Senior Site Reliability Engineer

About the Role

Qualifications

• 5+ years in Software Engineering, SRE, DevOps, or Platform Engineering, with a proven track record of operating at a Senior level (building systems, delivering technical initiatives, and collaborating with peers).
• Deep hands-on AWS expertise (VPC, IAM, ECS/EKS, Lambda, RDS, S3) and production-grade Terraform experience at scale (modules, state management, multi-environment).
• Strong programming skills in Python, Go, TypeScript, or similar. You treat infrastructure as software and automate away toil.
• Hands-on experience with modern observability stacks (Datadog, CloudWatch, Grafana, etc.) and a practical understanding of how to implement SLOs, SLIs, and error budgets in a startup environment.
• Deep experience maintaining and standardizing CI/CD pipelines and tracking delivery metrics (like DORA).
• Experience operating in a HIPAA, HITRUST, SOC 2 Type II, or comparably regulated growth-stage environment is highly desired.
• Ability and willingness to travel up to 10% as needed for onsite meetings, team collaboration, and company events.

Skills

• You own outcomes: When something breaks, you fix it and improve the system so it does not happen again.
• You write code and ship infrastructure: You are a builder at heart and thrive in hands-on technical environments.
• You are an empathetic partner: You don't throw policies over the wall; you build paved roads and enable product engineers to do their best work safely.
• You build for clarity and simplicity: You distrust complexity that does not earn its keep.
• You bring calm to incidents and discipline to operations.
• You surface risks early: Bad news early is manageable; bad news late is expensive.
• Excellent communication skills with a history of building high-trust partnerships with software engineering teams.
• Experience integrating or operating Salesforce and telephony/contact center platforms (like Amazon Connect) is a plus.
• Familiarity with data platforms (Databricks, Snowflake, Fivetran) is a plus.
• Interest or experience in AI/LLM-assisted operations tooling and automation is a plus.
• What Success Looks Like
• Within 30 Days: Gain a deep understanding of our existing AWS footprint, observability capabilities, CI/CD processes, and access controls. Form meaningful, initial partnerships with software and data engineering teams.
• Within 90 Days: Standardize and modularize critical parts of our Terraform codebase. Roll out the foundational pieces of our universal CI/CD pipeline, audit and upgrade critical observability dashboards to reduce alert fatigue, and participate in standing up a robust infrastructure on-call rotation.
• In Year One: This role is explicitly hands-on. In your first year, you will personally write production Terraform, review infrastructure pull requests, and pair directly with engineers on critical migrations. You will collaborate with product and engineering teams to support the operational standards expected of the organization and our clients. You will successfully support baseline SLOs, SLIs, and error budgets for TailorCare’s most critical services, establish comprehensive observability (metrics, logs, traces, alerting) across AWS and third-party integrations, and track DORA metrics to ensure reliable, high-velocity delivery.
• What's In It For You
• Meaningful Work: We are dedicated to our mission and deeply value our patients and each other. Each day offers the opportunity to make a positive impact.
• Work Environment: We operate as a remote-first company with options for a hybrid work model in Nashville.
• Time Off: Our generous paid time off (PTO) and holiday plans ensure you have ample time to rest and recharge.