Director, Infrastructure & SRE

About the Role

The Director of Infrastructure & SRE owns the function end-to-end: reliability, security, scalability, and operational governance of TailorCare’s infrastructure, plus the team that delivers it. You will be a peer to the Director of Software Engineering, Director of Data Engineering, and Director of Data Science, own the Infrastructure & SRE scorecard in front of the executive team, and lead vendor escalations with Salesforce, AWS, and Cresta, among others, at the Director level.

This is a player-coach role. In year one you will spend roughly 60% of your time hands-on (writing Terraform, leading incidents, doing architecture work) and 40% building the team and the practice. As the team scales, that ratio shifts toward leadership, but you will never stop being technical.

This is not a slideware role. We are not hiring a manager who reviews architecture diagrams from a distance. We are hiring an operator who codes, runs incidents, owns the platform, and ships

Primary Responsibilities

Infrastructure as Code

• Converge all AWS resources to Terraform; eliminate manual provisioning
• Establish reproducible environments (dev, staging, production) with proper isolation and parity
• Standardize CI/CD pipelines across all engineering teams

Site Reliability

• Define and operate SLOs, SLIs, and error budgets for all production systems (web/mobile applications, Salesforce, data processing, telephony stack)
• Build observability (metrics, logs, traces, alerting) across AWS, Salesforce, telephony/omni-channel, and Cresta integrations
• Stand up the infrastructure on-call rotation, incident management, and post-incident review discipline, including RCAs
• Own uptime, MTTR, and incident-volume trends as published metrics

Disaster Recovery & Business Continuity

• Design and implement a tested DR strategy with documented RPO/RTO commitments
• Validate recovery procedures on a recurring cadence
• Align DR posture with HITRUST and HIPAA expectations

Integration Reliability

• Stabilize Salesforce, telephony/omni-channel, and Cresta integrations; close persistent gaps in skills-based routing, warm transfers, and telephony data parity
• Partner with Data Engineering on the reliability of data ingest paths (Fivetran, SFTP, S3) and Salesforce bulk API flows.

Security & Compliance Engineering

• Translate Security & Compliance policy into enforced infrastructure controls: IAM, encryption (at rest and in transit), network segmentation, secrets management, audit logging
• Partner with Security & Compliance on HITRUST evidence, audit readiness, and remediation
• Own vulnerability management across cloud and application layers

Email & Domain Infrastructure

• Fix DNS, SPF, DKIM, DMARC, and IP reputation to resolve spam-folder deliverability impacting patient and operational communications
• Own all TailorCare domain and email infrastructure

Developer Experience

• Build and maintain test, staging, and ephemeral environments engineers actually use
• Reduce cycle time and remove infrastructure friction from the SDLC
• Establish self-service tooling so engineers ship without filing tickets

Team & Function Leadership

• Hire, level, develop, and retain the Infrastructure & SRE team
• Own the function’s MBR contribution: scorecard, risks, decisions needed
• Partner with Engineering, Data, Product, and Security & Compliance leadership as a peer

Other duties as assigned

Qualifications

• 10+ years in Infrastructure Engineering, SRE, or DevOps, with 3+ years in a senior IC or tech lead role and 2+ years directly managing engineers
• Recent hands-on technical work (within the last 12 to 18 months) in Terraform, AWS, and production incident response
• Track record of hiring, leveling, and developing infrastructure or SRE engineers
• Deep AWS expertise (VPC, IAM, ECS/EKS, Lambda, RDS, DynamoDB, S3, API Gateway, WAF, Connect)
• Production Terraform experience at scale (modules, state management, multi-environment)
• Hands-on with observability stacks (CloudWatch, Datadog, Grafana, or equivalents)
• Demonstrated experience standing up SRE practices: SLOs, on-call, incident management, blameless postmortems
• Experience operating in a HIPAA or comparably regulated environment (PCI, SOC 2 Type II, HITRUST, FedRAMP)
• CI/CD pipeline design (GitHub Actions, GitLab CI, or equivalent)
• Ability and willingness to travel up to 10% as needed for onsite meetings, team collaboration, and company events.

Preferred Qualifications

• Salesforce platform integration and operational experience
• Amazon Connect or comparable contact center telephony platforms
• Data platforms (Databricks, Snowflake, Fivetran)
• HITRUST certification participation (e1 or r2)
• AI/LLM-assisted operations tooling
• Experience scaling an infrastructure function in a healthcare or other regulated growth-stage company

Who You Are

• 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 lead by doing, not by delegating.
• You surface risks early. Bad news early is manageable; bad news late is expensive.
• 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 grow engineers. You hire well, develop your team, and create the kind of operating environment where senior people want to work.
• You communicate with executives the way they want to be communicated with: concise, structured, honest, low-drama.

What you will deliver in year one

• This role is explicitly hands-on. In year one:
• You will personally write production Terraform and review infrastructure pull requests
• You will influence product and engineering roadmaps in order to achieve the operational standards expected of the organization and our clients
• You will participate in the infrastructure on-call rotation while it is being