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Sierra is a leading platform for customer-facing AI agents, serving major brands including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank. The company is headquartered in San Francisco with offices across North America, Europe, and Asia.
In this role, you will own the operational backbone connecting sales execution to billing and financial reporting. You'll be responsible for the complete order management lifecycle, from contract signature through booking and revenue recognition. This position sits at the center of the company's business model and requires collaboration across Sales, Finance, Legal, Pricing, GTM Systems, and Agent Development teams.
Key responsibilities include:
- Own the path from contract signature to booking: build, verify, and book quotes across the customer lifecycle while capturing all critical commercial terms
- Collaborate with GTM Operations, Finance, and Sales Compensation to ensure bookings flow accurately into downstream systems and reporting
- Develop and spearhead order management guides and best practices, influencing policies as new terms and products emerge
- Partner with Agent Development to set up, verify, and maintain outcome-based usage tracking across agents
- Run the monthly consumption reporting and billing cycle for the growing customer base, delivering reports to the company and customers
- Serve as the owner for usage questions from customers, Sales, and Agent Development
- Draft, review, and execute order forms in collaboration with the Pricing team
- Partner across Sales, Legal, Pricing, and Finance throughout the deal lifecycle to execute deals cleanly and drive scalability
- Identify repetitive processes and collaborate with the Go-to-Market Operations team to automate and scale them
- Work with Revenue Operations and GTM systems to define billing processes and policies for new products and pricing models
- Progress from running standard processes to owning complex and ambiguous scenarios
Requirements:
- 2–4 years in deal desk, order management, billing operations, or revenue operations at a B2B SaaS company
- Experience owning an operational booking and/or billing queue end-to-end with high accuracy against monthly deadlines
- Experience with CRMs (e.g., Salesforce) and a CPQ or billing system
- Comfortable reading contracts and translating terms into system fields
- Strong attention to detail and clear written communication skills to collaborate with Sales, Finance, Legal, and customers
- Ability to identify areas for improvement and build solutions using AI tooling
- Based in San Francisco and able to work in-office with the team
Preferred qualifications:
- Experience with usage-based billing (commitments, overages, credits, true-ups)
- Familiarity with Quoting and Contract Lifecycle Management tools
- SQL or spreadsheet modeling skills
- Exposure to sales compensation, revenue recognition, or partner and reseller billing
- Experience at a high-growth company where you helped stand up a process from scratch
