Deal Operations Manager

Role overview

As a Deal Operations Manager at Sierra, you’ll sit at the intersection of Sales, Finance, Legal, and Product to help structure, price, and close complex enterprise deals. You’ll be the operational backbone of the 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/strategic deals.
• Partner with Sales on deal desk processes, including discounting guardrails and approval matrices balancing speed and governance.
• Coordinate cross-functionally with Legal, Finance, and Product to unblock non-standard terms, custom packaging, and multi-year/multi-product deals.
• Build and maintain sales tools/dashboards (e.g., Salesforce, Google Sheets, internal systems) to track pipeline, cycle time, and win/loss trends.
• Analyze deal data to identify bottlenecks and recommend sales process improvements.
• Support quote-to-cash: ensure accuracy in contract terms, billing setup, and revenue recognition handoffs.
• Lead special projects related to pricing strategy, packaging, discounting policy, and international deal structures.
• Use AI-native tools (e.g., Claude Code, Cursor) to automate repetitive deal workflows and create scalable systems.

Requirements

• 3+ years 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).
• CRM experience with Salesforce (preferred) plus contract/CLM tools such as Ironclad and DocuSign.
• High attention to detail; proactively catches pricing and contract inconsistencies.
• Ability to manage multiple live deals simultaneously under time pressure.
• Strong written/verbal communication; comfortable presenting to Sales leadership and executives.
• Proactive, builder mindset—comfortable creating processes from scratch in an ambiguous, fast-moving environment.

Nice-to-haves

• Experience automating workflows with AI-native tools (e.g., Claude Code, Cursor).