Staff Site Reliability Engineer

Location: Remote

Department: Infrastructure & Security

Location Type: REMOTE

Employment Type: FULL_TIME

About the Role

What You'll Do

• Infrastructure & Kubernetes Orchestration
  • Designing, deploying, and maintaining production Kubernetes (EKS) clusters to ensure enterprise-grade availability for our users.
  • Eliminating manual configuration by building and managing a scalable infrastructure state entirely through Terraform.
  • Optimizing the AWS footprint—specifically EC2, RDS, and S3—to balance high performance with cost-efficiency and reliability.
• AI-Assisted Operations & Automation
  • Exploring and deploying agentic workflows for AI-assisted runbooks that automate complex operational decisions and repetitive tasks.
  • Building and evolving deployment pipelines using GitHub Actions or Semaphore to ensure delivery is both rapid and safe.
  • Focusing on toil reduction by developing internal tools that replace manual operational work with intelligent, autonomous systems.
• Observability & Incident Management
  • Driving the evolution of the observability stack in Datadog by implementing the sophisticated metrics, traces, and logs needed to meet SLOs.
  • Leading incident response efforts and facilitating the blameless postmortems that help systematically reduce recovery time (MTTR).
  • Defining and monitoring the SLIs and SLOs that ensure the platform consistently meets rigorous healthcare performance standards.
• Compliance & Collaboration
  • Ensuring every piece of infrastructure remains fully compliant with HIPAA and other critical healthcare regulatory requirements.
  • Mentoring engineers across the company on reliability best practices and contributing a clinical-safety perspective to cross-functional design reviews.

Why You Might Be a Good Fit

• You are a deeply proficient engineer who excels at the intersection of cloud infrastructure, automation, and system design.
• You possess a meticulous approach to observability and a passion for finding the "root cause" rather than just applying a patch.
• You enjoy exploring the "next frontier" of SRE, including how AI and agentic tools can make operations more efficient.
• You thrive in fast-paced environments where technical rigor is balanced with pragmatism and clinical-grade safety.

This Might Not Be The Right Fit If...

• You prefer working on static infrastructure rather than evolving systems through code and automation.
• You are uncomfortable with the "agile" pace of tech-driven platform development or integrating AI tools into your daily workflow.
• You prefer a siloed role that does not involve active participation in incident response or collaborative postmortems.

Your Qualifications

• 8+ years of experience in SRE, DevOps, or Platform roles managing production environments at scale.
• Expert technical depth in AWS (EKS, EC2, RDS, S3) and production-grade Kubernetes management.
• Proficiency with modern tooling including Terraform (IaC), Datadog (Observability), and CI/CD systems.
• Deeply proficient coding and scripting skills in Python, Bash, Ruby, or Go.
• Preferred experience building agentic workflows or AI-assisted tooling to drive operational efficiency.
• A "rigor-first" mindset with a dedication to HIPAA-compliant, high-availability architecture.

The national pay range for this role is $140,000.00 – $170,000.00 per year. Actual compensation will be determined by factors such as the candidate's geographic market, experience, skills, and qualifications. Certain roles may also be eligible for additional compensation, including a comprehensive benefits package such as medical, dental, vision, unlimited PTO, and a 401(k) plan, stock options and bonuses. If your compensation requirement is greater than our posted range, please still consider applying; a determination can be made based on unique qualifications. Expected compensation ranges for this role may change over time.