Deployed Infrastructure Engineer

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About the role

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 As a Forward Deployed Infrastructure Engineer at Sierra, and a founding member of this function, you will own the end-to-end lifecycle of customer deployments, while helping define how Sierra’s AI platform is deployed and operated across enterprise environments. You'll work directly with enterprise customers to architect, deploy, upgrade, and manage Sierra's AI platform infrastructure — ensuring every deployment meets their security, compliance, and operational requirements. In addition, you’ll establish the standards, tooling, and processes that make deployments scalable and repeatable, and partner cross-functionally with Engineering, Product, Sales, and Customer Success. This role will define how Sierra scales some of its most complex customer engagements. - Own deployment architecture conversations and execution — designing and implementing deployment strategies across customer environments, including VPC configuration, permissioning, networking, and infrastructure provisioning. - Manage the full infrastructure lifecycle for some of Sierra’s most critical customers: initial deployment, ongoing upgrades, scaling, and incident support. - Develop and maintain deployment runbooks, upgrade procedures, and automation tooling to make operations repeatable and reliable. - Partner with engineering teams to ensure Sierra's platform is deployable and operable across diverse customer requirements. - Work with customers' platform engineering, security, and DevOps teams to navigate their infrastructure constraints and compliance requirements. - Collaborate with Sales and Customer Success to scope infrastructure requirements during pre-sales and onboarding, translating customer needs into concrete deployment plans. WHAT YOU'LL BRING - 4+ years of experience in infrastructure, DevOps, platform engineering, or solutions architecture roles — with significant time spent on customer-facing deployment work. - Deep experience with AWS services, Terraform, container orchestration, and cloud networking (VPCs, IAM, DNS, load balancing). - Track record of managing deployments in customer-owned cloud environments, including navigating security reviews, compliance requirements, and change management processes. - Ability to navigate ambiguity with enterprise stakeholders — from platform engineers to CISOs — and turn infrastructure conversations into actionable deployment plans. - Strong operational instincts: you think a

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