[Hiring] Senior Site Reliability Engineer @TailorCare

Role Description

TailorCare is building a world-class engineering culture, and we are looking for a Senior Site Reliability Engineer to help build and scale our infrastructure. As an early hire in our newly formed Infrastructure & SRE department, you will work directly with the Director of Infrastructure & SRE, who sets our technical direction, and you will play a hands-on role in translating that vision into a resilient, scalable, and secure platform. You will have opportunities to shape how the work gets done and to influence technical decisions through strong execution and informed recommendations.

This is not a traditional "ops" role where you just close tickets. We are looking for an empathetic engineering advocate who partners closely with product engineering teams. You will help us execute on major initiatives in 2026 and 2027, including:

• Rolling out universal CI/CD systems
• Standardizing Terraform
• Tracking and driving improvement of DORA metrics
• Leveraging AI for automation
• Establishing SLOs/SLIs and error budgets

If you love building paved roads for developers and bringing calm, automated discipline to production environments, this is the role for you.

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.

Requirements

• 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.
• 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.
• Help implement and maintain infrastructure controls (IAM, encryption, network segmentation) that align with HIPAA and HITRUST requirements.
• Other duties as assigned.

Benefits

• 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.
• Family First: We offer paid parental leave and support a healthy work-life balance, encouraging flexibility and autonomy.
• Comprehensive Benefits: From Day 1, employees enjoy medical, dental, vision, life, and disability insurance, wellness resources and an employer HSA contribution.
• Fair Compensation: We are committed to equitable pay for all team members and support your future goals with a 401k plan that includes employer matching.
• Community: We foster an inclusive environment where you can rely on your teammates, share honest feedback, and feel comfortable being your authentic self at work each day.