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About the Role
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.
Responsibilities
- 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.
Requirements
- 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.
Skills
- Excel
- Google Sheets
- Financial modeling
- Deal economics
- Salesforce
- Contract/CLM tools
- Ironclad
- DocuSign
- Written communication
- Verbal communication
- AI-native tools
- Claude Code
- Cursor
Location
- San Francisco
Work Type
- In-person
Experience Level
- 3+ years
Benefits
- Flexible (unlimited) paid time off
- Medical, dental, and vision benefits for you and your family
- Life insurance and disability benefits
- Retirement plan dependent on country of employment
- Parental leave
- Fertility and family building benefits through Carrot
- Lunch, as well as delicious snacks and coffee
- Discretionary benefit stipend
- Free alphorn lessons
- Equity plans
About the Company
- Sierra is building a platform to enable every company 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.
- Our co-founders are Bret Taylor and Clay Bavor.
- Bret Taylor's background includes Board Chair of OpenAI, co-CEO of Salesforce, CTO of Facebook, and co-creator of Google Maps.
- Clay Bavor spent 18 years at Google, leading Google Labs, AR/VR effort (Project Starline), Google Lens, and product/design teams for Google Workspace.
Equal Opportunity
- 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.