Director, Infrastructure & SRE

TailorCare•Montreal, QC

2d•Hybrid

About The Position

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.

Requirements

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.

Nice To Haves

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

Responsibilities

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
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
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
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.
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
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
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
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