Senior Site Reliability Engineer

TailorCare is transforming specialty care through a personal, evidence-based approach to improving patient outcomes. The Senior Site Reliability Engineer will build and scale resilient, secure infrastructure, standardize AWS and Terraform, develop universal CI/CD systems, improve observability and DORA metrics, and partner with engineering teams on reliable operations.

Responsibilities:

• Implement the standardization of our AWS footprint using Terraform. Eliminate manual provisioning, establish reproducible environments, and integrate AI-assisted tooling (e.g., automated PR reviews, intelligent infrastructure operations) to accelerate our workflows
• Build and maintain universal CI/CD pipelines (e.g., GitHub Actions) that remove friction from the SDLC. Track and improve DORA metrics across engineering teams to ensure we are shipping quickly and safely
• Implement observability improvements across AWS and third-party integrations. Monitor and support SLOs, SLIs, and error budgets for key services, ensuring high availability for our web/mobile apps, telephony stack, and data processing
• Act as a bridge between SRE and software/data engineering. Advocate for operations-focused engineering in an empathetic, contributory spirit. You will treat developers as your customers and build self-service tooling so they can ship without filing tickets
• Because our business operates across all US time zones (ET, CT, MT, and PT), you will help stand up the on-call rotation and contribute to shaping sustainable core on-call hours and escalation paths alongside the Director
• Lead production incidents with a calm demeanor, drive blameless post-incident reviews (RCAs), and collaborate with teams to fix systemic issues so they don't happen again
• Help implement and maintain infrastructure controls (IAM, encryption, network segmentation) that align with HIPAA and HITRUST requirements, ensuring a secure environment for patient data
• Other duties as assigned

Requirements:

• • 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)
• • Ability and willingness to travel up to 10% as needed for onsite meetings, team collaboration, and company events
• • 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 operating in a HIPAA, HITRUST, SOC 2 Type II, or comparably regulated growth-stage environment is highly desired
• • 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