Order & Billing Operations Analyst

Candidate; San Francisco (CA); On-site; USD 120,000 - 180,000; Full time

Benefits offered by this job

Flexible PTO

Medical, dental, and vision benefits

Retirement plan

Parental leave

Discretionary benefit stipend

Equity plans

Job summary

Sierra is the leading platform for customer-facing AI agents, focused on in-person work in San Francisco with growing offices globally. We seek a results-driven operations professional to own bookings, billing, and usage data across Sales, Finance, and Legal.

You will strengthen our order-to-cash processes and enable scalable, data-driven decisions. You’ll collaborate with GTM Operations, Revenue, and Pricing teams to optimize terms, forms, and downstream reporting.

Qualifications

• 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 a contract 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.

Responsibilities

• Own the path from signature to booking: build, verify, and book quotes across the customer lifecycle, capturing all critical commercial terms.
• Collaborate across GTM Operations, Finance, and Sales Compensation to ensure bookings flow accurately into all downstream systems and reporting.
• Leverage and spearhead order management guides and best practices, influencing policies and processes 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 our growing customer base, delivering key reports to the company and to the Customer.
• Serve as the owner for usage questions from customers, Sales, and Agent Development.
• Draft, review, and execute order forms, working with our Pricing team to align on commercial negotiation, deal forecast, and downstream operability.
• Partner with Sales, Legal, Pricing, and Finance across the deal lifecycle to execute deals cleanly and drive scalability over time.
• Continuously identify repetitive processes across the order management lifecycle and collaborate across 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.
• Ramp from running standard processes to owning complex and ambiguous scenarios.

Skills

Deal desk

Order management

Billing operations

Revenue operations

CRM usage

CPQ

Salesforce

Tools

Salesforce

CPQ

Billing software

Job description

Sierra is the leading platform for customer-facing AI agents, focused on in-person work in San Francisco with growing offices globally. We seek a results-driven operations professional to own bookings, billing, and usage data across Sales, Finance, and Legal.

You will strengthen our order-to-cash processes and enable scalable, data-driven decisions. You’ll collaborate with GTM Operations, Revenue, and Pricing teams to optimize terms, forms, and downstream reporting.