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TailorCare — Montreal Quebec
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.
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.
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 experie