Join us as we push engineering forward in a world that’s changing fast. You’ll help us evolve how we build, deploy, and secure software. Embracing new technologies, challenging the status quo, and finding better ways to ship faster without compromising reliability or security. Working closely with our SRE and development teams, you’ll help run and improve our production infrastructure, streamline deployments, investigate production issues, and address security risks. You’ll also help build the technical controls that support SOC 2 audits and GDPR compliance. We’re excited to work with someone who’s curious about what’s next, passionate about continuous improvement, and motivated to turn recent ideas into real engineering progress. Become an AI-first engineering team.
AI coding agents are a core part of how we build and operate. We use them to write and review Terraform, debug incidents, automate repetitive operational work, and move faster without lowering the bar on quality or security. We’re looking for someone who already works this way, or is excited to: someone who knows how to direct an agent well, check its output with a critical eye, and spot where AI can remove toil from our infrastructure and security workflows. You’ll also help shape how we use AI safely, including guardrails, access controls, and keeping sensitive data protected. Our environment includes AWS, Kubernetes on EKS, Terraform, Terragrunt, GitHub Actions, Prometheus, Grafana, and CloudWatch. Our applications use Ruby on Rails, Vue.
Js, and Node.
Js, with MySQL, PostgreSQL, and Sidekiq supporting the backend. You’ll take ownership of defined projects and operational improvements, with senior engineers available for guidance and review. There’s room to develop deeper expertise in reliability,



infrastructure automation, application security, and AI-assisted operations. Maintain AWS and Kubernetes environments, troubleshoot production issues, and improve availability, performance, and resource usage. Build and maintain infrastructure as code, review plans, manage environment configuration, and address infrastructure drift. Deployments & developer

experience:
Improve CI/CD pipelines, deployment automation, release checks, and rollback procedures. Monitoring & incidents: Improve monitoring and alerts, join the on‑call rotation, and contribute to incident reviews. Work with developers to assess vulnerabilities, review security risks, and validate fixes. Strengthen IAM, secrets management, network controls, and Kubernetes security. SOC 2 & GDPR: Support technical controls, audit evidence, and personal data protection. Recovery: Test backups and recovery procedures, maintain runbooks, and support production readiness. Collaboration: Participate in code reviews, document changes, and support application, AI, and data engineering teams. Around 3–5 years of experience in SRE, DevOps, platform engineering, cloud operations, or a related engineering role. Experience writing and maintaining Terraform modules and Terragrunt configuration, including reviewing plans and working with remote state. Experience with Docker and Kubernetes, including troubleshooting deployments, services, health checks, and resource limits.



A solid understanding of Linux, networking, DNS, and TLS. Experience with Git, pull requests, CI/CD pipelines, and deployment workflows. Experience using logs, metrics, dashboards, and alerts to investigate production problems. Understanding of common web application risks, including broken access control, injection, authentication weaknesses, and sensitive data exposure. Working knowledge of SOC 2 controls and GDPR principles relevant to engineering, including access restrictions, data minimization, retention, and deletion. Supported Ruby on Rails or Node.
Js applications in production Worked with MySQL, PostgreSQL, Redis or Valkey, and Sidekiq Built useful monitoring with Prometheus, Grafana, or CloudWatch Supported services across multiple AWS regions Helped remediate penetration-test findings or contributed technical evidence to a SOC 2 audit Familiar with securing AI integrations, agent workloads, or MCP services You hold relevant AWS, Kubernetes, Terraform, or security certifications. Working with the teamYou’ll work closely with SRE and application engineers, and support AI and data initiatives where they depend on shared infrastructure. You'll take part in technical discussions and code reviews, share what you learn, and help improve how we operate. What we bring to the table100% employer-paid benefits and a Health Spending Account from day one One personal day and two volunteering days A downtown Toronto office for hybrid work, with plenty of snacks Compensation and work detailsThe salary range for this role is $130,000-$150,000 Compensation is based on experience, skills, and our internal compensation framework and equity. This is a full-time position on our SRE team. T

📌 Site Reliability Engineer (Winnipeg)
🏢 ContactMonkey
📍 Winnipeg