to automate repetitive deal workflows and create scalable systems.

3+ years of experience in deal desk, sales operations, revenue operations, or management consulting. Strong Excel/Google Sheets skills; comfort with financial modeling and deal economics (discounting, margin, ARR impact). Experience with CRM platforms (Salesforce preferred) and contract/CLM tools (e.g., Ironclad, DocuSign). High attention to detail — you catch pricing errors and contract inconsistencies before they become problems. Ability to manage multiple live deals simultaneously under time pressure without sacrificing accuracy. Strong written and verbal communication skills; comfortable presenting recommendations to Sales leadership and executives. A proactive, builder mentality — comfortable creating process from scratch in an ambiguous, fast-moving environment.

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