Senior Site Reliability Engineer

TailorCare

3d•Remote

About The Position

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, and 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.

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).
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.

Nice To Haves

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.

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