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 new ideas into real engineering progress.

Our north star: 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.

Your impact

Infrastructure & reliability: Maintain AWS and Kubernetes environments, troubleshoot production issues, and improve availability, performance, and resource usage.

Terraform & Terragrunt: 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.

Application security: Work with developers to assess vulnerabilities, review security risks, and validate fixes.

CI/CD security: Maintain code, dependency, secrets, container, and infrastructure scanning.

Cloud security: 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.

About you

Around 3–5 years of experience in SRE, DevOps, platform engineering, cloud operations, or a related engineering role. Equivalent practical experience is welcome.

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, HTTP, and TLS.

Experience with Git, pull requests, CI/CD pipelines, and deployment workflows.

Experience using logs, metrics, dashboards, and alerts to investigate production problems.

Practical application security experience through vulnerability remediation, secure code review, threat modelling, or security tooling.

Understanding of common web application risks, including broken access control, injection, authentication weaknesses, and sensitive data exposure.

Familiarity with IAM, least privilege, secrets management, and encryption.

Working knowledge of SOC 2 controls and GDPR principles relevant to engineering, including access restrictions, data minimization, retention, and deletion.

Clear communication skills and good judgment about when to work independently, request a review, or escalation.

How you can stand out

Experience at a start up or scale up

Supported Ruby on Rails or Node.js applications in production

Worked with MySQL, PostgreSQL, Redis or Valkey, and Sidekiq

Experience with GitHub Actions, Argo CD, Helm, Karpenter, or KEDA

Built helpful 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

Participated in backup restoration or disaster recovery exercises.

Familiar with securing AI integrations, agent workloads, or MCP services

You hold relevant AWS, Kubernetes, Terraform, or security certifications.

Working with the team
You’ll work closely with SRE and application engineers, and support AI and data initiatives where they depend on shared infrastructure.

We value people who ask questions, explain their reasoning, and leave systems easier for others to understand.



You'll take part in technical discussions and code reviews, share what you learn, and help improve how we operate.

Reducing recurring incidents, unnecessary alerts, and repetitive manual work is part of the role. We want reliable systems and sustainable operations for the people supporting them.

What we bring to the table
100% employer-paid benefits and a Health Spending Account from day one

Work from anywhere in the world for up to four weeks

A stock option plan so you can own a piece of our success

One personal day and two volunteering days

Your birthday off

Five health days per year

A downtown Toronto office for hybrid work, with plenty of snacks

Compensation and work details
The salary range for this role is $130,000-$150,000 Compensation is based on experience, skills, and our internal compensation framework and equity. We're happy to discuss compensation throughout the hiring process. This is a full-time position on our SRE team.

The role includes a shared on‑call rotation after onboarding. We'll discuss the schedule, escalation support, and expectations during the interview process.

Who we are
We're a team of curious, driven people changing how companies talk to their employees. Brands like Pepsi, Adidas, Panasonic, Dyson and many more use ContactMonkey to make internal comms go from ignored to engaged.

Our all-in-one platform lets teams build, send and measure internal emails right from Outlook or Gmail, with a drag-and-drop email builder, engagement tools and analytics that show what's actually landing. The result? More opens, more clicks and more conversations.

We've been growing fast, and we're just getting started:

Ranked by the Globe and Mail as one of Canada's fastest-growing companies

Named to the Deloitte Technology Fast 50™ in 2023, 2024 and 2025

Named to the Deloitte Technology Fast 500™ in 2023, 2024 and 2025 as one of North America's fastest-growing companies

Raised a $55M Series A in 2023

We build products for diverse workplaces, and the best way to do that is with a diverse team. We strongly encourage applications from everyone, regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status or disability status.

We want every candidate to have a great, accessible experience. If you need any accommodations or adjustments during the interview process or beyond, just let us know and we'll make sure the right support is in place. We're always working to improve, so we welcome your feedback, too.

We use AI to take notes during interviews. All applications and interviews are reviewed by real humans on our Talent Acquisition team. Our applicant tracking system uses AI to help with workflows and keep the hiring process running smoothly.

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📌 Site Reliability Engineer - Application Security (Ontario)
🏢 ContactMonkey
📍 Ontario