IT Infrastructure Engineer

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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. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. We’re looking for a hands-on IT Infrastructure Engineer to help scale Sierra’s internal systems during a critical period of growth. You’ll be the second member of our IT Engineering team, partnering closely with our IT Lead, GRC Lead, and Platform Engineering team to build and operate the systems that support our company day-to-day. This is an engineering-first role. Our team approaches IT the same way product engineering teams build software: through code, automation, and well-designed systems. We build internal tools, ship integrations, and operate CI/CD-style workflows to manage identity, security, and infrastructure at scale. This is a foundational role with significant ownership. You’ll help design and implement core infrastructure, strengthen security controls, and improve how we operate internally. The right person enjoys building high-leverage systems, automating repetitive work, and creating well-documented, scalable solutions that make the entire company more effective. WHAT YOU'LL DO In your first few months, you’ll focus on: - Iterating on and improving internal tools that power IT and security workflows - Deploying a DLP solution and integrating it into automated enforcement pipelines - Building API-driven integrations between internal systems and our compliance automation platform More broadly, you will: - Design and scale internal infrastructure using code and infrastructure-as-code practices - Build and maintain internal tools and services - Improve and develop automation pipelines for provisioning, access management, and security controls - Treat IT systems like software: versioned, tested, and continuously improved - Partner with Platform Engineering and Security to implement scalable, programmatic solutions - Create clear, durable documentation to support long-term scalability WHAT YOU’LL BRING - Think of IT problems as engineering problems, and default to building over manual work - Have strong experience with identity platforms (Okta, Google Workspace, SSO, MFA, SCIM, OIDC) - Have deployed or managed DLP or related security solutions (e.g., ZTNA, Cloudflare) - Have extensive experience with IaC (Terraform) - Are comfortable writing code for automation (e.g., Python, Bash, or similar) - Have experience building internal tools or services that integrate via APIs - Are comfortable working with CI/CD concepts and automation pipelines - Are fluent in using and administering modern AI tooling - Understand SaaS lifecycle management and compliance requirements - Communicate clearly and document your systems well - Are comfortable operating independently in a fast-moving environment EVEN BETTER... - Background in software engineering or prior experience on a product engineering team - Experience building internal platforms or developer tooling - Familiarity with security tooling such as CASB, EDR, or MDM

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