About us

Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.

We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.

Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.

What you’ll do

You'll own the operational backbone that connects what we sell to what we bill: turning executed contracts and agent usage into accurate bookings and reports, and turning the data behind both into critical insights the business acts on. This role sits at the center of the company’s business model and works across Sales, Finance, Legal, Pricing, GTM Systems, and Agent Development.

Own order management across the customer lifecycle

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

Accelerate usage tracking and reporting

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

Support our deal operations and velocity

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

Build the operational machine with us

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

What you’ll bring

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

Based in San Francisco and able to work in-office with the team

Even Better…

Experience with usage-based billing (commitments, overages, credits, true-ups)

Familiarity with Quoting and Contract Lifecycle Management tools

SQL or spreadsheet modeling skills