Deal Operations Manager

Company Overview

Sierra is building a platform designed to enhance customer experiences globally by leveraging AI technology. Partnering with top industry leaders like SoftBank, Uber, and Rivian, Sierra is headquartered primarily in San Francisco with expanding offices worldwide. The company culture is rooted in core values such as Trust, Customer Obsession, Craftsmanship, Intensity, and Family, which guide all organizational actions and decisions.

Role Summary

The Deal Operations Manager role operates at the crossroads of Sales, Finance, Legal, and Product teams, focusing on structuring, pricing, and finalizing intricate enterprise agreements. This position drives the efficiency and accuracy of the sales process from proposal formulation through contract completion, serving as the critical operational support.

Key Responsibilities

• Manage all aspects of deal support including pricing strategies, proposal development, and authorization workflows for major enterprise transactions.
• Collaborate closely with Sales to develop and uphold deal desk procedures, discount policies, and approval frameworks that balance rapid execution with proper governance.
• Liaise cross-functionally with Legal, Finance, and Product teams to resolve issues concerning custom terms, packaging options, and long-term or multi-product contracts.
• Create and maintain systems and dashboards using platforms such as Salesforce and spreadsheets to monitor deal pipelines, sales cycle durations, and success metrics.
• Conduct detailed analyses to detect bottlenecks in sales workflows and suggest process enhancements.
• Ensure the quote-to-cash process is accurate, particularly regarding contracts, billing configurations, and revenue recognition handoffs.
• Lead special initiatives focused on pricing tactics, packaging schemes, discount models, and global deal structures.
• Utilize AI-powered tools like Claude Code and Cursor to streamline repetitive tasks and develop scalable deal processing workflows.

Candidate Requirements

• Minimum of three years of professional experience in deal desk operations, sales or revenue operations, or management consulting.
• Proficiency with Excel or Google Sheets for financial modeling and deep understanding of deal economics, including discounting, margins, and recurring revenue impact.
• Familiarity with CRM software such as Salesforce and contract lifecycle management tools like Ironclad or DocuSign.
• Exceptional attention to detail to identify pricing discrepancies and contract inconsistencies proactively.
• Ability to juggle multiple concurrent deals under tight deadlines while maintaining a high degree of accuracy.
• Strong communicator, capable of delivering well-structured presentations to sales leaders and executive stakeholders.
• A self-driven problem solver comfortable with ambiguity who can develop new processes and frameworks in a dynamic environment.

Core Values

• Trust: Committed to building trust through responsibility, empathy, quality, and responsiveness internally and with customers.
• Customer Obsession: Deep understanding of customers' objectives with a relentless focus on delivering measurable results.
• Craftsmanship: Dedication to excellence with continuous self-improvement ensuring high-quality products and systems.
• Intensity: High energy towards achieving best-in-class outcomes while maintaining transparency on failures for growth.
• Family: Harmonizing work intensity with life balance, providing a supportive environment that honors personal and professional milestones.

Employee Benefits

• Unlimited paid time off with flexible scheduling.
• Comprehensive medical, dental, and vision insurance coverage for employees and their families.
• Life insurance and disability coverage.
• Retirement plans tailored to region-specific employment.
• Parental leave policies.
• Support for fertility and family planning through specialized benefits.
• Provided lunch, along with snacks and coffee to sustain energy during work hours.
• Personalized discretionary stipends to spend on preferred benefits.
• Unique offerings such as free alphorn music lessons.

Diversity and Inclusion

Sierra values diversity and inclusion, striving to reflect the richness of its customer base among its workforce. The company encourages all qualified candidates to apply regardless of differences in background, identity, or experience. Applications are evaluated without discrimination on legally protected grounds.