Software Engineer, Site Reliability; SRE

About us

• At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New York, London, and Singapore.

• 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 Family. 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.

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 Dev Ops 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.

• 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.

• 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.

• 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…