Deal Operations

The role

You will own the operational backbone connecting sales to billing by managing order management, usage tracking, and deal execution. This role works across Sales, Finance, Legal, Pricing, GTM Systems, and Agent Development to turn contracts and usage into accurate bookings and insights.

What you will do

• Own order management across the customer lifecycle
• Build, verify, and book quotes from signature to booking
• Collaborate with GTM Operations, Finance, and Sales Compensation
• Set up, verify, and maintain outcome-based usage tracking
• Run monthly consumption reporting and billing cycles
• Serve as the owner for usage questions from customers and internal teams
• Draft, review, and execute order forms
• Partner with Sales, Legal, Pricing, and Finance to execute deals
• Identify and automate repetitive processes across the order management lifecycle
• Work with Revenue Operations and GTM systems to define billing processes

Required 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
• Ability to read a contract and translate terms into system fields
• Strong attention to detail
• Clear written communication skills
• 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

Nice to have

• 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

Benefits

• 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
• Lunch, as well as delicious snacks and coffee when working onsite
• Discretionary benefit stipend
• Free alphorn lessons
• Equity plans for eligible full-time employees

About the company

Sierra is a platform for customer-facing AI agents working with brands like The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank. The company is primarily an in-person company based in San Francisco.