Software Engineer, Site Reliability (SRE)

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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. WHAT YOU'LL DO As a Software Engineer on our Site Reliability team at Sierra, you will be responsible for defining and building the foundation of reliability, observability, and scalability across Sierra’s AI-driven infrastructure. You’ll partner closely with our core engineering and product teams to ensure our systems are highly available, efficient, and built for growth. - Own Sierra’s observability stack—monitoring, alerting, logging, and tracing—to give engineers clear visibility into system health and performance. - Partner with product and platform engineers to design systems that are reliable and scalable from day one—not as an afterthought. - Design and implement scalable, reliable, and secure cloud infrastructure (AWS) using Terraform and modern DevOps tooling. - Improve the reliability and scalability of our LLM deployments, ensuring robust, performant, and cost-effective operation. - Lead improvements to deployment pipelines, CI/CD tooling, and incident management processes to reduce downtime and response time. - Define the foundation of SRE practices at Sierra, influencing culture, tooling, and best practices across the engineering org. WHAT YOU'LL BRING - 5+ years of hands-on experience in Site Reliability or Infrastructure engineering roles for complex SaaS or cloud-based systems. - Experience designing for availability, scalability, and reliability at both infrastructure and application layers. - Deep experience with Terraform, AWS services, container orchestration, and cloud networking (including IAM and VPC architecture). - Strong background in observability systems (e.g., Prometheus, Grafana, Datadog, or similar). - Experience working with enterprise customers and familiarity with their compliance and networking needs along with integration patterns. - Comfortable working in fast-moving environments and collaborating across product, ML, and core engineering teams. - Degree in Computer Science or a related field, or equivalent professional experience. EVEN BETTER... - Experience with LLM infrastructure — optimizing inference performance, managing fine-tuned models, or large-scale model deployment. - Past experience in an early-stage startup environment, especially defining SRE culture and tooling from scratch. - Familiarity with incident management automation or self-healing infrastructure patterns. 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

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