Deal Operations Manager
Role Summary
Join Sierra as a Deal Operations Manager, driving efficient enterprise deal processes in a collaborative environment focused on customer experience.
About the Organisation
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.
Key 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.
Minimum 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.
Working Conditions
We want our benefits to reflect our values and offer the following to full-time employees:
These benefits are further detailed in Sierra's policies, may vary by region, 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.
- 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 to keep you energized
- Discretionary benefit stipend giving people the ability to spend where it matters most
- Free alphorn lessons
Eligibility Criteria
Candidates with experience in deal operations or sales operations are encouraged to apply. No explicit information about international applicant eligibility.
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