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Sierra is building an AI platform that enables enterprises to deliver better, more human customer experiences. The company partners with industry leaders like SoftBank, Uber, Rivian, CLEAR, and Sutter Health. Founded by Bret Taylor (former Salesforce co-CEO, Facebook CTO, Google Maps co-creator) and Clay Bavor (18-year Google veteran who led Google Labs and AR/VR initiatives), Sierra is primarily based in San Francisco with growing offices across North America, Europe, and Asia.
As Deal Operations Manager, you'll be the operational backbone of Sierra's enterprise sales motion, sitting at the intersection of Sales, Finance, Legal, and Product. You'll own end-to-end deal support—structuring pricing, building proposals, and running approval workflows for complex enterprise and strategic deals. Your responsibilities include partnering with Sales to design deal desk processes, discounting guardrails, and approval matrices that balance speed with governance; working cross-functionally with Legal, Finance, and Product to unblock non-standard terms and multi-year/multi-product deals; and building dashboards in Salesforce and Sheets to track pipeline, cycle time, and win/loss trends.
You'll analyze deal data to identify bottlenecks and recommend process improvements, support quote-to-cash processes ensuring accuracy in contract terms and revenue recognition handoffs, and own special projects around pricing strategy, packaging, and international deal structures. The role emphasizes leveraging AI-native tools (Claude Code, Cursor) to automate repetitive workflows and create scalable systems.
You'll bring 3+ years in deal desk, sales operations, revenue operations, or management consulting. Strong Excel/Sheets skills, financial modeling experience, and familiarity with Salesforce and contract/CLM tools (Ironclad, DocuSign) are essential. You're detail-oriented, can manage multiple live deals under pressure, communicate clearly with leadership, and have a proactive builder mentality comfortable creating processes in ambiguous, fast-moving environments.
