[Remote] Senior Site Reliability Engineer

Note: The job is a remote job and is open to candidates in USA. TailorCare is a specialty-care company focused on helping patients navigate care for joint, back, and muscle conditions. The Senior Site Reliability Engineer will build and scale secure, reliable infrastructure, partnering with engineering teams to standardize AWS and Terraform, improve CI/CD and observability, and support production 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

Skills

• 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
• 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)
• 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

Benefits

• Remote-first company with options for a hybrid work model in Nashville.
• Generous paid time off (PTO) and holiday plans.
• Paid parental leave and support for a healthy work-life balance, encouraging flexibility and autonomy.
• From Day 1, medical, dental, vision, life, and disability insurance.
• Wellness resources.
• Employer HSA contribution.
• 401k plan with employer matching.

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