Deal Operations

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 https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. 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 - 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 OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability