Software Engineer, Site Reliability (SRE)

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 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.

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...

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